
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.

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.

Mad Men Magic Kingdom House*FAB POOL*OutdoorMOVIE
AMAZING Pool Deck Extension cira 2023! Its the BIGGEST pool deck at the resort! Plus JAW DROPPING, Fancy, Fun, Fountain Jets w/ LED lighting, high-end glass tile & a Mickey Mosaic giving you an ULTIMATE luxury pool experience. This SALT WATER POOL/SPA will leave your skin feeling soft w/ no eye-sting & it has botanical qualities for your muscles after long days at the parks! Enjoy all this plus our unique OUTDOOR MOVIE EXPERIENCE & FIRE-PIT for the BEST vacay ever only 6 miles to Disney!

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.

Windsor Orlando Private Arcades,Theater,Pool-Spa
Orlando, Disney, Arcade, Movie Theater, Massage Chair, Pool, Hot Tub, 2 King Beds, Kids Bunk Bed, Kissimmee. Upgraded games room IN the private home, theater for evenings home and your private lanai with pool and hot tub. Choose from including Pump It Up dance, Sponge Bob Racing, NASCAR racing, Legends 3, Pac-Man's Arcade Party, an 80-inch TV, and an Xbox 360. Watch your favorite movies on the 92-Inch projection screen, surround sound, and stadium style seating.

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. **

Modern 4bdr Storey Lake w/themed rooms near disney
Have fun with the whole family at this stylish place: themed bedrooms and a peaceful feeling. With Disney just 5 miles away and Universal Studios 15-20 minutes away, the resort offers endless fun. Storey Lake Resort also has many nearby shopping malls and dining options. From its resort-style pool, splash pad, and watersides to its clubhouse, poolside bars, fitness center, and lake-based activities, Storey Lake is the happy ending to your vacation rental search.

3bd/2.5b Close to Disney °Luxury Paradise Living
Welcome To our beautiful, peaceful piece of paradise. A family friendly home! Enjoy the beautiful views, luxury decor, fine foods near you, and all this home has to offer! This home is all about creating loving memories. This beautiful home is newly built has 3 bedrooms 2.5 bathrooms, over 2,000 sqft, all new furniture, and super fast internet speed. The resort has a large beach-entry pool, kids water park, beach volleyball, mini-golf, arcade, and gym.

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.

Cozy House with Private Pool. Kissimmee/Orlando
Travelers will love staying at this home for its perfect mix of comfort and fun. Enjoy a private pool to relax after a long day, plus a gas BBQ included for easy outdoor meals with family or friends. The spacious and cozy layout is ideal for unwinding, while the peaceful setting makes it feel like a true getaway. Whether you’re here to relax or explore, this home offers everything you need for an unforgettable stay.

Disney area 4-bedrooms spacious villa for rent
Our villa offers a pleasant and relaxing place for families at an affordable price. Rent a private villa with a gorgeous swimming pool in a family-oriented residential neighbourhood. It has an excellent conservation view and outdoor space with a small pond. This home is in Eagle Point, Poinciana Blvd. in Kissimmee, near the Walt Disney World Resort.

Storey Lake 5BR Townhome | Private Pool | Disney
Dream Getaway in Kissimmee! This spectacular townhouse with a pool, 5 bedrooms, and 4 bathrooms offers the perfect base to explore the theme parks and everything the Orlando area has to offer. With modern and stylish decor, this property is ideal for families or groups of up to 13 guests.

2026 Themed NEW 08 Bedrooms At Solara Resort
Our vacation homes will bring you to experience beyond a simple stay. You will be near the most famous themed parks in the world while feeling the comfort of your home, plus having the highest standard of luxury and modernity, with everything a vacation home in Orlando can offer you.
Popular amenities for Kissimmee rentals with a pool
House rentals with a pool

Themed 10-Bedroom | Sleeps 26 w/ Pool & Game Room!

Pet-Friendly Pool Home Near Orlando

New and Unique Disney Airbnb!

Stylish Home & Free Resort Access 2420

Private Pool Home Near Disney | 4BR Sleeps 10

Luxury Home w/ Pool & 6 Beds near Disney

Amazing 6BR Disney - Universal - Encore Resort 460

6BR Oasis w/ Private Pool, Game Room & Lanai
Apartment rentals with a pool

Ideal for Two Families • Sleeps 8 • Top Location

NEW APARTMENT WITH WATER PARK AND NEAR DISNEY

Stylish Condo 20 mins to Disney/King Bed

A luxurious living just 15 min/Disney

303_To Infinity & the Ocean Breeze Apartment

Chic Disney Resort Condo • Pool Access Near Parks

A 3BR Resort Style Divine Getaway Near Theme Parks

Disney Dream Condo · Resort Pool · 20 Min to Parks
Other holiday rentals with a pool

Paradise Lake Lodge

Aurora Lux| Heated Pool| Games Room| Mini Golf|BBQ

Bright & Modern Stay Closest to Disney

3 Bed Pool/Spa w/ Sunset Water in Margaritaville

Exquisite Luxury Home Minutes from All Theme Parks

COZY Villa w/ Private Pool & Game Room | Kissimmee

Movie Theater|Game Room|Pool Movies & Free Pool He

Magical Stays Near Disney
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $199 SGD | $208 SGD | $222 SGD | $198 SGD | $173 SGD | $185 SGD | $194 SGD | $171 SGD | $158 SGD | $167 SGD | $187 SGD | $221 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 $26 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
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- Rentals with pools United States
- Walt Disney World Resort
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Disney Springs
- SeaWorld Orlando
- Orlando / Kissimmee KOA
- Camping World Stadium
- Magic Kingdom Park
- Epcot
- Universal's Volcano Bay
- Kia Center
- Disney's Animal Kingdom Theme Park
- Reunion Resort Golf Courses - Palmer & Watson
- Discovery Cove
- University of Central Florida
- Old Town
- ESPN Wide World of Sports
- LEGOLAND Florida Resort
- Disney's Hollywood Studios
- ICON Park
- Aquatica
- ChampionsGate Golf Club
- Tinker Field







