63 Kissimmee Vacation Rentals With Private Pool

kissimmee vacation rentals with private pool
Seema
Contributing Writer
Updated
| 15 min read

Kissimmee, Florida is perfect for family vacations at theme parks, a getaway with friends, or a romantic outing with your partner. This family-friendly city is within a few minutes’ drive from Walt Disney World Resort. When you have had your fill of the Disney magic, there’s also Universal Orlando Resort and SeaWorld Orlando nearby. Apart from theme parks, there’s a lot on offer for nature and adventure lovers. You can zip through treetops and glide across the headwaters of the Everglades, get a close view of alligators in the Airboat and Gator Park, or soar over the lush landscape in a hot air balloon. If shopping and lounging in cafes is more your style, there are several malls, including The Florida Mall and The Mall at Millenia, with premium designer boutiques. You can feast at the top restaurants in the city as well.

Are you planning to visit Kissimmee? Make sure to book relaxing accommodation for your stay. Scroll down for a list of Kissimmee vacation rentals with private pool.

Hidden gems:

  • Boggy Creek Airboat Adventures: Here, you can explore a scenic 32-acre (12.95-hectare) park with beautiful lighted pathways by the lake. Take a thrilling airboat ride to spot Florida’s reptiles, wander through Lily’s Butterfly Garden, and try your luck at panning for gems and fossils. Also, don’t forget to stop by the authentic Native American Village to learn more about history.

  • The Paddling Center at Shingle Creek: Kayak, canoe, or paddleboard through a peaceful cypress forest. They offer rentals and guided eco-tours, making it easy to explore Florida’s natural beauty. Plus, you’re just a short distance from Walt Disney World and other well-known attractions.

We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to private pool. The image galleries get refreshed with the latest updates regularly. They were last updated on October 25, 2025.

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All Beach Access (1) Budget Friendly (3) Budget Friendly (10) Convenient Location (8) Convenient Location (2) Couple Travel (1)

1. Beautiful seven-bedroom lake house (from USD 635)

Highlights Family Friendly Waterfront View

Best for: Nature lovers, families with kids and infants, reunions

Live in a sparkling clean, beautiful lakefront home that can accommodate a gathering as large as 16 people. It is conveniently located near theme parks, malls, and restaurants. There are seven bedrooms, a spacious living room, a kitchen, a games room, as well as access to the resort’s community pool, a community hot tub, a gym, sports facilities, barbeque, and a picnic area. All the beds have comfy memory foam mattresses. There’s a beautiful lake view and free WiFi. At this Airbnb in Kissimmee, Florida with a private pool, you also have a spa with heating.

Kissimmee, Florida, United States
405 reviews   Wifi Available
ENTIRE HOME 10 Beds 16 Guests 7 Bedrooms 4 Bathrooms

Accommodates: 16

Top guest reviews
Host:
great hosts and a wonderful property
the hosts were quick to respond and very pleasant
the owners were very responsive anytime i contacted them they answered right away
amazing property and wonderful responsive hosts
usually host write you the day of just to make sure you have key points
Location:
great location about 25 minutes drive to disney world universal studios and the airport
the location was perfect for our needs
the location is great and there is a great path to walk around the lake
would definitely recommend everything is fairly close and the house is great
the house was beautiful with the perfect location
Cleanliness:
very clean lots of space
bathrooms were clean but need a much deeper clean in the shower windows
we found this home very clean and well furnished
the bedding was fresh & clean
very beautiful clean and modern house to stay with friends and family
Amenities & Room:
plenty of room a wonderful pool and deck with a view of a beautiful lake
the sunrise from the pool looking out over the lake is beautiful
kids loved the pool and the area has amazing amenities such as playground and tons of ducks
loved all the different rooms - plenty of space for everyone
loved the many bathroom and game room
Read more reviews

2. Luxurious home in a gated community (from USD 1240)

Highlights Pet Friendly Work Travel Family Friendly Luxury

Best for: Pet parents, workationers, families with kids and infants, reunions

Professionally decorated and appointed with luxurious amenities, this beautiful home is located in the gated community of Veranda Palms. Ideal for large groups of up to 16 people, it has six luxe bedrooms, four and a half bathrooms, three gorgeous living rooms, a game room, two dining rooms, a modern kitchen, and more. Outside, you can relax in your private pool or enjoy a relaxing soak in the spa. Prepare barbecue meals for everyone that you can enjoy at the alfresco dining area. All famous theme parks are a short drive away from this house.

Kissimmee, Florida, United States
459 reviews   Airbnb superhost icon Superhost Wifi Available
Entire villa 11 Beds 16 Guests 7 Bedrooms 4 Bathrooms

Accommodates: 16

Top guest reviews
Host:
hosts were great
also the host was great
and the host douglas was very helpful
awesome property with amazing hosts
douglas the host was great great response time and very considerate and helpful
Location:
location was great and quiet neighborhood close to everything
the location is wonderful
great location and comfortable house
location is great as well
also an ideal location close to disney
Cleanliness:
the house is beautiful clean and modern
the house was great clean and spacious
the rooms were very clean and comfortable
very clean spacious and up to date
pool is fun and the house was very clean
Amenities & Room:
the amenities like the pool game room and the grill are what most impressed me
the game room kept my kids entertained playing pool and air hockey
there was a very fierce storm with huge hailstones which dashed the screen around the pool
the kids loved the pool and the jacuzzi and the large game room
lots of space and game room and pool loved so much
Read more reviews

3. Gorgeous four-bedroom townhome in Storey Lake Resort (from USD 664)

airbnb
Source: airbnb
Highlights Luxury Family Friendly Good Location

Best for: Luxury travelers, families with kids and infants, group stays

A brand new luxury townhouse close to Disney World, Universal Studios, Sea World, numerous outlet malls, Orlando attractions, Disney Springs, restaurants, and dining. There’s enough space for eight guests with four bedrooms, three baths, a large living room, and a state of the art kitchen. What’s special about this house is the beautiful decor with cozy furnishings. There’s a private pool with lanai screens where you can swim and relax after a day of sightseeing. Children can also head to the clubhouse with a large pool, a water slide, and a long lazy river to play and splash about. Families will surely enjoy this Airbnb in Kissimmee, Florida with a pool.

Kissimmee, Florida, United States
58 reviews   Wifi Available
Entire townhouse 6 Beds 8 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 8

Top guest reviews
Host:
thank you for being great hosts
clint was ultra-responsive and ready to help with any questions or concerns
excellent communications from the host
Location:
great location and really spacious
this place was great location is great
fantastic place and great location
great location close to parks and groceries
it’s just a short nice walk to the clubhouse
Cleanliness:
very clean and spacious
clean and beautiful
very clean and quiet neighborhood
beautiful house clean and comfortable
it was very clean and had everything we needed
Amenities & Room:
the washer/dryer refrigerator and small appliances were nice and the kitchen well stocked with supplies
the villa is huge with a beautiful view from pool area looking onto a lake
great for families with a fully equipped kitchen and three full bathrooms
the beds were comfortable and the kitchen was spacey
the place was tip-top and very comfortable
Read more reviews

4. Two-storey home in Lake Berkley Resort (from USD 559)

Highlights Family Friendly Waterfront

Best for: Outdoor enthusiasts, reunions, families with kids

Book this great two-storey accommodation to spend relaxing time indoors. Else, you can head out to the private, screened pool to dip into its cool water. This can even be heated on prior notice at additional charges. Alternatively, you can lounge poolside and soak in the sunshine.

In addition to the private facilities, you can also use the resort’s shared conveniences. These include the communal pool, hot tub and basketball court among others. These are all excellent spots to mingle with the other guests staying at the resort, so you can head out to socialize a bit.

Note that quiet hours are to be observed between 10pm and 8am by guests staying in the rental unit.

Kissimmee, Florida, United States
74 reviews   Wifi Available
Entire villa 7 Beds 12 Guests 6 Bedrooms 3 Bathrooms

Accommodates: 12

Top guest reviews
Host:
the host phillip was phenomenal and super quick to respond and very friendly
phillip was very accommodating for our large party last minute extremely responsive
the pool was amazing and the owner was extremely responsive
a good sized house for our big group and the host was extremely responsive
great house and a lot of fun owner is great and super cooperative
Location:
location was great
great location and great value
great location and excellent value for the price
great location the beds are very comfortable
this place is beautiful and near all kinds of family activities
Cleanliness:
we arrived at the house and everything was clean and organized
needed a good all around deep clean and ac would not cool the house adequately
Read more reviews

5. New home with themed rooms (from USD 1535)

Highlights Luxury Family Friendly Unique Theme

Best for: Luxury travelers, families with kids and infants, reunions

Book this brand-new, charming vacation retreat and spend a memorable time with your loved ones. At this multi-storey home, you can spend hours unwinding in the living room, else you can head to the equipped games room and challenge your buddies to a bit of competition. You will find a PlayStation, pool table and several other games here.

Alternatively, you can dive in the private pool and swim a few lengths. Right by the pool, you will also find a private hot tub, which is ideal for a calming soak. If you are booking this place for five nights or more, you can also opt to have the pool heated for an additional fee.

Note that quiet hours are to be observed after 10pm.

Kissimmee, Florida, United States
133 reviews   Airbnb superhost icon Superhost Wifi Available
Entire villa 8 Beds 14 Guests 6 Bedrooms 5 Bathrooms

Accommodates: 14

Top guest reviews
Host:
the host were amazing they responded immediately anytime we reached out
Location:
walmart super store is 2-3 min up the street
good location lots of places to eat as well as being close to many attractions in orlando
the location was good not far from the parks
this is a fantastic place to stay
Cleanliness:
our host was the best at communication and the property was very clean
bathrooms in each room everything was so neat and clean
Amenities & Room:
the game room made it so easy to keep all the kids (all ages) entertained
we loved the hot tub pool and game room
the house was absolutely immaculate upon arrival with thoughtful ambient lighting and dining table set
the house has many rooms and the game room is amazing
Read more reviews

6. Fully furnished house near major attractions (from USD 938)

Highlights Luxury Family Friendly

Best for: Luxury travelers, families with kids and infants, group stays

Book this home if you want to stay near Orlando’s main attractions. This place is within a 25-minute drive from several major tourist attractions in Orlando, plus it is the perfect base to relax after all the activity.

Lounging by the pool and soaking in the sunshine is one option or you can plunge into the pool for a refreshing swim session. The pool can be heated for additional fees, so you can enjoy a soothing dip as well. You can prepare a full-fledged meal and dine indoors, or consider paying an extra fee to fire up the barbecue to savour your meal alfresco.

