
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.

Game Room/HeatedPool/Piano Upscale Waterfront Home
Welcome to one-of-a-kind upscale contemporary waterfront oasis, where luxury meets comfort. This stunning house is nestled in a tranquil neighborhood, just moments away from the airport and all the attractions you desire. Step inside to find a beautifully renovated space: fully equipped open kitchen, game room, gym, pool table, grand piano etc Outside: private screened in heated pool($20/night heating fee)with breathtaking waterviews, patio equipped with grill, dining table, ping pong and more!

3121-402 Resort Lake View Disney Universal Orlando
Minutes from Disney World Orlando Florida, Modern & Stylish 2bed/2bath fully equipped apartment for up to 7 guests, located in the family friendly Storey Lake Resort. FREE Clubhouse & WATERPARK amenities: Heated Pool, Hot Tub, Kids Splash Zone, Water Slides, Lazy River, Gym, Tiki Bar, Ice Cream Shop & more. The apt is located: 10 min drive to DISNEY, 25 min to UNIVERSAL STUDIOS, 18 min to SEA WORLD. FREE Parking. FREE Waterpark. No extra FEES. Gated Resort with Security 24/7 & Self check-in!

Roomy 2br w/ jacuzzi close to Disney
This townhouse provides a open main living space that allows you to connect the dining and a fully equipped kitchen. The house can accommodate up to 6 guests, divided into one luxe king en-suite, and a design theme two full en-suite. Relax in your own private spa after a long day at the parks. Clubhouse with a gym, amazing heated pool, pool bar, a restaurant and only 5 min from Disney and golfing area. Parking, wifi ,resort’s amenities are free Close to lakes, camping, beach, vineyards, farms

⁕ Disney parks! Luxury resort villa • Private pool
This sunny single-story home has 4 beautiful bedrooms, 2 full bathrooms, new AC system, fully stocked kitchen, and private screened freshwater pool. Perfect for families or groups, it accommodates up to 8 guests. Just minutes from DisneyWorld, Universal Studios, SeaWorld, Legoland, and Orlando’s top attractions. Conveniently located close to restaurants and shopping, this non-smoking house is nestled in a peaceful and secure resort, offering all the comforts of a "home away from home" vacation.

Cozy Disney Oasis Pool Home 10 Mins from Parks!
Our charming, pet-friendly home is located in the prime area of Kissimmee, Florida. Your family will be close to Disney parks, restaurants, Old Town, and Downtown Disney. Just bring your bag—we have everything you need! Settle into our fully equipped home, thoughtfully designed to create lasting memories with family and friends. Enjoy the Florida weather by cooling off in our open-air pool or grilling by the poolside lounges. Relax in our airy bedrooms, including Mickey and Minnie themed rooms!

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.

Luxury Villa! /Game Room/ Pool Heater
Luxury Villa on a gated community in Kissimmee (Four Corners). Modern. Situated 10 min. from Disney theme parks. Well decorated and presented. Game Room, Mini Gym, Beautiful, large pool deck which is totally enclosed and secluded. There is a private Pool and Spa. Three Bedrooms and Bedroom one is separate from the main house but still enclosed in the building. This would be ideal for a young couple within the group as it has its own bathroom, small kitchen and also total privacy.

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.

Luxury Encore Pool Spa Pets Game Rm Theater Gym
Amazing Brand New Modern Luxurious Home at Encore Resort Reunion. PET-FRIENDLY & Minutes to all Theme Parks. BRAND NEW HOME. Private Pool & Spa / Game Room / Movie Theater / Gym / Massage Chair / Fireplace / PS5 / Board Games & Much More. Embrace the extraordinary and book your stay at our home, where luxury, entertainment come together for an unforgettable vacation experience. ** Please review the rules before booking. Waterpark access is not included. **

Sleek Modern Gateway 10 Min to Parks Pets Allowed
Welcome to Your Magical Gateway – Just 10 Minutes from Orlando's Magical Parks! Location: Perfectly located for Disney and Universal, our apartment offers a peaceful retreat with all the comforts of home. Whether you’re here to explore the magic unwind, or even stay for longer terms, you’ll love every moment of our cozy space. The property sleeps 4 people! PLEASE CONTACT US TO INQUIRY ABOUT ADDITIONAL POTENTIAL DISCOUNTS FOR MULTIPLE DAYS STAY

