
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.

Your Happy Place at Tuscana Resort
Tuscana Resort 2 bedroom 2 bath condo - New Listing - Special Rates Accommodates the needs of all types of travelers that want a cozy place to relax after a long day out and about. Close to Theme Parks, Golfing and many of Orlandos attractions. Sleeps 6 guests in this spacious open concept condo. 65" Smart flat screen TV in the living room. Both bedrooms have TV's Fully equipped kitchen for dining at home. Located on the first floor for easy access and a minute walk to the community pool.

Waterfront Escape/Private Hot Tub/3 miles 2 Disney
Discover the ultimate vacation experience in this freshly updated waterfront townhome, where comfort meets breathtaking views from your private lanai, hot tub and dining area. Wake up to serene water vistas from the spacious primary suite, featuring a plush king bed and a private ensuite bath. The guest bedroom offers two inviting double beds and 3-piece ensuite. The open-concept kitchen is a chef's dream, outfitted with modern appliances and flowing seamlessly into the dining and living areas.

Luxury 5BR free heat private pool Disney Universal
Welcome to this gem near all major attractions: Disney (5 miles), SeaWorld (7 miles), Universal (12 miles), Convention Center (9 miles), and Airport (20 miles). Nearby are outlets, restaurants, and supermarkets. This luxurious home features 5 bedrooms, 4 bathrooms, a private heated pool/spa, fully equipped kitchen, laundry, and free stroller, playpen, and highchair. Resort amenities include a water complex, lazy river, bar, fitness center, mini golf, kayaking, and more! Pets friendly & welcome!

Disney World Area Executive Villa *Sleeps 10* Pool
Luxury Villa in the Disney Area of Orlando. 3 bedrooms and second floor living room with sofa bed, sleeping up to 10 guests Situated in the fabulous Highlands Reserve, Walt Disney World is only 25 minutes drive. The villa features a private screened pool with sundeck, perfect for outdoor dining Spacious accommodation and featuring a master suite with bathroom and walk in closet, children's rooms and games room Infant pushchair, highchair & cot/pac 'n' play Laundry & fully equipped kitchen

Luxury Themed 5BR-Pool-Game Room
This newly-built townhome in Solara Resort is boasting a perfect location near all of the famous amusement parks and attractions this area is known for, you will have no delay in spoiling the whole family with a day at Disney or Universal Studios. Take a relaxing dip in the private pool, grill up a few burgers on the grill, or simply reminisce with loved ones. Inside you will be spoiled by the modern touches throughout. The kiddos will absolutely love the Marvel and Disney-themed bedrooms.

VerandaPalms/HeatedPool/Carpet free/NearDisney
This beautiful 4 bedroom home is 10 minutes from the Disney parks !!! Walking distance from Shingle Creek Reg. Park, just in the corner of Veranda Palms main entrance. This home has 2 suites, a private heated pool and is located near Sams Club and restaurants. Complimentary XBOX and Nespresso Coffee machine. ROKU in all bedrooms. Non smoking policy. Clubhouse with large swimming pool and gym. Well-maintained home, with new appliances. Superhost awarded 34 times in a row !!!

"Paradise Found" Sensational 6 Bed Home W/Peloton
Discover 'Paradise Found' at Windsor at Westside, a 6-bed fantasy home near Disney. This 3,300 sq ft gem offers an open-plan living space, gourmet kitchen, and a private pool oasis with a BBQ, dining and lounge. Enjoy a king suite with pool access, a fun-filled garage gym/games area, and a vast upstairs lounge with Xbox. Dream in themed children's rooms or one of the three king bedrooms. Perfect for families seeking a magical retreat! Free resort access, pool heat and BBQ.

Contemporary Stay 10 min to Parks Pets Friendly
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

Premium 6BR | Theater, Games & Heated Pool
Welcome to your 3,400 sq ft luxury escape just minutes from Disney World! Perfect for families and friends, our villa sleeps 12 with ensuite bathrooms in every bedroom. Enjoy the home theater, game room, and a fully equipped kitchen—plenty of space to gather or relax. Close to shopping, dining, and all the Orlando magic. Book now for unforgettable memories in your private Disney-area villa.

2-104 Legacy Dunes, Lake View, Heated Pool, Gym
Two Bedrooms 1 King Sized Bed 1 Queen Sized Bed 1 Queen Sized Sleeper Sofa Bed Sleeps up to 6 Guests 2 Full Bathrooms Ground Floor, No Stairs to Climb Close to Walt Disney World Screened Patio with a Lake View Washer and Dryer Roku TV's Free Wi-Fi Free Parking Heated Outdoor Swimming pool Tennis Court, Basketball, Pickleball, Volleyball Game Room Playground Gym Gated Community

Haunted Mansion Retreat with pool 7 min to Disney
Our Haunted Mini Mansion is a delightful ghostly retreat where every room has wall-to-wall creeps! Enjoy this spooky 3 bedroom, 3 full bathroom private townhouse inspired by Disney’s Haunted Mansion. Hurry back to make your final arrangements!

4 Bd/3 Ba Sleeps 10! Lucaya Village (25-108)
• Community: Lucaya Village • 4 Bedrooms/3 Bathrooms/Sleeps 10 • Disney (5 miles) Sea World (7 miles) Universal (12 miles) • Convention Center (6 miles) Legoland (31 miles) • Location: Polynesian Isle Blvd, Kissimmee FL 34746
Popular amenities for Kissimmee rentals with a pool
House rentals with a pool

6BR 3.5BA Family Vacation Home

10 Min to Disney • Cozy Townhome + Jacuzzi + BBQ

Amazing 08Bdrms/Sleep 20/Pool/Close to Disney

4781 - 5BR w/ Pool | 10min Disney | 2 Water Parks

Gorgeous 5BR PetFriendly @Encore | Disney - 7693

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

Luxury 4 Bedroom Home - Resort Access! Disney!

2026 NEW Brand NEW 07 Bedrooms At Solara Resort
Apartment rentals with a pool

Stylish Condo 20 mins to Disney/King Bed

Disney Oasis by the lake

Luxurious Spot 10 Mins Away to Most Attractions!!!

Stunning Sunny Central Condo w/ Pool & Balcony

"Ocean's Gate" - 2BD/2BA condo near Disney

2-bedroom condo w/ stunning lake and Disney views

Poolside 3Br, Waterpark, Disney 2mi, Windsor Hills

Westgate Vacation Villas - 1 Bedroom
Other holiday rentals with a pool

Authentic Disney Fort Wilderness Cabin near WDW-1

Windsor Hills, Disney/Universal, Pool/SPA, 5BR5BA

Disney Escape/ 7 Resort Pools/New Built/Pond View

Magic Pond View TH 2b/2.5b Private Spa by Disney!

Executive Disney Home on Highlands Reserve

King Bed Apartment, Close to Disney

The Cozy Nook

4 bedroom home with pool & spa overlooking lake
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $189 SGD | $191 SGD | $200 SGD | $196 SGD | $172 SGD | $183 SGD | $192 SGD | $169 SGD | $156 SGD | $165 SGD | $186 SGD | $219 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 6,620 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 238,760 verified reviews to help you choose

Family-friendly holiday rentals
5,800 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 1,070 rentals that welcome pets

Rentals with dedicated workspaces
3,700 properties have a dedicated workspace

Wifi availability
6,590 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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- Walt Disney World Resort
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Disney Springs
- SeaWorld Orlando
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- ESPN Wide World of Sports
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Give Kids the World Village
- Camping World Stadium
- Aquatica
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- ChampionsGate Golf Club