Kissimmee, Florida, United States
90 reviews   Airbnb superhost icon Superhost Wifi Available
ENTIRE HOME 4 Beds 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Host:
eric is a great host
eric was an amazing host he went above and beyond to make our stay one to remember
i throughly enjoyed my visit and eric was a wonderful host
thank you eric for hosting us
eric was timely and kind in his responses
Location:
very close to so many attractions
location was great for all the parks and felt very safe as it's located in a quiet area
close to the parks and shopping will definitely recommend
fantastic stay the location was close & convenient for visiting all the disney parks + universal studios
the location was great and easy to navigate to the parks or restaurants quickly
Cleanliness:
the house is very clean and spacious
it is very clean house with vey amazing touch
the house was very clean and had everything we needed
the house was clean and the kids really enjoyed the pool
me and my family enjoy our stay at this wonderful spot this place was spacious and clean
Amenities & Room:
eric was a great communicator and the pool was perfect
the temperature of the pool was perfect for those cool evenings
Read more reviews

7. Gorgeous villa for a large group (from USD 656)

Highlights Luxury Family Friendly Unique Theme

Best for: Luxury travelers, group stays, families with kids

This is a great villa in Kissimmee for a big family reunion or a gathering of friends. The highlight of the property is a unique Batman-themed game room that guests of all ages will love. Plus, there is a private pool, a spa, a shaded patio with an alfresco dining set-up, sun loungers, and more. Inside, the villa has a luxe and trendy decor in the living, dining and kitchen areas. Nine gorgeous bedrooms and five contemporary bathrooms are also available in the villa. Disney and Universal theme parks are just a few minutes’ drive away.

Kissimmee, Florida, United States
42 reviews  
Entire villa 14 Beds 9 Bedrooms 5 Bathrooms
Top guest reviews
Host:
amazing home and very kid friendly
the host was awesome and my family will definitely be returning back
Amenities & Room:
there were marks up the walls the tiles in the bathroom weren’t completely clean
Read more reviews

8. Unforgettable vacation home near Disney World (from USD 232)

Highlights Luxury Family Friendly Work Travel

Best for: Families with kids, luxury travelers, group stays

A modern and stylish house within 4.8 miles (7.7 km) of Disney World, 11.5 miles (18.5 km) of Universal, 7.8 miles (12.5 km) from Sea World and within an easy drive from other major attractions. You have a kitchen with everything you need to cook your meals, Wifi, cable TV, laundry facilities, a laptop-friendly workspace, and access to the clubhouse of the resort. And, you get to enjoy two luxurious resort pools one of which comes with a lazy river. Stay here for a comfortable and fun holiday.

Kissimmee, Florida, United States
180 reviews  
Entire house 8 Beds 6 Bedrooms 5 Bathrooms
Top guest reviews
Host:
adriana was a great host
she was very responsive and accommodating
adriana is a great host
adriana’s is an amazing host
very good house and great host
Location:
the location was excellent and very convenient
also loved the location
great location beautiful house in gated community
great community for family vacationing shopping center really close by
the location is excellent to all the florida attractions
Cleanliness:
everything was clean and felt extremely sanitary
great place very clean and spacious
the house is beautiful clean and very spacious
it’s was super clean and homey
very nice and clean place modern and stylish
Amenities & Room:
wifi in the house is great
we had comfortable beds and great amenities
pools were great and everyone had a great time
the pool was terrific and private
the kids loved both the private pool and community pool with lazy river and water slides
Read more reviews

9. Stylish townhome with amazing amenities (from USD 307)

Highlights Luxury Family Friendly

Best for: Group stays, luxury travelers, families with kids

For a family holiday in Florida, book this amazing townhome in Bela Vida Resort that is just minutes away from Disney theme parks. Well-appointed and stylish, this home has a stunning interior done up in white, gray, beige and brown. An open-plan living and dining area is located next to a contemporary kitchen. Four luxurious bedrooms, three elegant bathrooms, and a game room complete the interior of the house with amazing amenities. You will also have access to a screened private pool, spa and patio area.

Kissimmee, Florida, United States
62 reviews   Wifi Available
Entire residential home 5 Beds 8 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 8

Top guest reviews
Host:
host is excellent communication was on point with any concerns
Location:
amazing house amazing location just all around amazing
we had a wonderful stay at this location
the home is also located at a very great location
will definitely be booking this place for future trips
home highly recommended very well located everything perfect
Cleanliness:
house was clean and good
the dishwasher is not working well so we had to clean the dishes by hand
great house really clean really quite neighborhood had a great time
be sure to not forget to bring cleaning stuff also
the house looks good and is clean but didn't make for a good relaxing vacation spot
Amenities & Room:
great interior and fun for the kids with an air hockey and billiard table
nice to have a comfortable place closed off from the mayhem of the tourist areas
the game room in the garage was perfect for rainy florida days
Read more reviews

10. Centrally located six-bedroom holiday villa

vrbo
Source: vrbo
Highlights Family Friendly Beach Access

Best for: Reunions, families with kids

This holiday home, located in Aviana Resort, is within a 20 minutes’ drive from Disney World and close to all other major tourist spots in Orlando. The spacious six-bedroom home comes with all the amenities needed for a comfortable stay. You get to enjoy Aviana Resort facilities as well: a stylish clubhouse, a picnic area, a sand volleyball court, beach access, and a children’s playground. There is also a huge resort-style pool with screens for privacy. You can avail pool heat at an additional cost.

24 reviews  
House 12 Guests 6 Bedrooms 5 Bathrooms

11. Comfortable three-bedroom house with a pool

Highlights Nature Retreat Family Friendly Budget Friendly

Best for: Nature lovers, group stays, families

Stay in this luxurious three-bedroom villa with a large family room that opens into a patio with a pool, a lounge room, dining room, and a well-equipped kitchen with a breakfast bar. Relax in the en-suite master bedroom that comes with a hot tub. The beautiful house pool, screened for privacy and equipped with loungers, a table, and chairs, is perfect for some family fun. There are ample parking spaces and a sprawling lawn that opens into a wooded area.

2701 shortleaf court
villa 6 Guests 3 Bedrooms 3 Bathrooms

12. Great vacation home near Disney World

homeaway
Source: homeaway
Highlights Family Friendly Budget Friendly

Best for: Families with kids, group stays

You are going to love this four-bedroom home on Indian Ridge within a few minutes drive from Disney World. As the house is professionally managed, you’ll have 24 hours guest service. There are all the necessities here, like a fully equipped kitchen, a game room, laundry facilities, parking, air conditioning, and much more. In addition, the house has a beautiful private pool where you can relax and have fun.

1539 Indian Oaks Trail
2 reviews  
House 8 Guests 4 Bedrooms 2 Bathrooms

13. Spacious home away from home

Highlights Family Friendly Budget Friendly Convenient Location Wellness

Best for: Group stays, families

If you’re looking for Kissimmee vacation home rentals with a private pool and a convenient location, then this property might interest you. This large three-bedroom home in Kissimmee is just an eight minutes’ drive from the Walt Disney World Resort area. The air-conditioned house offers all the necessary amenities. There are comfortable hardwood-floor living, dining, and kitchen spaces. All the bedrooms have flat-screen televisions and huge walk-in closets where you can store all the new clothes you buy at the Florida malls. After a day out, you can relax in the fully fenced garden area with a solar-heated pool and spa. There are lounge chairs by the glistening pool where you can stretch out and get a glorious tan.

39 reviews  
bungalow 6 Guests 3 Bedrooms 2 Bathrooms
Top guest reviews
Host:
Warm and welcoming felt at home straight away
We had a small issue with the stove during our stay and he sent an electrician out that same day to look into it
Pool is cleaned and maintained by a professional company once a week Mike is an awesome person to work with with any questions or concerns that you might have
it was replaced with a brand new ceramic top stove within a week The Hunter family who take care of the home are simply the best
This beautiful home was very comfortable and enjoyable for our family
Location:
location is brill queit area but near to amenities
Great location Quiet neighbourhood and easy access to all amenities and attractions Maintained and spacious
Third visit to this villa just booked the 4th visit great location to the Disney parks
No problems Loved it all week
that is an indication of the popularity of this property
Cleanliness:
It's lovely clean and spacious with a great pool
we were so pleasantly surprised at how spacious and inviting the home looked
Amenities & Room:
Everything you could possibly need provided The pool was larger than we expected and lovely and warm
The house is very comfortable with a fantastic pool kitchen equipped with everything you may need during your stay luxurious beds wifi and 1000s of TV channels
Lovely villa well furnished fantastic pool plenty of poolside furniture everything as I expected it to be Will be back
The villa is so comfortable you instantly feel at home
Very relaxing time with many hours spent by the pool couldn't have asked for anything better
Read more reviews

14. Cozy pet-friendly waterfront home

Highlights Nature Retreat Family Friendly

Best for: Nature lovers, families with kids, group stays

This clean and comfortable house can accommodate up to seven guests. You can drive to Disney World within 15 minutes, Seaworld within 20 minutes, and Legoland within 40 minutes. There are all the necessary amenities to make your stay comfortable: two lounge areas, a large fully-equipped kitchen with a dining area, outdoor dining on the lanai, an outdoor grill, games room, and free Wifi. What makes it one of the most beautiful Kissimmee home rentals with a private pool is the south-facing, private, screened pool and hot tub overlooking a scenic pond.

94 reviews   Wifi Available
House 7 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 7
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Host:
Marion was also great about responding quickly to any questions
We all four loved the pool especially our girls
There is an elongated wetland / pond about 100' away with an abundance of tweety birds and waterfowl all around
My kids really loved the good sized pool
it was a wonderful experience and the owner was always available if I need any questions answered Thank you again
Location:
Regardless of the supplies issue
The neighborhood was quiet and close to Disney World
The location was easy to find and not too far from restaurants and fun in Orlando Florida
Neighbours were wonderful Not far from Walmart
This house is centrally located in a quiet neighbourhood
Cleanliness:
It was clean and nicely located
The house was clean with anything you can need Pool clean and comfortable overall great place
however the beds were both very comfortable
Well designed clean house in a quiet neighborhood with plenty of space in most rooms
and I mean tiny) bar of soap in both baths
Amenities & Room:
There was plenty of space
Each of the 2 baths only had one partial roll of toilet paper that ran out quickly No paper towels in kitchen
The weather was kinda touch n go
We enjoyed playing on the pool table inside the garage / recreation room in the evenings
The kitchen and living spaces are enormous and more than enough for most families
Read more reviews

15. Vista Bay Villa

Highlights Family Friendly Convenient Location

Best for: Families with kids and infants, group stays

Vista Bay Villa is an incredible vacation rental if you’re looking for a place to stay with an outdoor pool. It also offers a pool heater that you can use for 20 USD a day. Inside this three-bedroom accommodation, you can use its TV and WiFi for entertainment. You can also catch a breath of fresh air on the property’s patio.