Disney Area| Private Pool| Resort Waterpark 2956
Minutes from Disney, this spacious 4-bedroom townhome is located in the sought-after Storey Lake Resort. Relax in your private screened pool after a day at the parks and enjoy access to amazing resort amenities including water slides, lazy river, clubhouse, fitness center and kayak rentals. Comfortably sleeps up to 12 guests with a full kitchen, fast WiFi and free parking. Perfect for families visiting Disney and Orlando attractions.
Popular amenities for Kissimmee rentals with a pool
House rentals with a pool

4BR Disney & Universal Themed Villa Reunion Resort

Pet-Friendly Pool Home Near Orlando

The Ultimate Disney Experience PLUS MORE!

Disney Orlando vacation home with private pool 4

Near Disney 5bed home with pool and game room

VillaLumine•PrvtPool•Heater•Aesthetic•NearDisney

View the Disney fireworks from your pool!

Stunning 6BR Lakeview @Storey Lake | Disney - 2929
Apartment rentals with a pool

Perfect for Two Families • Sleeps 8 • Top Location

Stylish Condo 20 mins to Disney/King Bed

Marriott Sabal Palms 2BD Villa

The thrill of luxurious living just 15 min/Disney!

Lovely ❤️ Beach style Apt near Disney & Universal

202_Magical and Cozy 2BR minutes from Disney

Private Rooftop Suite! No resort fees!

Cozy Condo at Secret Lake near Disney
Other holiday rentals with a pool

Casa localizada a 10 minutos dos parques.

Rare-find! 5-Star Spotless 3/3 home near Disney!

2 bedroom Balcony King Suite - Lake & Pool view

!NEW! Family Pool Home Near Disney Orlando

Stunning Storey Lake Resort near Disney

Home, Private Pool, 10 min to Disney, 3 BR/2 Baths

Disney Getaway, Hot Tub, 10 min to Parks, 6 people

Luxury 4 Bedroom Home - Resort Access! Disney!
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £108 | £110 | £115 | £113 | £99 | £105 | £111 | £97 | £90 | £95 | £107 | £126 |
| 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 £15 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
- Rentals with a fireplace Kissimmee
- Lakehouse rentals Kissimmee
- Serviced apartment rentals Kissimmee
- Mansion rentals Kissimmee
- Fitness-friendly rentals Kissimmee
- Rentals with a cinema Kissimmee
- Waterfront rentals Kissimmee
- Private suite rentals Kissimmee
- Apartment rentals Kissimmee
- Pet-friendly rentals Kissimmee
- Beachfront rentals Kissimmee
- Cottage rentals Kissimmee
- Rentals with breakfast Kissimmee
- Family-friendly rentals Kissimmee
- Holiday home rentals Kissimmee
- Rentals with a sauna Kissimmee
- Rentals with outdoor seating Kissimmee
- Villa rentals Kissimmee
- Rentals with an accessible-height toilet Kissimmee
- Rentals with a firepit Kissimmee
- Townhouse rentals Kissimmee
- Rentals with a hot tub Kissimmee
- Tiny house rentals Kissimmee
- Rentals with lake access Kissimmee
- Beach house rentals Kissimmee
- Rentals with an accessible-height bed Kissimmee
- Rentals with an EV charger Kissimmee
- Resort rentals Kissimmee
- Hotel rooms Kissimmee
- Rentals with a washing machine and dryer Kissimmee
- House rentals Kissimmee
- Rentals with a patio Kissimmee
- Smoking-friendly rentals Kissimmee
- Ski-in/ski-out rentals Kissimmee
- Guest house rentals Kissimmee
- Flat rentals Kissimmee
- Rentals with a kayak Kissimmee
- Rentals with beach access Kissimmee
- Cabin rentals Kissimmee
- Rentals with pools Osceola County
- Rentals with pools Florida
- Rentals with pools United States
- Walt Disney World Resort
- Universal Studios Florida
- Universal Orlando Resort
- Orange County Convention Center
- Walt Disney World Resort Golf
- Disney Springs
- Magic Kingdom Park
- SeaWorld Orlando
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Discovery Cove
- ESPN Wide World of Sports
- 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
- ChampionsGate Golf Club






