Located in Central Florida, Kissimmee is quite a popular home base for those who want to explore Orlando’s many theme parks and attractions. Kissimmee is situated just 22 mi (35 km) from Orlando and around 12 mi (19 km) from Walt Disney World Resort. Just close by are Universal Orlando Resort, SeaWorld Orlando, LEGOLAND Florida Resort, and Fun Spot America. Outdoor lovers will find plenty of adventures while staying in Kissimmee. Lake Tohopekaliga lies a short drive away and provides a wide range of water sports worth trying. Paddling Center at Shingle Creek and Kissimmee Lakefront Park are other fantastic places within the city that visitors can check out. For shopping and dining, the entertainment districts of Old Town and Disney Springs are great stops. Planning a trip and wondering where to stay? Read on for a curated list of the best Airbnbs with pool in Kissimmee, Florida.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to pool. The image galleries get refreshed with the latest updates regularly. They were last updated on April 12, 2024.
1. Five-bedroom house for large group
This house is located within a gated community and in front of a lake. It offers five bedrooms that can together host up to ten guests. Additionally, the house offers a large open-concept common area with a living room, a fully stocked kitchen, and a formal dining table. A game room provided with PS4 and Wii is also available.
The enclosed patio overlooks the lake and features a pool with a large deck. This part of the property also comes with outside dining facilities and lounge chairs. The rental fee includes access to community facilities, such as the fitness centre and resort swimming pool.
Kissimmee, Florida, United States
5.98 km (3.8 mi) from Main Gate Flea MarketSuperhost
Accommodates: 10
Top guest reviews
Amenities & Room:
beautiful house nice pool & great grillkids loved the swimming pool would definitely stay againwarm pool perfect size houseCleanliness:
house was very clean and neatgreat place nice and cleanclean and very nice you will lovegreat house clean and great locationthe house was super clean modern and bed super comfortableHost:
pascal was a wonderful hostpascal was a great host very attentivehost is easy to talk topascal is a wonderful host very quick to answer any and all questionsperfect getaway pascal is a great hostRead more reviewsLocation:
beautiful home and great location close to everythinggreat place to stay close to all highwaysthe location was in close proximity to the amusement parks we visitedfantastic house - loved the pool and the location right by a walking trailloved the walking path behind the house
2. Welcoming townhouse with patio
This two-level townhouse is a great option for up to nine guests. The house includes four bedrooms, a spacious open-concept living area, and a well-equipped kitchen. The living room on the ground floor leads to a patio that comes with a splash pool, a barbeque station, and lounge chairs. Guests can enjoy pool heating and access to the barbeque equipment for an additional fee.
WiFi is also available for those who need to stay connected online.
Kissimmee, Florida, United States
5.76 km (3.6 mi) from Main Gate Flea MarketAccommodates: 9
Top guest reviews
Amenities & Room:
the fan in the bathroom was not working eitherthe house comfortably fit my entire family and we really enjoyed the grill and poolit was decorated nice and my children loved the heated poolafter a long a day of walking it was comforting to jump into a well-maintained and heated poolCleanliness:
very clean & cozyplace is clean snd newgreat place clean & spacioussuper clean house diego was also very communicative during the whole processthe place is spotless and very well decoratedHost:
very fast responses very helpfulhe’s truly a great hostthanks diego for being a great hostdiego was a wonderful hosthad a great time diego was the perfect hostRead more reviewsLocation:
a great place and locationdiego’s place is literally perfect and everything is close byeveryone loved the place and the location is really goodthe location was very convenient and the house was beyond amazinggreat location easy access to parks restaurants and bars
3. Attractive villa with spa (from USD 194)
With its modern-style interiors and top-end amenities, this house located inside a gated community offers a plush setting. It provides four bedrooms and can host up to nine guests. Other features of the house include a living room and a fully equipped kitchen.
The rental provides a private 30 ft (9 m) by 12 ft (3.6 m) pool with a deck and a covered lanai set up with dining facilities. The pool area also comes with a jetted spa that can hold up to eight persons. Pool heating is provided at an additional charge per day. Additionally, the house is around 9 mi (14.5 km) from Walt Disney World and Universal Studios.