Within the area, you can check out nearby recreational spots such as the Kissimmee Sports Arena & Rodeo and Kissimmee Golf Club. For family fun, you can also try skating with your loved ones at Skate Reflections located 1.4 miles (2.25 kilometers) away from the villa.

Kissimmee, Florida, United States
PRIVATE VACATION HOME 6 Guests 3 Bedrooms 2 Bathrooms

Top guest reviews
Host:
owners were very nice and answered promptly with any concerns we had thank you
owners were super very easy to get ahold of and very quick response wonderful outdoor area too
Location:
it’s also close to many attractions
perfect location for a week of volunteering at give kids the world village
everything was very comfortable and cozy central location able to deliver groceries and cook there to save
good location close to the parks and a very nice quiet community
Cleanliness:
the house was very clean and comfortable
house was nice tile everywhere so it's easy to clean but a little echoey
Read more reviews

16. Elegant rental with a private pool

Highlights Pet Friendly Family Friendly Luxury

Best for: Pet parents, families with kids and infants, group stays

This four-bedroom vacation rental invites its guests over to its serene swimming pool. It also offers a central air-conditioning unit, washer, dryer, an indoor tub, linens, and toiletries. For entertainment, you can also use its 55-inch TV and WiFi. You can also bring your car during your stay and park it in the available garage of the unit.

If you want to explore the area, you can visit Disney Springs and find good deals from the retail shops. If you’re with kids, you can also drop by Kissimmee Go-Karts which is only 1.6 miles (2.57 kilometers) away.

Kissimmee, Florida, United States
PRIVATE VACATION HOME 8 Guests 5 Bedrooms 4 Bathrooms

Top guest reviews
Location:
excellent property and good location
the location of the townhouse is perfect for orlando
perfect for big group to be in one place rather than booking a hotel
Cleanliness:
everything was clean and the kitchen had all the essentials to cook
everything was clean and very close to shopping and restaurants
very nice place safe clean quiet close to the market disney parks
Amenities & Room:
nice pool and amenities
overall this is a nice property with cool air conditioning and in a safe quiet part of town
Read more reviews

17. Fully air-conditioned home with lakeside setting

Highlights Family Friendly Waterfront Budget Friendly

Best for: Families with kids, nature lovers, group stays

The remarkable lakeside scenery of this fully air-conditioned home is perfect for guests looking to vacation in a peaceful urban retreat. This relaxing property in Eagle Pointe South allows you to enjoy an inviting outdoor pool with views of a private lake brimming with wildlife and technicolor sunsets. You can request the pool to be heated for an additional nightly fee of 15 USD.

The tranquility of the lake can similarly be enjoyed from the living room, which comes with a 42-inch flat-screen TV. If you’re all about entertainment that appeals to both kids and adults, the property’s game room with WiFi and pool and ping pong table will be a hit. Don’t forget to rustle up some snacks in the fully-equipped kitchen before game time.

Kissimmee, Florida, United States
PRIVATE VACATION HOME 8 Guests 4 Bedrooms 2 Bathrooms

Top guest reviews
Host:
the owners are easy to work with
Location:
close to places of attraction and places to shop
Cleanliness:
clean house with all amenities functioning
Read more reviews

18. Lakeview paradise near Walt Disney World

Highlights Pet Friendly Family Friendly Waterfront

Best for: Pet parents, families, group stays

By staying in this rental, you can take relaxing dips in the private pool and enjoy views of the beautiful lake at the same time. The pool area is south-facing and can be heated at an additional fee. When you’re not swimming, you can also explore some places of interest nearby, including Walt Disney World, restaurants, and local shops.

Featuring four bedrooms and two full bathrooms, this abode is perfect for a total of eight guests. It also offers a fully equipped kitchen and a bright living room with a TV. The place is equipped with heating and air conditioning, not to mention speedy WiFi.

Liberty Village,, Florida, United States
PRIVATE VACATION HOME 8 Guests 4 Bedrooms 2 Bathrooms

Top guest reviews
Host:
most importantly contact info should be up to date and property owner respond
Location:
it was a quiet neighborhood but close to shopping restaurants & entertainment
Cleanliness:
the house was very clean and spacious
walked in to clean the property and lifted up the sheets and there were bugs
Amenities & Room:
the pool was a ton of fun and there's a bbq grill so you have pretty much everything
house was nice except for the sugar ants that were in the kitchen and got into our food
Read more reviews

19. Spacious accommodation with a covered pool area

Highlights Family Friendly Waterfront Budget Friendly

Best for: Nature lovers, reunions, families

Looking for a spacious rental to accommodate your large party? This 4-bedroom, 3-bathroom townhome has ample living space to take in a total of 13 guests. It also offers a private pool to complete your getaway. The pool area is covered so you can enjoy private swimming during your stay. It also features seating and a gas grill for a great hangout outdoors. Other amenities in the rental include heating, air conditioning, WiFi, and a cable TV.

When you’re not cooling off in the pool, you can also explore some places of interest nearby. These include Kissimmee Lakefront Park and Brinson Park, both located just within 1 mi (1.6 km) of the property.

18 reviews   Wifi Available
townhome 12 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 12
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Location:
we had the perfect location and will be back
we had tons of fun great location
it was close to the express way with an easy quick drive to the parks and outlet malls
the pool in the community is great and it's close to many things
we were super close to attractions and had so many options for food that we never cooked
Cleanliness:
everything was clean and looked brand new
rooms were beautifully decorated comfortable and clean
Amenities & Room:
the only suggestion we have is to have a welcome book to communicate club info wifi password etc
was great stay buy pool didn't have light and was dark
the pool was private and the perfect size for our small kids
Read more reviews

20. Lovely home with access to clubhouse amenities

Highlights Luxury Family Friendly Waterfront

Best for: Outdoor enthusiasts, luxury travelers, families with kids, group stays

Staying in this lovely vacation rental means you can enjoy access to the clubhouse’s many amenities, including water slides, kayaks, a beach volley court, a tiki bar, and a lazy river. Its convenient location also allows guests to easily reach areas for shopping, dining, and entertainment in the city. If you want to enjoy yourself without leaving the premises, however, you can just soak and take refreshing dips in the rental’s private pool.

The rental can comfortably accommodate a total of 11 guests. It offers 5 bedrooms, 4 bathrooms, and a fully equipped kitchen. For comfort, air conditioning and heating are provided.

21 reviews   Wifi Available
townhome 11 Guests 5 Bedrooms 4 Bathrooms

Accommodates: 11
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Location:
easy check in great location
the location was close to restaurants attractions and local stores
loved the location and property was very clean
having previously rented larger properties in the area and having awesome experiences this place was mediocre at best
Cleanliness:
everything was clean and modern
the house was nice and clean
the home was clean and updated/modern
the property was well decorated generally clean and close to disney
Amenities & Room:
community pools lazy river and hot tub were great
would recommend heating the pool
Read more reviews

21. Spacious rental with high-speed internet

Highlights Family Friendly Budget Friendly

Best for: Families with kids, groups

At this spacious rental, you can plunge into the private pool and work on your swimming strokes. Else, you can pay additional charges to have it heated and spend hours soaking in it to rid your body of all the exhaustion. However, if you don’t want to pay extra, you can simply draw up a bath in the soaking tub in one of the bathrooms.

After a full day of fun, you can retire to the comfy bedrooms prepared to ensure restful sleep. One of them is specially prepared for children, so the young guests will be happy also.

Kisssimmee, Florida, United States
villa 10 Guests 4 Bedrooms 3 Bathrooms

Top guest reviews
Host:
i contacted the owner and he said the manager will take care of it
Location:
great location everything we need as a family
good location for any direction of travel
was a real nice house in a pretty nice location in kissimmee
the atmosphere is inviting and it is conveniently located to the shops and parks
Cleanliness:
the house is spacious clean and comfortable and well equipped
Amenities & Room:
the pictures online showed there were four very nice looking lounge chairs around the pool
Read more reviews

22. Carousel Villa

Highlights Family Friendly Luxury

Best for: Group stays, families, luxury travelers

Carousel Villa is a luxury accommodation located in a gated community at Kissimmee’s Cumbrian Lakes. The house is equipped with all the comforts of home. You can prepare a full meal in the kitchen and relish it in the dining area. Once you’re done, you can head to the private pool and refresh yourselves by swimming a few lengths. The pool can be heated for an additional charge, so you can consider dipping into it to relax your muscles as well.

After a fun swimming session, you can enjoy some indoor entertainment as there is a games room, where you will find a pool table, foosball table as well as air hockey.

Kissimmee, Florida, United States
villa 8 Guests 4 Bedrooms 3 Bathrooms

Top guest reviews
Location:
the location was close to everything and they enjoyed the gameroom
Cleanliness:
clean good beds well stocked kitchen
this house was beautiful clean and a perfect find for our family
Amenities & Room:
the kitchen was supplied very well and the amenities were all as stated in the vrbo website
the heated pool was awesome would rent this house again
great stay with a beautiful pool area
Read more reviews

23. Beautiful fully furnished home with private pool

Highlights Family Friendly Good Neighborhood Convenient Location

Best for: Families with kids and infants, reunions

Located in a prestigious gated community, this vacation rental offers you everything you will need to make your family getaway a lot more memorable. It’s only 30 minutes from Orlando International Airport and a few minutes from Orlando and Kissimmee’s top restaurants, shops, museums, and of course, popular theme parks.

More than just the premier location, the property itself is something to be excited about. It consists of six bedrooms that can sleep up to 12 guests, 4 full baths and a half bath, and a cozy living room with a nice sofa set and a large TV. Guests also have access to a 9-seater dining area, a fully equipped kitchen, and a private sun deck with a dining set, lounge seats, and a swimming pool, which can be heated for an extra fee.

Amenities also include WiFi, a pool table, darts, and foosball for extra indoor entertainment.

64 reviews   Wifi Available
House 12 Guests 6 Bedrooms 5 Bathrooms

Accommodates: 12
Minimum Nights: 5
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Host:
the property manager was friendly and accommodating when we had questions
Location:
the community is close to lots of shopping and entertainment and is very peaceful and quiet
upon arrival the location was very lovely and home was clean
Cleanliness:
cleanliness was great
the pool was pleasant clean and warm
the property is cozy and clean
the vacation home was a clean convenient and comfortable getaway for us
Amenities & Room:
pool was great we paid extra to have it heated which was totally worth it
pool table and foozball table were added fun
Read more reviews

24. Spacious rental in Country Creek Estates

Highlights Family Friendly Nature Retreat Waterfront

Best for: Families with kids, group stays, nature lovers

Here’s a beautiful rental located in Country Creek Estates. This home is equipped with all the amenities, including air hockey and a pool table for your indoor entertainment.

