
Holiday rentals with a pool in Kissimmee
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Kissimmee
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Gorgeous 5BR PetFriendly @Encore Near Disney 7693
Modern, stylish, and luxurious, 3000sf home, with 5 bedrooms, at the world's renowned Encore Resort at Reunion. It features a game room, a huge backyard, an oversized private pool, spa. A true dream vacation home. 6 Minutes away from Super Walmart and Publix supermarket 15 Minutes away from Disney Parks 15 minutes away from Disney Springs 15 Minutes away from Premium Outlets 20 Minutes away from Universal Studios 20 Minutes away from International Drive attractions *PLEASE MAKE SURE TO READ THE

5BR Mario& Princess Peach•Pool•Theater•Free Resort
Escape to an unforgettable Disney Adventure, just 9 miles from Walt Disney World! Perfect for Mario Bros, Moana & Princess Peach fans. Enjoy themed rooms, cozy bedding, and a private pool. Indulge in movie nights in our Mario Bros theater! Bring the whole family, including pets, and make magical memories. 9 miles to Walt Disney World 🎢 16 miles to Sea World 19 miles to Universal 27 miles to MCO (Orlando International Airport) Join Us for an Unforgettable Disney Adventure! Learn More Below!

Disney Oasis with Private Pool and Game Room
Beautiful lakeside home with a private south facing pool in a gated community 12 miles from Disney. Enjoy fishing in the lake in the backyard. Game room with pool table, skeet ball, foosball table and a gaming system with hundreds of old favorites like Pac Man and Mario Brothers. 4 bedrooms and 3 bathrooms. Fully equipped kitchen and an outdoor grill makes preparing meals a breeze. Flat screen TVs in all 4 bedrooms and living room. We also have beach chairs, cooler and other beach equipment.

Tahiti Gil’s Mananui: Disney Poly & Tiki Inspired!
Aloha Adventurers! Welcome to Faré Mananui. Your passport to a far away tropical hideaway awaits, so get ready to grab your favorite Aloha shirt! Mananui was made for the Disney/Tiki ADULT in mind! Imagined by artist @TahitiGil & designed by @TyphoonTommy (Former Disney/Universal creative team & designer of the Suffering Bastard Tiki Bar in Sanford, Fl. Experience your next Adventureland/ Enchanted Tiki Room “story dwelling” adventure from the moment you step thru the door! - Kungaloosh!!

Villa Resort Club
VILLA LUJOSA - BARRIO SÚPER HERMOSO POOL HEATER HOUSE - Diviértete con toda la familia en este alojamiento con estilo moderno , te encantará el área de picnic frente de la casa , el área de juegos y piscina con calentador , un espacioso lugar de hierba artificial para jugar tus niños y en una zona muy trankila cerca de los parques de Disney y del aereopuerto MCO . TE ENCANTARÁ LA CASA Local utility or county personnel may access exterior areas for maintenance without prior notice.

Waterfront Condo minutes to Disney & Universal
Just minutes from Disney World and Universal Studios, this condo places you in the heart of Orlando’s top attractions, including Disney Springs, Islands of Adventure, SeaWorld, Magic Kingdom, Epcot, two outlet malls, and more. Relax on your private balcony with breathtaking views of Lake Bryan, or enjoy the resort-style pool with a full Tiki bar and dining menu. Additional perks include free parking, 24-hour security, and complimentary HBO & Netflix. No deposit required and no extra fees.

*Modern Luxury Reunion Oasis | Pool, Spa & Cinema
Wow-factor luxury meets unforgettable family fun, just minutes to Disney, at this show-stopping home in the exclusive Reunion Resort. Step outside to a massive 2,400-sq-ft southwest-facing pool deck with outdoor kitchen, private pool, overflow spa, and no rear neighbors—perfect for all-day sun and sunset swims. Inside: private movie theater, billiards game room, and spectacular Star Wars & Frozen II theme bedrooms with tube slide, plus Xbox and PlayStation for nonstop entertainment.

Top1% *La Piu Belle* Retreat at Storey Lake View
Welcome to **La Piu Belle Retreat** – a stylish, sunny, and serene escape at Storey Lake Resort. This 2-bedroom condo features boho-chic decor, a fully equipped kitchen, a bright balcony, and cozy vibes throughout. Enjoy access to a water park, gym, and more. Perfectly located just minutes from Disney, premium outlets, and top restaurants. Excellent Reviews: Our guests rave about their experiences, highlighting our cleanliness, location, and exceptional service.

Spacious 2BR Apt in Resort 10 min from Disney
Featuring comfortable, family-friendly amenities, this property provides relaxation in a peaceful, wooded setting while being close to all the major area theme parks. Enjoy the outdoor swimming pool or stay active at the fitness center and tennis courts. Families will appreciate the playground and children's pool. Additional conveniences such as a bar, free Wi-Fi, and free parking ensure this property is your home away from home near Orlando's famous theme parks.

Waterfront Wizarding Near Universal's Harry Potter
This spellbound stay, situated in the prestigious Lake Berkley Resort, boasts lake views & private pool. With 6 bedrooms, 3 bathrooms, well equipped kitchen & comfy living spaces, this thematic home is ideal for families & friends seeking an immersive vacation. A 10min drive to Disney, 15min to Sea World & 20min to Universal's Wizarding World of Harry Potter, this magical manor provides a convenient home base for exploring Orlando's famous attractions.

