8 Vacation Rentals In Kissimmee, Florida - Updated 2024

Contributing Writer
| 5 min read

Kissimmee is an ideal destination for family trips and group vacations. The unexplored adventurous activities and a wide array of popular theme parks have made the city more popular among tourists from all over the world. The Disney theme park and water parks in this city are here to excite the kids while thrilling endeavors are available to delight the adventure seekers. Universal Orlando Resort, Walt Disney World Resort, and SeaWorld Orlando are located in close vicinity of the city. Zipping via treetops, sliding through the Everglades headwaters, and flying high on a hot air balloon are some of the best activities to try in this amazing city of Kissimmee. The Florida Mall and The Mall at Millenia in Kissimmee offer the perfect shopping experience to visitors. Other must-visit places also include Lake Tohopekaliga and Windsor Hills Resort, which is a gated community in Central Florida offering amazing community amenities. To make you choose the right accommodation, we offer you the top vacation rentals in Kissimmee.

We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on June 25, 2024.

1. Three-bedroom large villa in Kissimmee (from USD 110)

This luxury villa is located amidst a residential area in the Lakeside Estate. The villa’s prime location near the city center, supermarket, pharmacy, and gas station makes it convenient and comfortable for the guests. Disney World and Universal Studios can be reached within a 20 to 30-minute drive from the villa. Orlando International Airport is just a 17-minute drive away. A work desk, Wi-Fi, a TV, central heating, a washer, a dryer, a safety lock box, and bathroom necessities can be found in the villa. A beautiful pool area and a well-equipped kitchen are also available for use.

Stayed at this property?
Kissimmee, Florida, United States
5.32 km (3.4 mi) from Kissimmee Lakefront Park
209 reviews   Superhost Wifi Available
ENTIRE HOME 6 Beds 8 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
beds were super comfy and linen like new
the showering facilities were perfect the open planned area was huge
very nice place with a lot of space and room in a quit neighborhood
there is plenty of room and a nice pool
very clean and friendly place to stay
it was very clean and the pool was a plus
the pool was covered and clean
the villa was spacious clean and airy
the beds were comfortable and the pool nice and clean
the owner is really friendly and helpful
highly recommend the host and the property
mr raymond was a wonderful host
host was very easy to deal with
raymond was a great host
the location is fantastic
the location was good
close to all the major attractions
great location for activity like
shopping was nice and close as well
Read more reviews

2. Charming lake home (from USD 378)

This 3275-square-foot (304-square-meter) dream rental is designed with luxury and opulence. The kitchen in the house includes a dishwasher, refrigerator, microwave, coffee maker, and toaster. The house is furnished with high-end amenities like a private pool, a spa, an outdoor grill, a fitness room, and a dining area. A beautiful lawn area soothes the mood of the guests and makes it a perfect place to spend leisurely evenings. A foosball and ping-pong table along with various other fun-filled games in the entertainment room is ideal for family fun. In addition, staying in this rental also comes with access to the Clubhouse Resort, which features a restaurant and swimming pools with a lazy river. The house has a perfect location near Disney, Disney Springs, dining options, and shopping areas.

Stayed at this property?

8.7 km (5.5 mi) from Kissimmee Lakefront Park
40 reviews   Wifi Available
House 16 Guests 6 Bedrooms 5 Bathrooms

Accommodates: 16
Minimum Nights: 0
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
There was plenty of room for everyone
The children enjoyed the game room and pool as well as the bunk-bed arrangement
The house is immaculate great open spaces
everyone felt like they had plenty of space and
Additional fees tacked on for heating pool and use of the grill was pretty weak Should not be
no can opener tea towels dish cloth
Again instructions re recycling of waste
However the owner responded quickly to our emails; and refunded the additional charges for grill and pool heating
Splash pool is awesome full size gas grill
We had a minor issue that needed fixing and they were very responsive and super friendly
The added benefit was the common pool area with a very nice pool and lazy river
Convenient to all parks but need lots of quarters as there are tolls everywhere
No plastic glasses to use around pool area
No instructions regarding tv usage and lots of remotes to choose from or instructions about where to put trash or hours for community center or events at the center
Manager got right back to me on every email on the way down-
The resort water park is wonderful Daily trash pickup is a plus as well
Read more reviews

3. Four-bedroom gated resort for families (from USD 175)

This luxury villa features a wonderful location only 8 km (5 miles) from Disney World and 3.2 km (2 miles) from plenty of shopping destinations and restaurants. The family room has a 58-inch LCD TV. The kids can have a great time with the game consoles available in the two bedrooms of this lovely villa. It is crafted elegantly with leather, natural stone, and wood furnishings. This gated facility provides secure accommodation for the guests. Staying in this upscale vacation home also comes with access to pool and workout center.

Stayed at this property?