Alternatively, you can head to the pool deck and jump into the private pool to splash around a bit. A few pool toys and inflatables have also been made available to add to the enjoyment. Those who don’t want to step into the water can sunbathe as the deck receives sunshine all through the day. The transparent wall around the pool makes it possible to enjoy the serene lake views.

One of the bedrooms at the rental opens out into the pool deck. If you are intending to allocate this bedroom to your kids and are afraid that they may enter the pool unsupervised, do not fret as alarms are fitted into the deck door to detect any such activity.

98 reviews   Wifi Available
villa 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 5
Refund Policy :

Top guest reviews
Host:
owners were very nice doing business with and even had toys available for the kids
Location:
the location was perfect
close to a lot fun attractions
great location and beautiful home for any family
Cleanliness:
everything was very clean and comfortable
the property was clean and had an excellent pool
the house was very clean pool is very nice close to walmart spacious safe area
loved the pool and it was very spacious
Amenities & Room:
and the pool was delightfully heated to our amaze
by far the best feature for us was the heated pool
beds were too firm for us but mattresses are pretty subjective so can't really complain about that
Read more reviews

25. Disney-themed townhome in a resort

Highlights Family Friendly Unique Theme

Best for: Families with kids, group stays

Your kids will absolutely love staying at this Disney-themed townhome in Bella Vida Resort. This family and pet-friendly home offers luxurious living with a touch of Disney magic in its decor. Relax in the open-plan living, dining and kitchen area that looks out to the private pool. Four themed bedrooms and three spacious bathrooms are available for the use of up to 10 guests. The pool area has a barbecue grill and sun loungers too. Disney parks are at a 15-minute driving distance from this townhome.

7 reviews   Wifi Available
townhome 10 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 10
Minimum Nights: 1
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Cleanliness:
upon check in the house was clean and smelled amazing
Read more reviews

26. Lovely vacation home with waterfront views

Highlights Family Friendly Wheelchair Friendly Waterfront

Best for: People with access needs, families with kids, nature lovers, group stays

Entertainment of all sorts is abundant and within easy reach from this vacation home. Theme parks and attractions in central Florida are only a quick drive from this property while several family restaurants and a supermarket can be effortlessly accessed on foot.

When you’re not out seeking thrills, you can simply opt for a soak in the rental’s large screened-in pool. The area enjoys a waterfront view and comes with tables and chairs in the shade so you and your crew feel extra relaxed. This wheelchair-accessible rental has choices for fun that engage both kids and adults, including a pool and foosball table, 55-inch flat-screen TV, and WiFi. Guests must note that only two cars are allowed in the parking space and stays for at least five nights are accepted.

Kissimmee, Florida, United States
Wheelchair accessible Visual Aid: Braille
villa 8 Guests 4 Bedrooms 2 Bathrooms

Top guest reviews
Host:
host was very responsive to inquiries
Location:
close proximity to eats and entertainment and the parks
excellent space very good location attentive hosts
great location clean and quiet neighborhood
mainly residential i think very quiet with properties kept in good condition
Cleanliness:
it was very clean
the beds were comfy with very clean bedding
the house was amazing super clean
the house was great everything was comfortable and clean
we loved the home very pleasant stay and very clean house
Amenities & Room:
the pool side furniture was of good quality and the pool was very clean
beautiful home very nice having private pool is even better
the games room was a huge hit with my youngest son
the beds were extremely comfortable and the neighborhood was very quiet
my family really appreciated the little details the house offered as we are avid disney fans
Read more reviews

27. Lightwater Villa

Highlights Family Friendly Luxury Waterfront

Best for: Nature lovers, families with kids and infants, group stays

Perfect for holiday getaways, Lightwater Villa is an accommodation located inside the Bella Vida Resort. With an area of 2,000 square feet (185.81 square meters), this spacious vacation rental features a relaxing outdoor pool where you can swim and unwind. For only 35 USD per day, you can also use its pool heater.

A gated parking space is available for use on this property. Inside, the villa offers a TV, WiFi, a washer, a dryer, a refrigerator, an air-conditioning unit, and plush linens. You can also work wonders with your recipes in its fully equipped kitchen.

Kissimmee, Florida, United States
villa 10 Guests 4 Bedrooms 3 Bathrooms

Top guest reviews
Host:
the property manager is also very responsive
thank you to the owner's for allowing us to stay at your home
the management company was responsive before and during our stay
Location:
close to all attractions and restaurants and grocery stores
what a find a beautiful house with a pool in a great location for everything
Cleanliness:
the house is very clean and well maintained
we loved this house it was clean and they made the check in very easy
Amenities & Room:
only problems was that the kids didn’t get to enjoy the hot tub or warm pool
Read more reviews

28. Charming studio with private pool

Highlights Couple Travel Budget Friendly Convenient Location

Best for: Couples, solo travelers

This charming studio has all the amenities for a comfortable stay. You’ll find everything you need such as a washer, a dryer, a refrigerator, a fully-equipped kitchen, linens, a flat-screen TV, and WiFi. If you’re bringing a car, you can also use its free parking space.

This property is also accessible to some points of interest in town. Situated 1.7 miles (2.74 kilometers) from the rental, you can visit Osceola Performing Arts Center if you’re into theatre. Brinson Park is another nearby spot that you may check out if you want to walk around or go fishing.

Kissimmee, Florida, United States
Apartment 2 Guests 1 Bedroom 1 Bathroom

Top guest reviews
Host:
hosts are awesome and informative
nazim was a wonderful host
the courtesy and helpfulness of the property owner were top notch
i enjoyed the visit and the place was nice but not private because owner lives on property too
Location:
huge walk in shower
Cleanliness:
communication was amazing and the facility was clean
owners are wonderful very easy check in very clean property
Read more reviews

29. Stunning house with lake views

Highlights Nature Retreat Family Friendly Waterfront

Best for: Nature lovers, families with kids and infants, group stays

Located next to Eagle Point Lake, this gorgeous vacation home boasts a lanai-shaped private pool covered by a glass dome. It receives sun all day, making it a perfect place for enjoying water activities inside your home. The pool deck is furnished with six pool loungers and dining furniture where you can grab quick bites to pair with your favorite mix of cocktails. The pool deck leads to a lounging area with recliners and a TV for ultimate relaxation.

The home also has a fully furnished kitchen for your culinary activities. You can cook delicious meals and eat them at the large dining table in the aesthetically designed interiors or go for a picnic by the lake. There are pool towels available that can also be used after a refreshing swim in the lake.

Kissimmee, Florida, United States
PRIVATE VACATION HOME 8 Guests 4 Bedrooms 2 Bathrooms

Top guest reviews
Location:
the pool was great and it is close to all the major attractions
Cleanliness:
house was clean modern and very spacious
accommodated everyone pool was clean kitchen big
Amenities & Room:
my family of 4 spent an amazing week at this house the pool and view was so perfect
beautiful to sit by the pool and look out over the lake
Read more reviews

30. Gorgeous villa with a games room

Highlights Family Friendly Waterfront Wheelchair Friendly

Best for: Families with kids and infants, group stays

This spectacular villa on Eagle Point Lake is perfect for a family vacation. It is equipped with a fully furnished kitchen and a cozy living area. The games room here features a football table, an air hockey table, and a pool table where you can challenge your loved ones for a friendly game.

But the best part about this property is its luxurious pool area overlooking a beautiful lake. The pool deck is covered in a glass dome and features six chairs, a dining table for al fresco luncheons, two sun loungers with a parasol, and a side table. Unwind with an invigorating swim in the heated pool, and then relax with a cocktail on the sun loungers. Alternatively, you can use the hot tub for a warm soak and a therapeutic experience.

Kissimmee, Florida, United States
Wheelchair accessible Visual Aid: Braille
villa 6 Guests 3 Bedrooms 2 Bathrooms

Top guest reviews
Host:
the owner and property manager were very responsive to any questions we had during our stay
Location:
a beautiful house in a great location
great area and a short drive to all the parks
Cleanliness:
the villa is very clean and comfortable
overall the place was clean and the pool and hot tub were great
Amenities & Room:
a heated pool and heated tub made all the difference for a relaxing evening
had fun in the game room and relaxed in the pool
Read more reviews

31. Pleasant home with a pet-friendly policy

Highlights Pet Friendly Family Friendly Waterfront

Best for: Pet parents, families, group stays

This vacation home welcomes you and your furry friends for a relaxing stay in its lavish interiors. It is equipped with a fully furnished kitchen for your culinary activities and a comfortable living room for you to unwind.

The lounging area leads to a screened private pool that overlooks a stunning lake. After a refreshing dip in the pool waters, enjoy a cocktail while relaxing on a sun lounger or take your loved ones for a picnic by the lake. And for an additional price, you can even enjoy a warm soak in the heated pool at night.

Kissimmee, Florida, United States
villa 6 Guests 3 Bedrooms 2 Bathrooms

Top guest reviews
Host:
owner very responsive to questions and answered quickly accommodation was good standard good location for parks
Location:
it was great location for the parks
getting to disney from this location was very easy
it was very close to disney and would definitely rent out this property again highly recommend
Cleanliness:
clean peaceful and beautiful house for vacation
loved the property the house was very clean and homey
Amenities & Room:
the pool was great and had an awesome view of the lake
we requested the pool heated and it was very pleasant
Read more reviews

32. Lakeside home with a private pool

Highlights Family Friendly Budget Friendly Waterfront

Best for: Nature lovers, families with kids and infants, group stays

This stunning property boasts an intricately designed living room furnished with plush sofas and a well-equipped kitchen for your cooking adventures. Book a stay here and enjoy the tranquil views of the lake, or unwind with an invigorating swim in the pool.

The poolside deck features a dining table and chairs with a parasol to enjoy quick bites under the shade. There are sun loungers for you to bask in the warmth of the sun, and, for an additional cost, you can even have the pool heated.

Kissimmee, Florida, United States
Wheelchair accessible Visual Aid: Braille
villa 8 Guests 3 Bedrooms 2 Bathrooms

Top guest reviews
Host:
the owners and company were very helpful and responded quickly
Location:
close to everything and in a good neighborhood
we loved this place
this house all around was a fantastic place to stay
Cleanliness:
property was clean and perfect for our family
Read more reviews

33. Spacious accommodation with lake views

Highlights Golf Course Access Pet Friendly Family Friendly Waterfront

Best for: Golf enthusiasts, pet parents, families, group stays

Enjoy the best of both worlds in this spacious accommodation that sits in a peaceful location yet is only a few minutes away from Walt Disney World and a wide range of golf courses. The property is in the peaceful community of Liberty Village and boasts a screened pool overlooking a lake. This private pool, which comes with heating at an additional cost, has a safety fence and lights for night swimming. Shaded furniture, padded armchairs, and reclining sun loungers are also provided to enhance the outdoor experience.