4420 Le Reve 4BDRM townhouse close to Disney
Our townhouse can accommodate up to 10 people, with 4 bedrooms and 3.5 bathrooms and has a small jacuzzi for you to relax after a long day at the parks or outlets. Our property is only 10 miles to Disney’s theme parks and 15 miles to Universal Studio and major Outlets. It has many restaurants and supermarkets (Walmart, Target, Sam’s Club) nearby. Walmart Superstore is just 0.2 miles or 5 minutes walk.

8615 Vacation Oasis House Private Pool Grill
Relax with the whole family at this peaceful PRIVATE POOL & GRILL house in Kissimmee, just minutes from Disney Parks and Margarita Ville Water Park. Master Suite has a great view to Pool & BBQ outdoor area. 3 bedrooms, 2 bathrooms, fully equipped kitchen, 2 car garage, 3 Smart TV's and strong Wi-Fi all around the house. Enjoy and have unforgettable moments at our BBQ area next to our private pool.
Popular amenities for Kissimmee rentals with a pool
House rentals with a pool

Disney Orlando vacation home with private pool 4

*Luxe Disney Home* Priv Pool/Spa- 6BR Sleeps 15

Near Disney 5bed home with pool and game room

Luxury Home w/ Pool & 6 Beds near Disney

Kissimmee

7839 6BD Beautiful Family Home in Reunion Resort

Dream House with Private Pool Close to Disney 2470

2602SN - Stunning Home 5 Ensuites Near Disney
Apartment rentals with a pool

Perfect for Two Families • Sleeps 8 • Top Location

Stylish Condo 20 mins to Disney/King Bed

A luxurious living just 15 min/Disney!

Penthouse Lakeview Minutes to Disney/ Universal

Disney Oasis by the lake

Cozy Condo at Secret Lake near Disney

Modern Condo with Lake View Near Disney 3151

Disney Retreat
Other holiday rentals with a pool

2588-Stunning Themed-House at Storey Lake

Stunning Storey Lake Resort near Disney

Top Tier Reunion Resort 7 Bed Private Hot Tub Pool

Tropical Oasis Near Disney

Luxury 5BR Villa with Private Pool + Water Park

Villa w/ Pvt Pool & BBQ + Games | 15 min Disney

Luxury Mario Bros. Townhome Near DisneyWorld Parks

Le Reve Town House
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $196 SGD | $205 SGD | $219 SGD | $195 SGD | $170 SGD | $182 SGD | $191 SGD | $168 SGD | $155 SGD | $164 SGD | $184 SGD | $218 SGD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
Quick stats about holiday rentals with a pool in Kissimmee

Total holiday rentals
Explore 6,460 holiday rentals in Kissimmee

Nightly prices starting at
Kissimmee holiday rentals start at $25 SGD per night before taxes and fees

Verified guest reviews
Over 243,320 verified reviews to help you choose

Family-friendly holiday rentals
5,500 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 1,020 rentals that welcome pets

Rentals with dedicated workspaces
3,560 properties have a dedicated workspace

Wifi availability
6,400 of Kissimmee holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Kissimmee rentals

4.7 Average rating
Kissimmee stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- St Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Tampa Holiday rentals
- Four Corners Holiday rentals
- Key West Holiday rentals
- Tampa Bay Holiday rentals
- Hotel rooms Kissimmee
- Rentals with breakfast Kissimmee
- Guest house rentals Kissimmee
- Waterfront rentals Kissimmee
- Beach house rentals Kissimmee
- Cottage rentals Kissimmee
- Rentals with a kayak Kissimmee
- Rentals with a sauna Kissimmee
- Rentals with a fireplace Kissimmee
- Private suite rentals Kissimmee
- Resort rentals Kissimmee
- Rentals with a patio Kissimmee
- Smoking-friendly rentals Kissimmee
- Rentals with an accessible-height toilet Kissimmee
- Villa rentals Kissimmee
- Rentals with outdoor seating Kissimmee
- House rentals Kissimmee
- Rentals with a hot tub Kissimmee
- Family-friendly rentals Kissimmee
- Fitness-friendly rentals Kissimmee
- Rentals with a cinema Kissimmee
- Beachfront rentals Kissimmee
- Rentals with lake access Kissimmee
- Holiday home rentals Kissimmee
- Flat rentals Kissimmee
- Ski-in/ski-out rentals Kissimmee
- Rentals with beach access Kissimmee
- Mansion rentals Kissimmee
- Rentals with an EV charger Kissimmee
- Lakehouse rentals Kissimmee
- Rentals with an accessible-height bed Kissimmee
- Serviced apartment rentals Kissimmee
- Apartment rentals Kissimmee
- Rentals with a firepit Kissimmee
- Townhouse rentals Kissimmee
- Pet-friendly rentals Kissimmee
- Tiny house rentals Kissimmee
- Rentals with a washing machine and dryer Kissimmee
- Cabin rentals Kissimmee
- Rentals with pools Osceola County
- Rentals with pools Florida
- Rentals with pools United States
- Universal Studios Florida
- Walt Disney World Resort
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Orange County Convention Center
- Disney Springs
- SeaWorld Orlando
- Universal's Volcano Bay
- Magic Kingdom Park
- Orlando / Kissimmee KOA
- Discovery Cove
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Camping World Stadium
- Aquatica
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- Southern Dunes Golf and Country Club
- University of Central Florida
- ChampionsGate Golf Club







