
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.

Lakeside Paradise, 15 min Disney + Saltwater Pool
Welcome to Lakeside Paradise – Discover the perfect blend of tranquility and excitement at Lakeside Paradise. Enjoy the serenity of our lakeside retreat, just moments from Central Florida’s top attractions: Disney Parks – 8 miles (15 mins) Universal Studios – 16 miles (25 mins) SeaWorld – 13 miles (20 mins) ESPN Sports Complex – 6 miles (10 mins) Margaritaville/Island H2O – 3 miles (10 mins) Walmart/Target – 6 miles (10 mins) Optional heated pool and spa available for an added fee of $40/day

Waterfront next to Resort by Disney Game &Theater
Lakefront Luxury Everything is Completely remodeled 5 bdrms\5 bthrms luxury villa – Located in the gated Paradise Palms Resort,which is just around the corner from Disney. Only a few steps away from the Clubhouse amenities & nature path,this home offers privacy & lake\nature views from the sun soaked south facing color changing pool\spa.Enjoy , New home theater, two 1st floor master bdrms & 2 bthrms + another master & immersive themed rooms on 2nd floor. AC Arcade TV gameroom & billiards Loft

8BR Lakefront themed Villa•Pool•GameRoom•GolfCart
Stay minutes from Disney in a spacious 8BR, 4.5BA villa designed for families & groups! Kids will love the Mario Kart, Frozen, Toy Story, Small World & Royal themed rooms, plus a Harry Potter game room with pool table & arcades. Adults will enjoy the private pool, lanai patio, gourmet kitchen, Beauty & the Beast dining room, and the convenience of a golf cart included with your stay. Perfect for: • Multi-family Disney trips • Large groups (sleeps 16+) • Guests wanting both space & magic

Luxurious 5BR w/ Pool, Spa, Game Room & BBQ Grill
Step into your dream getaway at Windsor Island Resort, a stunning vacation retreat in Kissimmee with a private pool, relaxing spa, and full resort-style amenities. Just 10 miles from Disney and close to Orlando’s top attractions, this spacious home is perfect for families and friends. Whether you’re floating down the lazy river, enjoying a game of basketball, or simply unwinding in your own private oasis, this villa combines comfort, fun, and convenience for an unforgettable vacation.

Gorgeous 5BR @ Encore Next to Disney - 305
Modern 3,000sf luxury home, with 5 bedrooms, at world's renowned Encore Resort at Reunion. Featuring 5 bedrooms, 5 1/2 bathrooms, a game room, a beautiful backyard, a private pool and spa. 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 HOUSE RULES*

Luxury Townhouse Near Disney | 3BR
Enjoy a brand new, beautifully designed townhouse located in the exclusive Magic Village community, just minutes away from Disney Parks. What you’ll love: • Private patio with outdoor furniture • Free Wi-Fi • Fresh towels & linens • Fully equipped kitchen • BBQ grill (no additional fee) • Free parking (no extra cost) The pool, tennis court and fitness center should pay $100 extra fee per group per day. ✨ Book now and enjoy a memorable stay near the magic!

Upstay-Luxury 3BR Home w Private Pool & Games Room
Escape to your own resort retreat—just 17 miles from Disney! Splash in the private screened-in pool, unwind in the chic living area, or challenge the crew to games upstairs. This vibrant 3-bedroom home features a King and Queen bedroom and a fun Minions-themed bunk room, full kitchen, Smart TVs, and in-home laundry. With BBQ, resort-style clubhouse access, and family-friendly vibes, it's the ultimate Florida getaway! Your dream adventure starts right here.

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

Heated pool~Lazy River~Mini Golf~Near DisneyResort
Welcome to Lazy Lagoon, your ultimate vacation retreat in the heart of Kissimmee, FL! Our inviting 4-bedroom, 3-bathroom home offers the perfect blend of comfort and adventure, making it ideal for families, friends, or any group getaway. With space to accommodate up to 10 guests, you'll find everything you need for an unforgettable stay just minutes from Orlando's top attractions.

4Bd/ 4.5 Ba Sleeps 12! Solara Resort (2378ZP)
• Community: Solara Resort • 4 Bedrooms/ 4.5 Bathrooms/ Sleeps 12 • Clubhouse (0.9 miles) Walmart (4.1 miles) Publix (4.1 miles) • Disney World® (7.3 miles) SeaWorld (16.4 miles) • Convention Center (17.5 miles) ICON Park (19.5 miles) • Universal Studios (20.2 miles) Epic Universe (19.2 miles)i) • Location: Zaballina Place, Kissimmee FL 34747

Cozy Modern 1 Bedroom Apartment
Warm welcome to our modern one bedroom apartment. We are happy to be your host for your stay. Located minutes away from attractions such as Walt Disney World and Universal Studios. During your stay you will find comfort with a brew of a delicious cup of coffee as the sun rises. Book your next stay with us. We would love to be your host!

Boutique Luxury Home, Private Pool Close to Disney
Spend a unique boutique experience, just minutes from Walt Disney World theme parks, in this stylish 6-bedroom, 6-bathroom home that can comfortably accommodate 12 people. The house features a private pool, an Al fresco dining area with a BBQ and a lovely view to the golf court at Reunion Resort.
Popular amenities for Kissimmee rentals with a pool
House rentals with a pool

3BR Family Home near Orlando!

4 Miles to Disney! Private pool -5 Bedroom Home

(Discounted Rates) Vacation Home (4 Miles Disney)

5BD Formosa Gardens Near Disney (FG 7939)

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

Disney-themed, Private Pool with heat, King Bed!

Disney Villa - Waterpark, Walkable to Oasis

Home, Private Pool, 10 min to Disney, 3 BR/2 Baths
Apartment rentals with a pool

Magical Stay Near Disney & ESPN

8-108 Legacy Dunes, Lake View, Close to Disney

Storey Lake Themed 3BR w/ Resort Pool- near Parks!

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

3171-107 Resort Lake View Disney Universal Orlando

Westgate Vacation Villas - 1 Bedroom

*Sunset Perch: Views, Reunion Resort, XBox, 2Pools

Fully Renovated 3/2 Villa close to Disney parks
Other holiday rentals with a pool

The Disney House • Immersive Rooms • Gaming Lounge

Casita Disney! Cozy and Boho Townhouse near Disney

2BR condo in Bahama Bay ground floor big patio

Magical 3bd Townhome near Disney

5BR Home w/Pool near Disney Animal Kingdom

Spacious 3BR/2BA Retreat • Near Disney

The Villa Retreat / near Disney

SuperHost - 15 Mins to Magic Kingdom!
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $187 SGD | $190 SGD | $199 SGD | $195 SGD | $171 SGD | $182 SGD | $191 SGD | $168 SGD | $155 SGD | $164 SGD | $185 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 6,620 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 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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- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort
- Walt Disney World Resort Golf
- Disney Springs
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- ESPN Wide World of Sports
- Give Kids the World Village
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Aquatica
- Camping World Stadium
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
- Reunion Resort Golf Courses - Palmer & Watson