6.68 km (4.2 mi) from Kissimmee Lakefront Park
99 reviews   Wifi Available
villa 10 Guests 4 Bedrooms 2 Bathrooms

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

Top guest reviews
Amenities & Room:
Each bedroom has a TV in addition to the large one in the living room
very comfortable living environment and the pool was great
You will find three lounge chairs by the pool and a lovely tile topped table that sits 5
In the house you will also find two pack & plays and portable high chairs that you affix to the dining table
This four bedroom house is decorated with Paris/French themed prints understated but very elegant without being intimidating It is furnished with everything you need - towels; bed linens; dishes ...
He responds to all requests and enquires very quickly and provides you clear concise instructions
the house was immaculate and the pool was great Very close to Disney attractions and about a half hour drive with traffic to Universal Studios
In addition to the home the community clubhouse offers tons of amenities from pool to hammocks children's play area gym sauna hot tub and a movie night
You will find two grills both looking very new there For families traveling with small children there are two clean strollers
Home was very clean and well stocked
It was amazing we loved every minute of it
It is like walking into a lovely apartment in the Rue de la Paix in Paris
lose to SeaWorld and Aquatic Orlando WILL use the home again
Read more reviews

4. Venetian Bay Villages Resort (from USD 122)

Venetian Bay Villages Resort is an incredible accommodation with a stunning lake view. Universal Studios is just 24.1 km (15 miles) away from the resort while Walt Disney World can be reached within a 20-minute drive. It’s the perfect vacation rental for family vacations as there are outdoor swimming pools, two tennis courts, pool tables, a volleyball court, a kids’ play area, a fitness center, and a barbecue area. In-unit features also include Wi-Fi, air conditioning, a cable TV, and a DVD player. The guests will feel secure in their 24-hour gated security premises. For shopping freaks, there are Orlando Premium Outlets within 16 km (10 miles) from the resort.

Stayed at this property?
Kissimmee, Florida, United States
4.56 km (2.9 mi) from Kissimmee Lakefront Park
Wheelchair accessible Visual Aid: Braille
villa 6 Guests 3 Bedrooms 2 Bathrooms

Top guest reviews
Amenities & Room:
the condo had all the amenities that we needed even coffee filters plenty of space when our daughter and 2 children visited
It was nice having 2 bedrooms upstairs
The home is stocked with all that's needed to prepare meals
We totally enjoyed our stay in this town home One of the polls is right across the parking lot from the home
The beds were comfy heated pool and hot tub located right outside of our door
It was clean and spacious
Our unit was spacious and beautifully decorated
The resort itself is very very well presented and clean
Upon arrival the smooth check in were a plusThe apartment were very clean And comfortable
The home was clean and spacious for our family of 4
The owner was in contact with us which made everything so personable
gated community pool was great overall super experience
Mr Hug was awesome and made sure I knew everything i needed to know before check in
The owner was great to work with Would definitely visit this location again
Beautiful home spacious close to attractions Will definitely stay there again
The complex is guarded and seems a very nice safe place
It's on a great community and not far from anything
It is in a great location within the development and close to all the Disney attractions
Perfect house in a great area Close to everything you want to do when in Orlando 10/10
There is a large supermarket a few minutes away
Read more reviews

5. Terra Verde Resort (from USD 116)

Terra Verde Resort features not only beautiful properties for rent but also popular amenities such as a heated pool, fitness center, theater room, playground, tiki bar, barbecue grill, and a fishing lake. The private spa facility enables the guests to rejuvenate and refresh from the stress of daily life. The guests can be mesmerized by the sunset views from the master bedroom of this resort. Each guest is provided with a private code to access their rooms during the stay. High-speed internet access is available at the gated luxury resort.

Stayed at this property?
Kissimmee, Florida, United States
6.42 km (4.0 mi) from Kissimmee Lakefront Park
PRIVATE VACATION HOME 8 Guests 3 Bedrooms 3 Bathrooms

Top guest reviews
Amenities & Room:
The beds were comfortable and it looked like
The fact that linens were provided was an added bonus
it was wonderful to come home each night to a clean safe home
The beds were very comfortable
Well maintained home and amenities as depicted in photos Kevin P
Townhouse was very clean and nicely decorated
The townhouse was exactly as promised in the listing very clean and had everything we needed
your stay was spotlessly clean and home tastefully decorated neighbourhood quiet and very secure as gated community
The house was recently renovated and everything was nice and fresh
and she got back to me quickly
The owner was very attentive communicating with us throughout the process
Home was clean nice having a hot tub right out the back door along with all the perks Terra Verde offered
I had a question about the thermostat and messaged the owner
washer dryer grill
LOL)The house is close to shops and other stores and it was not far from the parks Because the little ones get too tired
Overall great gated community easy access to Parks
It was a great location with lots to do nearby (natural springs Chocolate Kingdom restaurants and parks) and the pool to relax in back on property or
The location to the Terra Verde Clubhouse is so close and walkable
Expect about a 22-25 min drive each day into the parks because of morning traffic
Read more reviews