Kissimmee, Florida, United States
6.08 km (3.8 mi) from Main Gate Flea MarketAccommodates: 8
Top guest reviews
Amenities & Room:
the pool overlooking a huge oak tree and a lakelovely house very spacious loved the pool very comfortable would rent againgreat pool with a simple house and a bunch of bedroomsCleanliness:
very clean and up to datethe house is wonderful and very clean and spaciousvery nice and clean housethe villa was clean spacious and relaxingthe house is stylish and cleanHost:
the host is kind and very responsiveeric was a great hostawesome host and great spot to staywe went for a family vacation and eric was such a great hosthe was responsive and very thoroughRead more reviewsLocation:
the location is ideal to attraction parks and dining/shoppinggreat place and definitely a convenient locationvery clean great location walmart is only 4 min awaya great place to stay very nice and perfect distance from disney world and universal studiosyou can't go wrong with this house perfect place to stay
4. Modern house with access to gym (from USD 121)
This newly built house exudes a sleek, contemporary vibe with elegant furnishings in pleasing neutral colours. It offers four bedrooms that can host up to ten guests. Spread over two levels, the house provides an open-plan living area that includes a full kitchen and a dining table. Meanwhile, the upper level features bedrooms.
At the rear of the house, a private pool with a small deck is available. Heating for the pool and barbeque equipment can be arranged for extra fees. An attached garage is an added convenience. Additionally, guests can access shared facilities, such as a gym.
Kissimmee, Florida, United States
5.62 km (3.5 mi) from Main Gate Flea MarketAccommodates: 10
Top guest reviews
Amenities & Room:
amazing space super comfortable and relaxingthe pool was just perfect for my 5 and 1 year oldthe pool was great for my 2 and 6 years oldCleanliness:
everything was very clean and well sanitizedsafe clean and spaciousthe condo is very clean and looks exactly like pictureswas a great stay and very cleanwhen staying somewhere other than my house my number one priority is cleanliness and the house was cleanHost:
gustavo was a very nice hostgustavo was a great hostgustavo was a great hostgustavo was a great host he was quick with anything i needed a response toogustavo is a great hostRead more reviewsLocation:
the location was perfectamazing house and great locationgreat location; walking distance to wal-mart and wawabeautiful home convenient location in a nice quiet communityit was a pretty central location in kissimmee too everything was perfect
5. Neat property close to shopping centre
This house is located within a gated community, guaranteeing you are safe and secure. The house provides four bedrooms, an open-plan living area that includes a full kitchen, and a game room. At the back, a private pool with a small deck is available. Heating for the pool is available on request and for an extra charge.
Guests can enjoy community facilities, such as the clubhouse, outdoor resort-style pool, and gym. In terms of location, the community is within minutes of The Loop, a shopping centre in the city.
Kissimmee, Florida, United States
6.14 km (3.9 mi) from Main Gate Flea MarketAccommodates: 10
Top guest reviews
Cleanliness:
house was clean and organize when we arrivedpool was clean and ready to jump inthe house is as advertised super clean and easy access to the parksHost:
best location and the host is very goodRead more reviewsLocation:
it’s in a great location convenient to lots of shopping and isn’t far from walt disney worldwould definitely book again close to disney and universal
6. Upscale abode for 15 people (from USD 296)
Expansive and beautifully appointed, this house provides six bedrooms that can host up to fifteen guests, making it ideal for large groups. The house incorporates a spacious common area that includes a trendy living room, a full kitchen that features a large island counter, and a formal dining area. Additional amenities include a movie theatre and a game room.
Guests can enjoy a sprawling back patio at the rear of the house that offers a private pool and a hot tub. The adjoining deck provides lounge chairs and alfresco dining facilities. Heating for the pool and the spa can be arranged separately with payment of extra charges.
Kissimmee, Florida, United States
6.12 km (3.8 mi) from Main Gate Flea MarketAccommodates: 15
Top guest reviews
Amenities & Room:
all of the rooms were a good size and we had plenty of space to spread outit was fun looking in every room for all the detailsthe laundry room was a nice size & the washer and dryer were kept in good shapethis house is amazing there’s so much room to spread outCleanliness:
it's huge and clean and so stylishoverall the entire place was clean and had plenty of tvshis place is clean well designed and spacioussuper clean and has any amenity you might needeverything is close by very beautiful home for huge family like mine very clean and organized homeHost:
amazing property and amazing hostthe host is very kind and responds very quicklybeautiful home and wonderful hostexcellent place wonderful hosts and definitely recommenddiego was an amazing hostRead more reviewsLocation:
wonderful house close to disneythe location was great alsoperfect location to disney universal shops and restaurantsgreat place to stay for an orlando vacationeasy drive to all the parks and quick to get to the grocery store
7. Cheerful and inviting accommodation
Featuring bright decor, this stylish two-level home offers five bedrooms that can sleep up to ten guests. The ground level features an open-plan living area that encompasses a sitting area, a full kitchen, and a dedicated dining space. The upper level is where you will find the bedrooms.