This rental is further appointed with full air-conditioning, a games room with a pool table and basketball, cable TV, and free WiFi for a highly amusing stay. Parking is a major plus as well.

Kissimmee, Florida, United States
villa 8 Guests 4 Bedrooms 2 Bathrooms

Top guest reviews
Host:
the owner was great responds almost immediately & is very kind
check in was a breeze and the information sent by the owners very helpful
Location:
very close to all attractions you could possibly want to visit
Cleanliness:
very spacious exceptionally clean & well maintained
Amenities & Room:
we had a great and comfortable stay
the house was comfortable and well maintained
Read more reviews

34. Luxury villa ideal for vacationing large families

Highlights Family Friendly Golf Course Access Work Travel

Best for: Families with kids and infants, golf enthusiasts, group stays

Located in the ideal community of Indian Point, this luxury villa is a huge home ready to accommodate up to two families vacationing together. The best way to kick off any getaway here is to make a splash in the backyard’s sparkling pool. There’s also a spa and decking area with ample loungers and a grill in this outdoor space, making it more enjoyable for all family members. Pool and spa heating can be arranged and comes at separate fees.

The rental will keep your indoor stays amusing with the appointed cable HDTV and free high-speed WiFi. Any of the bedrooms with comfortable beds are sweet havens for restful slumbers while the well-equipped kitchen is guaranteed chef-ready.

Kissimmee, Florida, United States
villa 10 Guests 5 Bedrooms 3 Bathrooms

Top guest reviews
Location:
it’s in a nice quiet area and it’s close to a walmart for those much needed essentials
Cleanliness:
overall our stay was good the property inside was clean
Amenities & Room:
it also has plenty of space and the pool and spa area was great
pots and pans selection was excellent pillows and beds could use some updating but were serviceable
Read more reviews

35. Pet-friendly and cheerful home

Highlights Family Friendly Good Neighborhood

Best for: Group stays, families with kids

Set in a quiet and safe neighborhood in Eagle Pointe South, this cheerful home is sure to capture your attention with its outdoor swimming pool. Its fenced backyard showcases a screened-in pool with ample alfresco space to unwind. You can recline in any of the beach chairs, pop open the gas grill to cook some barbecue, or cool off by the fire pit in this outdoor space.

Meanwhile, the property’s interior is a modern space that features a living room with an electric fireplace and smart TV as well as a full kitchen for all your meal plans. WiFi is on-hand in this rental to keep you online.

Kissimmee, Florida, United States
PRIVATE VACATION HOME 5 Guests 2 Bedrooms 1 Bathroom

Top guest reviews
Host:
great communication with owner and manager
Cleanliness:
no issues love the place clean spacious
Read more reviews

36. Cozy bungalow filled with great amenities

Highlights Family Friendly Nature Retreat Long Term Stay

Best for: Outdoor enthusiasts, families with kids and infants, group stays

Be invigorated with the whole family in this cozy bungalow that struts a screened and enclosed pool. The open-air space extends to a covered lanai and a large deck capturing great views of a conservation wildlife area. Its surroundings are fitted with chaise loungers, an outside shower, and a towel rack for a convenient time under the sun.

Online and offline options for enjoyment are abundant, with a 55-inch (139.70 centimeter) smart HDTV, speedy WIFI, stereo system, books, games, and pool toys made available in the unit. Comfort and convenience are also ensured in other areas such as the kitchen complete with essential appliances and bedrooms with their own cable TVs. Be aware that this home only accepts bookings for at least five days.

Kissimmee, Florida, United States
PRIVATE VACATION HOME 10 Guests 4 Bedrooms 2 Bathrooms

Top guest reviews
Host:
the owner is very easy to communicate with via email
very professional and kind
wal-mart is close by in case you need anything and the owner was fantastic to work with
Location:
great pool and location
the neighborhood is peaceful and close to grocery stores and attractions
it was a nice quiet safe neighborhood and not to far from attractions
other than that it was perfect for our disney trip since it was close to the parks
Cleanliness:
house was big and clean
this property was well maintained clean and nicely furnished
the home is clean and had most everything we needed for our stay
Read more reviews

37. Charming paradise in Central Florida

Highlights Family Friendly Work Travel Convenient Location

Best for: Families with kids, group stays

Set in Central Florida, this charming paradise is spacious enough to accommodate a total of 10 guests. It offers 4 bedrooms, 2 bathrooms, a family room, and a fully furnished kitchen. The highlight of this rental is the large, in-ground pool placed in its beautiful backyard. It is surrounded by lounge chairs and a fire pit so you can have a spot where you can relax during your stay. Other amenities in the rental also include Wi-Fi, air conditioning, and a smart TV.

Some places of interest nearby are Disney World Parks, Universal parks, Sea World, and Gator World.

Kissimmee, Florida, United States
PRIVATE VACATION HOME 8 Guests 4 Bedrooms 2 Bathrooms

Top guest reviews
Host:
the host was responsive when needed
wonderful stay the home is updated and has a lot of room to host a large family or two
home is beautiful and very clean the host were amazing and clear with instructions for my arrival and departure
Location:
the location was great for the local attractions
i would definitely recommend this location
the location is perfectly nestled in a quiet clean subdivision stores and restaurants are conveniently close
the neighborhood was very nice and quiet
clean house and close to disney world and universal studios
Cleanliness:
very clean and had everything we needed for a relaxing family vacation
Amenities & Room:
we appreciated the good wifi connection and smart tvs around the house as well
the house even had cute bottles of shampoo conditioner and body wash in each bathroom
we had plenty of room to spread out and the kids enjoyed the pool
the private pool privacy fence and detached guest house were perfect for our family
Read more reviews

38. Comfortable modern home in a great location

Highlights Family Friendly Waterfront View

Best for: Group stays, families with kids and infants

Planning to treat your family to a wonderful vacation in Kissimmee? Here’s a great home base to make your vacation more memorable. It is nicely located in a quiet residential community with direct access to a scenic lake. It’s also quite close to some of Florida’s top attractions including several theme parks and state parks. Disney World, Universal Studios, SeaWorld, Cape Canaveral, and the beaches, for instance, are less than an hour’s drive away.

The beautiful property can certainly make your stay as relaxing as possible. It is fully furnished and has enough space to accommodate up to nine people. The fully equipped modern kitchen will ensure food preparation is as easy as pie.

Upstairs you’ll find a den with a sofa bed, a TV, PS2 and games, a stereo, and a VCR for indoor entertainment. The place also features a pool at the back overlooking the scenic lake. You can request for it to be heated for a fee.

Kissimmee, Florida, United States
PRIVATE VACATION HOME 9 Guests 4 Bedrooms 2 Bathrooms

Top guest reviews
Location:
the neighborhood where the house was located is very quiet and peaceful
this was the perfect place to stay for an amazing time away
house was very nice in a quiet neighborhood
Cleanliness:
the bathrooms could use some upgrades but overall was very clean and accommodated our family well
the pool area was very nice and clean
clean lots of space plenty of cookware in the kitchen pretty much everything you need
Amenities & Room:
we opted for the pool to be heated and the water was perfect
only suggestion would be a umbrella for pool as the pool area was mostly sunny
pool was great perfect size and well lit for swimming at night
Read more reviews

39. Waterfront home with pool and spa near Disney

Highlights Family Friendly Waterfront Golf Course Access

Best for: Nature lovers, families with kids and infants, golf enthusiasts, group stays

This kid-friendly home is your gateway to an amazing vacation in Kissimmee. Disney parks and other popular attractions are but a few minutes away. Shops, restaurants, grocery stores, and other establishments are nearby as well.

Its waterfront location is great if you just want to enjoy the beautiful and relaxing lake vista. For an additional fee, the pool and spa can be heated so that you and your fam can enjoy soaking your troubles away while enjoying the water views at night. It has four bedrooms to provide comfortable sleeping space for up to eight guests. Other amenities include free high-speed WiFi access, a game room with darts and a pool table, and a fully equipped kitchen with a nice breakfast bar.

Kissimmee, Florida, United States
Wheelchair accessible Visual Aid: Braille
PRIVATE VACATION HOME 8 Guests 4 Bedrooms 2 Bathrooms

Top guest reviews
Host:
helpful signs with instructions and directions for trash pool use laundry etc clearly displayed throughout the house
the owner bill is a pleasure to work with and responded quickly to any questions we had
great place to stay everything well maintained and owner easily accessible for questions
bill was so nice to work with very responsive especially when we needed him
also the neighbors were very friendly and helpful
Location:
the location is good
quiet location peaceful lake and backyard
great vacation close to a lot nice layout
was a great location for everything we had planned and needed to do
the neighborhood is welcoming and quiet
Cleanliness:
the house was extremely clean
it was clean with a variety of entertainment options
the pool and hot tub were so nice the rooms were nice and clean and very spacious
the home was clean and well appointed
the house was very clean and communication with the owner was excellent
Amenities & Room:
the furnishings were very comfortable and even had a plush throw on the couch
we enjoyed the pool spa and the furniture/beds were very comfortable
the living room and dining room were super nice
if we had more room to pack more stuff we definitely would have cooked more
the pool was warm the hot tub was nice and relaxing
Read more reviews

40. Gorgeous home with pool within Country Creek Estates

Highlights Pet Friendly Family Friendly Convenient Location

Best for: Pet parents, families with kids, group stays, nature lovers

Located within the beautiful and quiet community of Country Creek Estate, this beautiful home offers you the tranquility you’d want during your getaway. It’s also pretty close to many of the region’s top attractions including, of course, theme parks, outdoor recreational destinations, and more.

This vacation home is perfect for families and friends of up to eight people. It has three bedrooms, two baths, a living room, and a kitchen—all fully furnished and equipped with comfort and convenience in mind. It also boasts a large, private, and screened backyard with a pool—a great spot to just unwind and enjoy a great time with family and friends.

