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17 Vacation Rentals With Private Pools In Kissimmee, Florida - Updated 2020

kissimmee vacation rentals with private pool
Seema
Seema
Updated

Kissimmee, Florida is perfect for family vacations at theme parks, a getaway with friends, or just a romantic outing with your partner. This family-friendly town is within a few minutes’ drives 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 also a lot on offer for nature and adventure lovers. You can zip through treetops, 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. Do these attractions make you want to visit Kissimmee this year? Here is a list of 17 vacation rentals with private pools in Kissimmee, Florida.

1. Spacious home away from home (from USD 108)

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.

SUPERB POOL HOME CLOSE TO DISNEY
32 reviews
bungalow 6 Guests 3 Bedrooms 2 Bathrooms
Top guest reviews
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
Cleanliness:
It's lovely clean and spacious with a great pool
we were so pleasantly surprised at how spacious and inviting the home looked
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
Read more reviews

2. Luxurious lakefront family villa

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.

Exquisite Destination. Disney Vacation Homes. Central to All Major Attraction
99 reviews
House 11 Guests 5 Bedrooms 5 Bathrooms
Top guest reviews
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
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
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
Read more reviews

3. Centrally located six-bedroom holiday villa

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.

Beautiful 6 Bed Gated Pool Home At Aviana Resort
24 reviews
House 12 Guests 6 Bedrooms 5 Bathrooms

4. Deluxe pool home (from USD 145)

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.

Luxury Lakefront Pool Home - Only 15 Minutes to Disney World
38 reviews
House 8 Guests 4 Bedrooms 2 Bathrooms
Top guest reviews
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
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
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
Read more reviews

5. Cozy pet-friendly waterfront home (from USD 97)

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 vacation rentals with a private pool is the south-facing, private, screened pool and Jacuzzi overlooking a scenic pond.

Pet Friendly 3 Bedroom/2 Bath Home,Games Room, Private Pool & Spa.
55 reviews
House 7 Guests 3 Bedrooms 2 Bathrooms
Top guest reviews
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
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
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
Read more reviews

6. Beautiful seven-bedroom lake house (from USD 186)

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. You also have a private pool and spa with heating.

The Lake House! 7Br 4.5ba with private pool!
Kissimmee, Florida, United States
232 reviews
Entire house 10 Beds 7 Bedrooms 4 Bathrooms
Top guest reviews
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
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
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
Read more reviews

7. Unforgettable vacation home near Disney World (from USD 230)

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.

Luxury near Disney - Pool Home
Kissimmee, Florida, United States
173 reviews
Entire house 8 Beds 6 Bedrooms 5 Bathrooms
Top guest reviews
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
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
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
Read more reviews

8. Gorgeous four-bedroom townhome in Storey Lake Resort (from USD 196)

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.

Minutes To Disney, Private Pool, Amenities,PEQ3141
Kissimmee, Florida, United States
48 reviews
Entire townhouse 6 Beds 4 Bedrooms 3 Bathrooms
Top guest reviews
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
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
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
Read more reviews

9. Comfortable three-bedroom house with a pool (from USD 68)

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 jacuzzi. 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.

Luxury 3 bedroom villa with private pool
2701 shortleaf court
villa 6 Guests 3 Bedrooms 3 Bathrooms

10. Great vacation home near Disney World (from USD 100)

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.

GAMEROOM, BBQ GRILL, FREE WIFI, ONLY MINUTES FROM DISNEY!!
1539 Indian Oaks Trail
2 reviews
House 8 Guests 4 Bedrooms 2 Bathrooms

11. Well-appointed home with easy access to theme parks (from USD 265)

Suitable for large families or groups of friends on a vacation in Florida, this eight-bedroom, six-bathroom home can accommodate up to 18 guests. It has a very luxurious interior consisting of a well-appointed living area, a large dining area, a full kitchen, a game room, lavish bedrooms and elegant bathrooms. A gorgeous private pool, a spa, and an outdoor deck with seating are available too. Guests even have access to the resort’s facilities like a massive swimming pool, a clubhouse, and a kids’ play area. Many of Orlando’s famous theme parks are a short drive away from this property.

Luxury Disney Dreamers Wonderland @Windsor Westside Resort,Private Pool,GameRoom
48 reviews
House 20 Guests 8 Bedrooms 6 Bathrooms
Top guest reviews
Amenities & Room:
well appointed; comfortable amenities
the home is great air conditioned game room pool an amazing supply of pool toys
Cleanliness:
the house was very clean and spacious
the pool at the house was impeccably clean and warm
it’s a beautiful home and very clean
wonderful property well kept and clean
beds were comfy and bathrooms clean
Location:
great location for large group to enjoy all attractions in the area
great location close to attractions yet had a feel of being away from the crowds
large rooms and we would definitely come back you are 20-25 min from parks but drive is easy
Read more reviews

12. Luxurious home in a gated community (from USD 182)

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.

6BR/4.5B, Private Pool/SPA, 10mi Disney. Amazing!
Kissimmee, Florida, United States
231 reviews
Entire villa 11 Beds 6 Bedrooms 4 Bathrooms
Top guest reviews
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
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
Host:
also the host was great
hosts were 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
Read more reviews

13. Stylish townhome with amazing amenities (from USD 110)

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.

4-bedroom house w/ private pool - lovely location
Kissimmee, Florida, United States
40 reviews
Entire house 5 Beds 4 Bedrooms 3 Bathrooms
Top guest reviews
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
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
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
Read more reviews

14. Gorgeous villa for a large group (from USD 236)

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.

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

15. Disney-themed townhome in a resort (from USD 259)

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.

Near Disney 4BR Family Resort Home - Private Pool!
1 review
townhome 10 Guests 4 Bedrooms 3 Bathrooms
Top guest reviews
Cleanliness:
upon check in the house was clean and smelled amazing
Read more reviews

16. Chic home with resort clubhouse access (from USD 580)

chic home with resort clubhouse access
Source: www.vrbo.com

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.

14 Bedrooms Luxury Home at Sonoma Resort Kissimmee
Kissimmee, FL, US
28 Guests 13 Bedrooms 0 Bathrooms

17. Townhome with access to resort amenities

Stay at a lovely townhome in Kissimmee that can comfortably sleep 10 guests in its 4 bedrooms. The house has a well-appointed living room, a modern kitchen, a lovely dining area, and spacious bedrooms and bathrooms. A private pool with a patio and seating are also available for guest use. Resort amenities like a clubhouse, an arcade, a market shop, a massive pool, a fitness center, and more are also accessible to guests staying at this property. Walt Disney Resort is just 5.5 mi (8.9 mi) away.

Full-service Tiki Bar / Water Slide / Fitness Center / Movie Theater / Near Disney /Free Resort Fees
13 reviews
townhome 10 Guests 4 Bedrooms 3 Bathrooms
Top guest reviews
Amenities & Room:
kids loved the heated pool
the kitchen area is great size for families
both couples had rooms with king beds and the trundle beds worked perfect for the kids
Cleanliness:
full kitchen everything clean and new
Host:
the staff and everyone were really helpful and kind
Location:
we loved our stay the house was located close to everything we wanted to do
we loved how close it was to disney parks
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.

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,...Read more

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