6. Jenny’s studio

Staying in Jenny’s studio has so many advantages. This house vacation rental has close vicinity to the Kissimmee attractions, including the Walt Disney World. It also offers a comfortable stay in the middle of the serene surroundings. Located just a 15-minute drive from the nearest airport and a 25-minute drive to the theme parks, this Florida vacation home offers a fun-filled escape. The house includes a kitchenette with a fridge, coffee maker, and microwave which makes it ideal for families. Wi-Fi, an iron, a heating facility, hot water, free parking, and a smart lock are the facilities offered in the house. In addition to this, a delicious breakfast is served to the guests.

Stayed at this property?
Kissimmee, Florida, United States
5.63 km (3.5 mi) from Kissimmee Lakefront Park
151 reviews  
Entire guest suite 1 Bed 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
also the apartment was stocked full of amenities like coffee and even netflix
clean towels soft bed nice tv coffee couch big shower
the bed was comfortable and the tv was easy to navigate and had access to most streaming services
we had a great stay in this apartment
the bathroom is beautiful
very clean and tidy
super clean and nice place
iris place was very clean and cozy
it is very clean and nice decor
studio apartment sparkling clean and comfortable
easy to find and easy to communicate with owner through email
all within budget iris was very accommodating had a great response time and made local recommendations available in advance
iris is a great and supportive host
iris was a great host i enjoyed the stay so much i will book her place again
host responded fast and was on location within minutes when asked for help
close to the airport and attractions
good location and neat place
close to stores restaurants and attractions
good location to where we wanted to be
we enjoyed the location
Read more reviews

7. Private studio with independent entrance

The Lilac House is a beautifully maintained vacation rental with attractive amenities. The accommodation can sleep two guests in their one bedroom with one bathroom. Located close to Walt Disney World and several restaurants, shopping areas, old town, and downtown Kissimmee, this vacation home offers a relaxing retreat to the occupants. The room looks like a private studio with a work desk, TV, ironing facility, Wi-Fi access, air conditioner, central heating, coffee maker, microwave, and refrigerator. A luggage storage facility is also offered to the guests.

Stayed at this property?
Kissimmee, Florida, United States
2.75 km (1.8 mi) from Kissimmee Lakefront Park
121 reviews  
Entire guest suite 2 Beds 1 Bedroom 1 Bathroom

8. Family-friendly home

Step inside this spacious home which is perfect for group and family vacations. The house is located within a 20 to 25-minute drive to Universal Studios, Disney World, and International Drive. Set within a few minutes from the major shopping areas of Kissimmee, the home is ideal for taking a stroll in the streets of Kissimmee. This clean and safe vacation rental can ensure a peaceful holiday for the guests. A laundry facility is offered in the large garage of the house. A TV, an iron, a dryer, toilet essentials, an air conditioner, a heating facility, parking, and a pool are available in the house. A kitchen with basic facilities can be used by the guests of this family-friendly house.

Stayed at this property?
Kissimmee, Florida, United States
7.91 km (5.0 mi) from Kissimmee Lakefront Park
90 reviews  
Entire house 4 Beds 3 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
the beds were really excellent we loved the couch outside
pool furniture was high quality sturdy and comfortable
provided extras like air fresheners shower gels towels and toilet roll which helped us out a lot
all beds were super comfortable
the master suite was large with large closets nice shower and overlooked the amazing pool
very clean and nice neighborhood
chris's house is clean nice and comfortable
the house is beautiful and very clean and very relaxing
the house was very clean and also very big
the house was very clean and the neighborhood was very quiet
owner was very responsive
very quick and helpful responses
very responsive and attentive to questions
chris was a great host with quick responses to all communication
great and cozy place quick responses which were really helpful
good location only short distance from airport
great location for a family vacation
perfect location for all the theme parks
i would definitely recommend chris’ place to anyone looking for a cozy location in lake nona
great location and very responsive hosts
Read more reviews

A fun-filled vacation at Kissimmee

Discover the joy of traveling by exploring the beautiful city of Kissimmee. Take your pick from this collection of vacation rentals and enjoy the most memorable vacation ever.

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.


Get Trip101 in your inbox

Unsubscribe in one click. See our Privacy Policy for more information on how we use your data

Hemasudha is a dedicated travel writer whose true passion lies in exploring the world. Traveling, for her, is not just a hobby but a profound spiritual experience that she is deeply passionate...Read more

 Want to contribute as a Local Expert?
Explore Kissimmee
Good things are meant to be shared!
Back to top
Visited any of these places? Click this button to activate our "Add a Tip" feature to share your experience.