Kissimmee, Florida, United States
PRIVATE VACATION HOME 6 Guests 3 Bedrooms 2 Bathrooms

Top guest reviews
Host:
owners and management company were easy to deal with
thank you geoffery and karen for being such wonderful hosts
owners and managers checked in on us to see if everything was good
everyone was very friendly and helpful and provided all the necessary information
great communication with both the owners and property manager
Location:
loved the location house and pool
house was perfect location fabulous neighborhood perfect
but overall enjoyed the house location and the quiet
the location is absolutely perfect for short commutes to all disney parks
great house in a nice area close to activities if you want them of just relax at the house
Cleanliness:
clean property in a nice neigjborhood
the house was super clean
i also appreciated that it smelled fresh and was very tidy
the house was clean comfortable and fully stocked with everything we needed
great rental home this home met my high cleanliness standards
Amenities & Room:
we enjoyed the pool and nice outdoor furniture
loved the warm pool where you can relax and read
beautiful home with a pool
pool was great king bed was extremely comfortable i loved everything about it
the pool was nice provided our son with many hours of entertainment
Read more reviews

41. Luxurious vacation villa close to major attractions

Highlights Luxury Family Friendly Convenient Location

Best for: Reunions, families with kids and infants

Great for family getaways in Kissimmee, this villa offers you not just comfortable accommodation but easy access to some of the region’s major attractions. It’s situated in a beautiful gated community, which happens to be centrally located close to Disney World, Universal Studios, and SeaWorld as well. Several destinations for outdoor recreational activities are also just minutes away.

The luxurious villa offers a minimum stay of five nights. It is fully furnished to ensure comfort and convenience and has six bedrooms that can sleep up to twelve people. The kitchen is equipped with modern appliances for easy food preparation. There are also some indoor entertainment options to enjoy including foosball, air hockey, a gaming console, a huge 65-inch TV, and more.

The best part of the property is definitely the screened outdoor area with a pool and grilling facility, the perfect place to just relax and enjoy the sun.

Kissimmee, Florida, United States
PRIVATE VACATION HOME 12 Guests 6 Bedrooms 4 Bathrooms

Top guest reviews
Location:
there was plenty of room for everyone (8 adults) and it was close to everything
Cleanliness:
the house could use some updates and a deep clean
Amenities & Room:
beds were sooooo comfortable
Read more reviews

42. Fully furnished rental with lake views

Highlights Family Friendly Waterfront Budget Friendly

Best for: Families with kids, nature lovers, group stays

With a private pool that looks out to the larger lake in Eagle Pointe, this vacation rental is one of the best places to stay in Kissimmee. The pool deck also features outdoor seating so you can relax and watch beautiful sunsets across the waters.

The rental is suitable for a total of eight guests. It offers four bedrooms, all with TVs. There are also two bathrooms as well as a living room with comfy seating and an entertainment system. The kitchen is equipped and ready for home cooks. Other indoor features also include central air conditioning, WiFi, games, and books. If you have a car, you can park in the on-site garage which has ample space for up to two vehicles.

Kissimmee, Florida, United States
PRIVATE VACATION HOME 6 Guests 4 Bedrooms 2 Bathrooms

Top guest reviews
Host:
neil is a great host
Location:
close to all in central fl enjoyed our time here
we loved how close everything was
it’s really well located not too far from a walmart the outlets and disney world
the house was in a great central location for everything we needed
the house is in a great location easy access to disney property
Cleanliness:
everything clean and very organized
it was clean beautiful quite and in a great location
it was very nice clean and a very nice place for kids and adult
once there we loved how clean it was we really enjoyed staying there
home was clean in a nice neighborhood great location for things to do in and around orlando
Amenities & Room:
the view from the pool area is beautiful
the pool was amazing and worth the extra to have it heated
the space was perfect and the pool and lake were the highlight of our stay
kids enjoyed pool we enjoyed grilling on patio
it was a great place to stay with plenty of room for all of us
Read more reviews

43. Lakeside oasis best for families

Highlights Family Friendly Waterfront Work Travel

Best for: Nature lovers, families with kids and infants, group stays

Treat your family to an ultimate lakeside getaway in this vacation rental, which offers a heated pool overlooking the man-made lake. You can start your day with a breakfast in the screened-in pool area then spend the rest of the hours cooling off in the pool, playing games in the game room, or exploring the closest theme parks.

Orchid Place offers family-friendly amenities such as children’s books, toys, a travel crib, and a high chair, making it a perfect stay for you and your loved ones. The place also features two bedrooms, two full bathrooms, and a well-stocked kitchen. It has enough living space to accommodate a total of eight guests. Amenities such as air conditioning, WiFi, and smart TVs are also available.

Kissimmee, Florida, United States
PRIVATE VACATION HOME 8 Guests 3 Bedrooms 2 Bathrooms

Top guest reviews
Host:
the owner and caretaker were such a pleasure
the owners thought of every detail to make our stay comfortable
check-in was a breeze lois was a fantastic host providing all information needed
Location:
the house location was great
this home was perfectly tucked in a quiet cul-de-sac close to lots of shops and minutes from major freeways
great location for disney great pool clean home
orchid place is a beautiful home and a great neighborhood
Cleanliness:
clean convenient great location
very clean beautiful view
Amenities & Room:
we spent every day enjoying the pool and the views from the lanai
very nicely decorated house with wonderful pool and view
Read more reviews

44. Beautiful holiday home with a heated pool

Highlights Golf Course Access Family Friendly Waterfront

Best for: Nature lovers, golf enthusiasts, group stays, families

Enjoy the best of lakeside living when you stay in this beautiful holiday home. It boasts a sparkling pool set in a private, screened-in area overlooking the lake. If you prefer the pool to be heated, you can also arrange it with the host at an additional nightly fee.

The place is suitable for a total of six guests. It has three bedrooms, two full bathrooms, a laundry room, and an updated kitchen. This lakefront home features modern conveniences as well, including Wi-Fi and air conditioning. For entertainment, TVs are provided in the living room and master suite. You can also enjoy easy access to Disney resorts and theme parks found just within driving distance.

Kissimmee, Florida, United States
PRIVATE VACATION HOME 6 Guests 3 Bedrooms 2 Bathrooms

Top guest reviews
Location:
the neighborhood & gate staff always alert & friendly which is not often the case other places
Cleanliness:
very clean and inviting
well stocked and very clean
was happy to walk in and see how clean open and bright the home was
Amenities & Room:
please consider getting a new mattress for master bed
Read more reviews

45. Humble abode with lake views

Highlights Nature Retreat Family Friendly Waterfront

Best for: Nature lovers, families, group stays

From stunning lake views to modern amenities, this four-bedroom home offers you a relaxing getaway in Kissimmee. You can enjoy cooling off in the private pool area, which overlooks the beautiful lake. You can also lounge in the shaded lanai or watch TV in the living room.

This vacation rental has enough living space for a total of eight guests. It features two bathrooms, a family room, a breakfast nook, and an overstocked kitchen. Amenities such as air conditioning and Wi-Fi are provided as well.

Kissimmee, Florida, United States
PRIVATE VACATION HOME 8 Guests 4 Bedrooms 2 Bathrooms

Top guest reviews
Location:
it was in a beautiful tranquil location situated a nice distance away from the busy tourist spots
Cleanliness:
the property was clean and decent
it was very clean and well taken care of
Amenities & Room:
the pool was great and had a beautiful view across the lake to the tree line
also someone always responds to emails within mins and the view from the pool was great
Read more reviews

46. Family-friendly villa with a game room

Highlights Family Friendly Convenient Location

Best for: Families with kids and infants, group stays

Featuring a convenient location close to theme parks, restaurants, and shops in Kissimmee, this luxurious villa provides a great stay for you and your family. Staying in this rental provides you access to a fitness center, cyber café, and clubhouse. If you want to relax without leaving the premises, the best way is to soak in the rental’s private pool. This amenity can be heated for extra comfort. There is a spa whirlpool on the property as well.

The place is perfect for a total of eight guests. There are four bedrooms, three full bathrooms, and a game room. For families, a high chair and a travel crib are provided for convenience. Other amenities include Wi-Fi, air conditioning, and a cable TV.

Kissimmee, Florida, United States
PRIVATE VACATION HOME 8 Guests 4 Bedrooms 3 Bathrooms

Top guest reviews
Host:
property owner was prompt with responses and took care of any thing i needed right away
communication with the owner was easy and made planning a breeze
Location:
amazing property great location and neighborhood
the price was right location was perfect walmart restaurants theme parks all within minutes
otherwise things were great great pool house and location was easy to get to all the parks
Cleanliness:
property was exceptionally clean and comfortable
house was very clean and well stocked
this property was nice clean and quiet
everything was very clean and in good repair
remember to bring your cleaning products toilet paper garbage bags and kleenex/napkins/towels if you want to clean
Read more reviews

47. Homey sanctuary with forest views

Highlights Family Friendly Golf Course Access Nature Retreat

Best for: Reunions, golf enthusiasts, families with kids

Create happy memories with your loved ones while staying in the Eva Kingdom. This beautiful vacation rental offers a private pool and spa, both situated on a furnished deck overlooking the forest. The pool deck also includes lounge chairs, tables, and other pool furniture. If you prefer, you can also have the pool and spa heated during your stay. The heater runs from 9am to 9pm once turned on.

Inside the rental are 4 bedrooms and 3 full bathrooms, ideal for accommodating a total of 12 guests. The place also has modern amenities such as WiFi, air conditioning, cooking basics, and TVs.

Kissimmee, Florida, United States
PRIVATE VACATION HOME 12 Guests 4 Bedrooms 3 Bathrooms

Top guest reviews
Host:
everyone is super friendly
Location:
the location was close to all amusement parks
but other then that the location was great for everything
Cleanliness:
house was clean and lots of room
i took pictures and suggest they need to clean or hire new cleanup crew asap
clean house that has plenty of room for the family
the beds where comfortable and house very spacious
Amenities & Room:
the owner just need to throw the whole inside-furniture appliances and entertainment room away and try it again
Read more reviews

48. Four-bedroom villa in an exclusive community close to theme parks

Highlights Nature Retreat Family Friendly Work Travel Wheelchair Friendly

Best for: Outdoor enthusiasts, families with kids and infants, group stays

This spacious four-bedroom villa offers you a comfortable home during your Kissimmee vacation. It’s big enough to accommodate up to 10 people and features top-notch amenities such as an 86-inch smart TV, a pool table, and high-speed wireless internet access.

The large deck area where you’ll find the pool and spa, as well as a grill and several lounge chairs, is fully screened so you won’t have to worry about bugs. You can request for the pool and spa to be heated for an additional USD 33 per day, for a minimum of 4 days.

The property is located in the gated community of The Bella Vida Resort, which also offers great facilities and amenities including a clubhouse, a swimming pool, a fitness center, an arcade room, gardens, and access to several lakes. Furthermore, restaurants, shops, golf courses, and popular theme parks are all within easy reach.