A pool surrounded by lounge furniture is available. The house is located within a quiet residential community that is around 20 minutes from Orlando’s major attractions.
Kissimmee, Florida, United States
14.37 km (9.0 mi) from Main Gate Flea MarketAccommodates: 10
Top guest reviews
Cleanliness:
the house is extremely clean and the pool in the back was an amazing featuregorgeous home to stay in super clean and spacioussuper modern spotless convenient and worth every single dollar we spentHost:
jaime is very responsive and active what a great host thank you again we loved itRead more reviewsLocation:
location was great with grocery and conveniences stores everywherethis place is a perfect locationclose enough from the parks and in a quiet and nice neighborhood
8. Spacious townhouse with WiFi (from USD 137)
This townhouse is located inside the gated community of Storey Lake Resort and can accommodate up to 10 persons. It offers four bedrooms, an open-plan living area, and a fully stocked kitchen. The house provides a back patio that features a pool and a deck with lounge chairs. Heating the pool is an additional service that attracts an additional charge. WiFi is available, as well.
As a part of the rental fee, guests are free to access the clubhouse that offers a swimming pool with a lazy river and splash pad. Other common facilities guests can use include a fitness centre and sports facilities.
Kissimmee, Florida, United States
2.76 km (1.8 mi) from Main Gate Flea MarketAccommodates: 10
Top guest reviews
Amenities & Room:
be prepared to buy a few household items like garbage bags toilet tissue hand soap and dish soapthe kitchen is fully stocked and well appointedCleanliness:
the bathrooms were clean the beds were clean towels were cleanit was super clean and spaciousplace was very cleanthe house was extremely clean (a strong cleaning chemical smell overpowered us upon arrival but dissipated quicklyvery clean beautiful set up overall a great placeHost:
i contacted the host twice during my stay and they were amazingthe kind size bed on main level has a very cozy bed super soft mattressRead more reviewsLocation:
place was great located near pleanty of shopping centers restaurants and close to all the major amusement parksfamily fun resort comfortable accommodations location is excellentclose to stores restaurants and the many orlando attractionsthe location is fantastic and accessing the house in this gated community couldn't be easierthe location is awesome only about 20 mins to disney
9. Four-bedroom home with laundry facilities
Set within the gated community of Bella Vida Resort, this property offers a tasteful setting with a private pool. Inside, you will find a graceful open-plan living area that overlooks a garden and features a sitting area, a full kitchen with a dining counter, and a dining section. If you want to have your pool heated, there will be an additional fee per day. If you are planning a long-term stay, a washer and a dryer are available.
Guests are free to make use of the common facilities inside the community, including a picnic area and clubhouse.
5.16 km (3.3 mi) from Main Gate Flea MarketAccommodates: 12
Top guest reviews
Cleanliness:
very clean and excellent staythis place was amazing very clean and stylishvery clean and house owner is very responsive and helpfulRead more reviewsLocation:
very beautiful house in a perfect location near disney great for big groupswithin minutes of shops grocery stores mall and attractionsdanielle was super accommodating the house is in a great location
10. Two-level home with kitchen
With five bedrooms, this two-level house can host up to thirteen guests. The property’s open living room feels expansive and bright thanks to its high ceiling and multiple windows. Aside from a large living room, this house has a modern kitchen with a breakfast counter and a separate dining section.
The rear of the house boasts a pool with a deck fitted out with patio furniture and barbeque equipment. The heating of the pool and use of the barbeque equipment attracts additional fees.
Kissimmee, Florida, United States
10.45 km (6.5 mi) from Main Gate Flea MarketAccommodates: 13
Top guest reviews
Amenities & Room:
wish we would have had time to check out the amenities at the new community pool areakids too enjoyed great in the multiple poolsspacious and plenty of room for our 7-adult partylots of good room for the visitorsthe rooms were gorgeousCleanliness:
clean comfortable and stylishamazing house very clean and beautifulbeautiful home house was cleanrental was clean and spacious just as describedvery spacious and cleanHost:
vhc was very responsive and helpful before and during our staybeautiful spacious home with great communication from the hostRead more reviewsLocation:
the location was goodlocation is great close to shops and restaurantsperfect location to disney shopping and restaurantsfabulous location spacious and comfortablegood luck if you choose this place
Relax and unwind during your trip
This article provides a list of wonderful rentals that offer access to pools, which will make your trip even more fun. Find the perfect option for your needs from these best Airbnbs with pool in Kissimmee, Florida.
History
Get Trip101 in your inbox
Unsubscribe in one click. See our Privacy Policy for more information on how we use your data
Create an account to