Kissimmee, Florida, United States
Wheelchair accessible Visual Aid: Braille
villa 10 Guests 4 Bedrooms 4 Bathrooms

Top guest reviews
Host:
he was quick with email responses and very helpful
dealing with tony the owner is a pleasure and he answers questions (emails) almost instantaneous
owner was greatly helpful and always available for any questions we had
villa owners were extremely pleasant to deal with
tony was responsive in answering all our questions prior to the stay
Location:
the location is perfect a short distance off the 192
the resort was beautiful location was very convenient
the location was excellent we only had a short drive to disney and universal studios
was great to have so many businesses close by as well
this is a lovely spacious villa which was on a lovely gated community in a great location
Cleanliness:
everything was clean and neat
its spotless and very well kept
the pool & hot spa were fantastic as well as being clean
the place is very clean and well appointed
the house was clean and tidy and of a good size
Amenities & Room:
very nice patio area with good size pool and jacuzzi
this is a superior house 4 double bedroom with 4 ample size bathrooms
Read more reviews

49. Lakeside villa in peaceful locality

Highlights Family Friendly Waterfront Luxury

Best for: Nature lovers, families with kids, group stays

This lakeside villa is located in Kissimmee’s Eagle Pointe community. At this rental, you can spend hours at the screened pool, either swimming or lounging next to it. There is a smaller, shallower section as well, so your little ones can splash around without your supervision. The soaking tub in the bathroom is another spot that you and your kids can enjoy.

To add to your indoor entertainment, there is a games room onsite. It is appointed with a ping-pong table, dartboard and several other facilities.

Kissimmee, Florida, United States
villa 9 Guests 4 Bedrooms 2 Bathrooms

Top guest reviews
Host:
the management was very responsive with two requests and friendly
the property manager was friendly and could be reached if needed
Location:
the location and house will not disappoint
the villa is in a great location with all needs taken care of
beaches are not too far away and lots of great places to eat locally
Cleanliness:
very clean jans cozy
very clean and welcoming
lovely house very clean the pool is just perfect
the house was very clean we would definitely stay here again
neighborhood was very quiet pool was very nice and clean
Amenities & Room:
it was perfect i'd rather have had the garage vs an non-air conditioned "game room" but overall very spacious
the beds were very comfortable too which never happens in a hotel
the home itself was very comfortable and had all the necessary amenities
Read more reviews

50. Modern private home with top-notch amenities

Highlights Family Friendly Convenient Location

Best for: Group stays, families with kids

This Kissimmee vacation rental has three bedrooms that can sleep up to six guests, which is great for families and small groups of friends. It is fully furnished with all the essentials to make your stay as comfy as possible. The kitchen, for instance, has a fridge, an oven, a stove, and more so you won’t have any problems preparing your meals. It has a game room with a pool table for indoor activities. Plus, the backyard features a pool with loungers, the perfect spot to relax under the warm sun.

Make this amazing vacation rental your home base for your Kissimmee adventures. It’s close to several points of interest in the area including a Medieval Times restaurant, Kissimmee Sports Arena and Rodeo, Osceola Heritage Park, and more.

If you drive a few minutes northward, you’ll get to some of Orlando’s top attractions including SeaWorld and Disney World.

KISSIMMEE, FL, US
6 Guests 3 Bedrooms 2 Bathrooms

51. Chic lakefront home with pool

Highlights Family Friendly Waterfront Wheelchair Friendly

Best for: Nature lovers, families with kids and infants, group stays

This private lakefront home is a 5-star accommodation for Kissimmee visitors. It’s big enough to accommodate up to eight guests, which is more than enough to fit a family. Some great amenities to enjoy here include air-conditioning, high-speed WiFi, a console, a TV, and a well-equipped modern kitchen. To top it all off, the large fully screened backyard is equipped with a heated pool—a beautiful outdoor area where you can relax and enjoy the beautiful lake view.

If you’re looking to explore what Kissimmee has to offer, this place is conveniently located close to many of the city’s popular spots. Restaurants, shops, and other commercial establishments are within minutes of the property. Drive a bit farther and you’ll find some of Orlando’s popular theme parks including Disney World and Universal Studios.

Kissimmee, Florida, United States
Wheelchair accessible Visual Aid: Braille
PRIVATE VACATION HOME 8 Guests 4 Bedrooms 2 Bathrooms

Top guest reviews
Host:
the owners were very prompt and responsive to our needs
it was a relief to have a host so responsive
the owners were great to work with and made everything very easy
communication with the owners was fast courteous and accommodating
highly recommended property and great communication with the owners
Location:
the location was excellent
it was close to everything but not in the chaos of the area
close to restaurants shopping and short distance to amusement parks
great location we loved the pool
great location 15 minutes to disney 25 to universal
Cleanliness:
very clean very nicely decorated
the pool was sparkling clean and warm
everything was clean and so perfect for our little family
the property was very clean and comfortable
very clean very spacious beautiful home
Amenities & Room:
the pool was beautiful and the view priceless
all of this could be viewed from the living room couch thanks brian and amy
the view of the lake is stunning and we loved the pool
things like baseboards a hair in the corner of the water closet in the en suite bathroom
the lake view is amazing and the swimming pool is good clean and heated as well
Read more reviews

52. Lovely two-story lakefront home with screened lanai and heated pool

Highlights Family Friendly Wheelchair Friendly Waterfront

Best for: Reunions, nature lovers, families with kids and infants

This lovely home will surely make your Kissimmee vacation more memorable. Its lakefront location offers not just a relaxing vista but a tranquil vibe as well. It features a screened lanai with a heated pool, providing you with a great outdoor space for enjoying the scenery. You can spend quality time with your family out in the sun without having to worry about bugs invading your happy place.

The property is big enough to accommodate a family or a group of up to twelve people. It’s fully furnished with everything you’d expect from a modern home including a fully equipped kitchen, air-conditioning, heating, WiFi, and more. Keep in mind, though, that the property only offers a six-night minimum stay to book, so make sure you’re planning to stay for maybe a week.

Kissimmee, Florida, United States
Wheelchair accessible Visual Aid: Braille
PRIVATE VACATION HOME 12 Guests 5 Bedrooms 3 Bathrooms

Top guest reviews
Host:
the host was outstanding thank you for everything mr
local property managers were also responsive
the pool was great the house is amazing and the host juan was very accommodating highly recommended
estrada was helpful above and beyond throughout the entire process
Location:
it in a great location to both disney and universal studies
plenty of room and located close to all the main attractions
the location was convenient to all of orlando’s popular attractions
nicely situated in a quiet neighborhood--close to shopping parks and other activities
this was an excellent location and accommodation for our family
Cleanliness:
a ver clean and comfortable space to be
it was very spacious and clean
the home was spotlessly clean and well maintained
the house was super clean when we arrived all the theme parks are very close to here
Amenities & Room:
the rooms and beds were very large and comfortable
Read more reviews

53. Comfortable accommodation with homey amenities

Highlights Family Friendly Wheelchair Friendly Convenient Location

Best for: People with access needs, families with kids, group stays

Consider booking this rental if you’re looking for a home away from home in Kissimmee. Stocked with linens, towels, toiletries, kitchen appliances as well as laundry facilities, this house ensures a comfortable stay for its guests. Plus, the main bathroom features a soaking tub, where you can draw up a fun bubble bath for your little ones.

You can use the private pool to energize yourselves on a hot summer afternoon or pay extra to get it heated for full-blown relaxation. Some pool toys and inflatables have also been made available for your use.

Kissimmee, Florida, United States
Wheelchair accessible Visual Aid: Braille
villa 6 Guests 3 Bedrooms 2 Bathrooms

Top guest reviews
Host:
property was very nice property manager was super helpful
the owners are amazing to talk to and respond very quickly
we were able to check in early after communicating with the owner so that was really appreciated
hosts very responsive to our request to stay next winter
house was clean on arrival and the owner was super responsive
Location:
great location for shopping and restaurants
great location and close to all the attractions
the location to disney and universal was perfect
we had plenty of privacy and the neighborhood is super quiet
the neighborhood's very quiet and the houses are well kept and seem to be occupied which is nice
Cleanliness:
it looked like it hadn’t been cleaned in months
the house was nice the master bathroom wasn’t cleaned real good when we arrived
Amenities & Room:
beautiful home equipped with more than enough amenities the private pool was so refreshing in the florida heat
loved the privacy of the fenced in pool
pool was nice for us to swim lots of floats for people to use of all ages
Read more reviews

54. Luxurious lakefront family villa

vrbo
Source: vrbo
Highlights Luxury Family Friendly Waterfront Pet Friendly

Best for: Pet parents, luxury travelers, families with kids, reunions

This beautiful five-bedroom villa, situated beside a lake with a fountain, comes with all the amenities needed for a luxurious vacation. It can comfortably house 11 people. There’s a fully equipped kitchen, spacious living and dining area, a charcoal grill, free WiFi, digital entertainment, linen, and laundry facilities. The star attraction of the house is the huge, clean pool where you can relax and swim in privacy.

Kissimmee, Florida, United States
PRIVATE VACATION HOME 11 Guests 5 Bedrooms 4 Bathrooms

Top guest reviews
Host:
very responsive management company to any questions we had
renting was easy correspondace with the owner was a plus and we certainly felt like we were welcome
Location:
we love this place location and neighborhood
great location beautiful home and gorgeous decor we felt at home and comfortable in this property
Cleanliness:
the property was super clean the linen and towels smell so good
the house was very clean
very relaxing the place was very clean which was important to us
this house is well stocked and clean
me and my family felt like we were home the pool was clean the kids enjoy it
Amenities & Room:
some i gave up on but it was still awesome having tvs in every room and outside
great rooms entertainment w tvs all over the house including out on the pool side
we were able to enjoy the pool and pool table during our off time
the pool was nice and warm for the kids loved this house thanks xedxb8x8a
Read more reviews

55. Vacation home with hot tub

Highlights Family Friendly Wellness

Best for: Families with kids and infants, group stays

You can consider checking into this neat rental located in a lovely neighbourhood in Cumbrian Lakes. Here, you can cool off in the private, screened pool shaded by a transparent wall affording views of the charming outdoors. Else, you can enjoy a warm, soothing soak in the private hot tub. After you’re done, you can enjoy quality family time thanks to the wide range of recreational options including board games, foosball, air hockey table, pool table and more.

Free, high-speed internet connection ensures that you remain connected to the world for work as well as leisure.

Kissimmee, Florida, United States
villa 8 Guests 4 Bedrooms 3 Bathrooms

Top guest reviews
Host:
very responsive management company
the host was a good communicator and made sure all my issues were addressed
Location:
it was a good location and all amenities were close by
Cleanliness:
the bathrooms were clean and comfortable to use
upon arrival the home was clean everything was as described in the listing
it was clean close to universal and disney and had everything that we needed
Amenities & Room:
very spacious and comfortable we have 7 people in our group
it was well stated this prop doesn’t provide things like washcloths paper towels toilet paper dish soap etc
Read more reviews

56. Single-story Lake Berkley home

Highlights Family Friendly Budget Friendly Good Neighborhood Nature Retreat

Best for: Budget travelers, families with kids, group stays

This budget-friendly vacation rental in Kissimmee is located in a private, gated community. Staying at the property is ideal for families with young ones since there are plenty of entertainment amenities like the game room with a billiards table, a dartboard, a play area, and many more. The 24-hour Walmart is 2 minutes from the property, and guests who wish to make use of the full kitchen may do so. Outside, there is a screened-in and heated swimming pool with a shaded seating area.

Kissimmee, Florida, United States
villa 10 Guests 5 Bedrooms 3 Bathrooms

Top guest reviews
Host:
betina and annette were very helpful in the many questions i had
i had a chance to meet the owners and they ere very friendly
the owner was 100% correct and very gentle
friendly gate people
even the guard at the gate was very helpful in giving directions to the many different attractions
Location:
the location was great - so close to shopping and eating
very good location close to restaurants and dinner shows
all very accessible and easy to get to from the location
perfect for big family great location would recommend to everyone vacationing with 6 or more people
also we visited several attractions in the area all very close to the villa -- easy
Cleanliness:
everything was clean and very nice
the property was clean and comfortable
it had plenty of space and the house was clean and well maintained
upon arrival at this villa the overall appearance was neat and clean
the home was clean and well maintained and we did not expereience a single issue during our stay
Amenities & Room:
the pool was perfect - nicely heated for the little ones
easy wifi access comfortable rooms and eat instruction manual that answered all other questions
my families stay was so much more comfortable and enjoyable because of it
this property was awesome we were 5 adults and 5 kids it was spaciuos with enough room for everyone
Read more reviews

57. Well-appointed home near Walt Disney World® Resort

Highlights Luxury Family Friendly Good Location

Best for: Luxury travelers, families with kids, reunions

This beautiful home in Bellavida Resort is just a 10-minute drive from Walt Disney World® Resort. You will find all the facilities you need for a comfortable stay. The full kitchen is ideal to prepare meals if you don’t want to spend a buck dining out. Additionally, laundry essentials have been provided so you need not pack heavy.

The best part about this rental is that once you return after a long day of activities, you can plunge into the private pool or the whirlpool tub to rid your body of all the exhaustion. The pool can also be heated for an extra fee. The host also offers a barbecue set up for additional charges, so you can carry out a fun cookout.

In addition to the in-unit amenities, you can make use of the facilities at the resort’s clubhouse and keep yourselves thoroughly entertained. These include the community pool, whirlpool tub, gym and reading room, among others.

Kissimmee, Florida, United States
villa 12 Guests 4 Bedrooms 4 Bathrooms

Top guest reviews
Location:
great location very quiet neighborhood
the location of the home is great to get to any destination in the area
Cleanliness:
house was clean for the most part
it was very clean and pool was perfect for kids
clean and huge lots of room for my family
thank you for the cleanliness
Amenities & Room:
there was definitely enough room for all of us
Read more reviews

58. Chic home with resort clubhouse access

Highlights Family Friendly Luxury Waterfront

Best for: Nature lovers, reunions, families with kids

When visiting Kissimmee, consider booking this chic and stylish home in Sonoma Resort that provides access to a range of resort amenities, including a clubhouse, a gym, and a gorgeous communal pool that overlooks a lake. The house has a screened private pool, a spa, a barbecue grill, and ample sun loungers to enjoy the Floridan outdoors. The interior of the house has a modern, chic and minimalist decor in the living room, open-plan kitchen and dining area, luxe bedrooms, stylish family room, and sleek bathrooms. All the attractions of the area, including theme parks, nature parks, restaurants, and more are at a short driving distance from this home.

Kissimmee, FL, US
28 Guests 13 Bedrooms 0 Bathrooms

59. One-story accommodation with a pool and spa

Highlights Family Friendly Wellness

Best for: group stays, families

This one-story vacation rental is ideal for families or a group of up to 10 guests. There are 4 bedrooms, two of which are themed and suitable for kids. There are also 3 full bathrooms as well as a well-equipped kitchen. Aside from the smart TVs equipped in every bedroom, there is also one in the game room. There are game tables and a game console available as well. Other amenities also include WiFi and air conditioning.

The best part about staying in this rental is that guests can enjoy a private pool and a spa. For a fee, the pool can be heated. This amenity is set in a screened area of the property, providing guests with privacy during their stay.

8 reviews   Wifi Available
House 10 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 10
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Host:
the owners are very responsive and helpful
Cleanliness:
the home is very clean and very well decorated
Read more reviews

60. Vacation home with lanai overlooking a private pond

Highlights Family Friendly Unique Theme Nature Retreat View

Best for: Families with kids, group stays

Indoor and outdoor fun are aplenty at this Mickey Mouse-themed vacation home in Cumbrian Lakes. Its centrally air-conditioned interior features a game room where your crew can battle it out over pool and ping pong games. Huddle in the family room with 55-inch cable TV for movie nights or enjoy your favorite shows privately in any of the bedrooms with smaller cable TVs.

Outside, a gorgeous lanai overlooking a tropical forest and pond awaits to charm your fun-seeking spirit. There’s a large pool that can be heated for an extra 30 USD per day to enjoy as well as a deck with four sun loungers. A private hot tub is also in this alfresco space to soothe your tired muscles. Note that the property has a five-night minimum stay policy.

Kissimmee, Florida, United States
Wheelchair accessible Visual Aid: Braille
villa 8 Guests 4 Bedrooms 3 Bathrooms

Top guest reviews
Host:
the kids loved the disney room and enjoyed the toys provided by the host
Location:
this was great place and location
Amenities & Room:
the beds are very comfortable we all slept incredibly well
Read more reviews

61. Cozy villa with a screened pool

Highlights Family Friendly Budget Friendly

Best for: Group stays, families with kids

This cozy villa is meticulously furnished in vibrant colors and offers warm and cozy living spaces for relaxation. Its grandiose kitchen is perfect for indulging your inner chef in a culinary adventure and trying new delicacies. You can whip up quick snacks and pair them with the best selection of wine as you lounge by the pool.

The pool is covered by a glass screen that overlooks a beautiful lush yard and other rentals in the vicinity. It receives a healthy amount of sun, perfect for lounging and enjoying a warm soak. If you wish to enjoy a late-night swim, put in a request with the host for a heated pool at the time of booking.

Kissimmee, Florida, United States
villa 6 Guests 3 Bedrooms 2 Bathrooms

Top guest reviews
Location:
it is a great location just minutes from walmart
good location for all the parks and shopping
but a great location property is very worn
ideally located for the theme parks and found the estate to be nice and quiet
ideally located for the theme parks and found the estate to be nice and quiet
Cleanliness:
very clean and well maintained
it was clean and well maintained
everything was clean and ready for us
the neighbors are quiet and the house is beautiful and clean
Amenities & Room:
very comfortable and all the necessary facilities
very comfortable and all the necessary facilities
Read more reviews

62. Deluxe pool home

Highlights Family Friendly Waterfront

Best for: Nature lovers, families, group stays

A beautiful four-bedroom house, it comes with air conditioning, internet, laundry facilities, and a well-equipped kitchen. The master bedroom opens onto a lovely pool deck. Spend your mornings sipping coffee as you watch big Florida birds fly over the lake. Have fun in the well-maintained swimming pool with seating around it. Sunbathe on a lounge chair or have your meals at the table by the pool. You can also play foosball and ping pong in the garage or have a relaxing soak in the garden tub.

Kissimmee, Florida, United States
Wheelchair accessible Visual Aid: Braille
PRIVATE VACATION HOME 8 Guests 4 Bedrooms 2 Bathrooms

Top guest reviews
Host:
the key lock box was not secure & the pool net was torn)
The pool was a big hit with my girls
We have already booked for next year
Overall the property was nice and exactly as advertised
Beautiful clean updated home Beds were super comfortable
Location:
Very lovely house in a great location
I liked the quiet neighborhood
The house Is very close to Disney World and a good base for exploring the area (including the Kennedy Space Centre which is well worth a visit)
Location was ideal for visiting parks or shopping
The neighborhood was quiet and peaceful
Cleanliness:
everything was clean and everything we needed
The villa was clean spacious and had everything we needed
The place was clean and well equipped
and we were amazed with your house
Amenities & Room:
This property looked exactly like the pictures
the kids enjoyed the pool
It was great to have access to a grill and not have to had to pay extra to use it loved having access to the pool from the master bedroom
It was clean inside and out with a well equipped kitchen plenty of outside space some of which is covered which is handy when it rains It has a lovely lake view with an abundance of wildlife
The only thing is I wish they would have provided a few more trash bags
Read more reviews

63. Large home with kid-friendly amenities

Highlights Family Friendly Nature Retreat

Best for: Outdoor enthusiasts, families with kids, group stays

This deluxe home is strategically located in the Indian Point neighborhood. It sits in a quiet conservation area teeming with wildlife yet easily accessible from several theme parks, shops, and restaurants within minutes. The property also affords to provide access to community amenities such as a kids’ play area, tennis courts, and a large pool.

But you don’t have to actually share a pool with strangers as this rental features a solar-heated swimming pool surrounded by ample lounge chairs, so you can leisurely bask under the sun. Don’t miss out on the fun indoors as there are five flat-screen cable TVs, a game room, and free speedy WiFi for entertainment. Guests with toddlers can take advantage of the available travel crib, highchair, and stroller.

Kissimmee, Florida, United States
Wheelchair accessible Visual Aid: Braille
villa 8 Guests 3 Bedrooms 2 Bathrooms

Top guest reviews
Host:
thank you to the owners - the daleys
very friendly house management staff
Location:
great central location - close to disney sea world etc
nice house in a good quiet neighborhood
Cleanliness:
the villa was clean and very well layed out with the relaxing pool and pool table
Amenities & Room:
our family enjoyed having a private pool and plenty of space to spread out
easy process lots of beds for large families
Read more reviews

Fall in love with Kissimmee

Kissimmee is the place where all your holiday dreams can come true. Once you’ve been here, you’ll keep returning for the excitement, joy, Disney magic, and natural beauty. And whether you’re looking for lakefront homes or beach house rentals with a private pool, plenty of amazing accommodation options are available in Kissimmee.

Frequently asked questions about Kissimmee vacation rentals with a private pool

Which Kissimee vacation rentals with a private pool have nice views?

Which Kissimee vacation rentals with a private pool are good for families?

Which Kissimmee vacation rentals with a private pool have a gym?

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Seema Misra is an artist and writer. She has over nine years of experience in various writing fields including instructional design, editing, technical writing, business writing, travel writing,...View profile

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