
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.

Mickey's Lakefront Villa at Sunset Lakes
Updated Pics Dec 2024. We have no gas burning appliances. We abide by the AirBnB enhanced cleaning protocol. We want our guests to be happy, healthy and safe in their home away from home. Please see house rules. Located in beautiful Sunset Lakes – it's hard to find a vacation home closer to Walt Disney World with all that's offered at Mickey’s Lakefront Villa. Be amazed at how quiet and secluded you will feel yet just minutes away from all of the entertainment that you came here to enjoy.

Last minute deal - special prices
Beautiful modern home with 3 full suites and 3 bathrooms — a rare find in the area! Located in the gated community THE HUB, featuring new construction, an American-style kitchen integrated with the TV room, and pet-friendly accommodations (rules apply). The community also offers a swimming pool and a small gym for guests. Guests enjoy: 🕒 24h self check-in 🔐 Unique access code valid only during the stay 🛏️ Linens and towels provided 🐾 Pet-friendly (check rules) 🏊 Community pool & small gym

Destination Sunsation!1 Bedroom Villa 1st Floor!
Runaway Beach Club Resort located 2.5 miles from Disney World. You can choose to be part of the Orlando landscape or unwind and relax on the grounds and enjoy a lazy day at the pool. More amenities have been added as you now have access to Calypso Cay, including Mini Golf, additional pools, basketball & volleyball courts & children's playground and splash pad! We are a gated family friendly community. Less than a mile away there is a super walmart for any last minute needs!

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!

Modern King Apt w Water view, Pool Gym Near Parks
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

3-103 Legacy Dunes, Heated Pool, Free Wifi/Parking
Two Bedrooms 1 Queen Sized Bed 2 Twin Sized Beds 1 Queen Sized Sofa Sleeper bed Sleeps up to 6 Guests Two Full Bathrooms Ground Floor, No Stairs to Climb Fully Equipped Kitchen Close to Shopping and Restaurants Screened Patio with Seating Washer and Dryer Heated Outdoor Swimming Pool Close to Disney Free Wi-Fi and Free Parking Game Room Playground Tennis, Pickleball, Basketball, Volleyball Gated Community

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.

Luxury 3BR Pool Home at Paradise Palms
Enjoy a relaxing and unforgettable stay at this elegant 3bedroom, 3bathroom home located in the gated Paradise Palms Resort, just 15 minutes from Walt Disney World. Designed for families seeking comfort, fun, and convenience, this home features a private heated pool, open living spaces, and full access to exceptional resort amenities — all within walking distance.

Perfect Disney Relaxation! Water Park, Lazy River!
Welcome to Perfect Disney Relaxation at the highly-rated Solterra Resort, with one of the best water parks in the area featuring a Water Slide, a Lazy River, Zero entry pools, and spas. This fully equipped and upgraded private pool home offers everything for a perfect vacation, including poolside dining.

5 BD/3BA Single Level Home! Veranda Palms (4458NP)
• Community: Veranda Palms • 5 Bedrooms/ 3 Bathrooms/ Sleeps 14 • Disney World® (5.8 miles) SeaWorld (9.0 miles) • Convention Center (10.1 miles) Legoland (32.2 miles) • Universal Studios (12.8 miles) Epic Universe (11.8 miles) • Location: Nirvana Parkway, Kissimmee FL 34746

6 Bd/5 Ba Sleeps 13! Storey Lake (2664 sq ft)
• Community: Storey Lake • 6 Bedrooms/5 Bathrooms/ Sleeps 13 • Disney (7.0 mi) SeaWorld (9.7 mi) Legoland (37.4 mi) • Convention Center (10.8 mi) Universal Studios (14.0 mi) • Location: Scrapbook Street, Kissimmee FL 34746

Luxurious Dream 4/3 Bedroom Home w/private Pool
Located a short 15 minute drive to Disney, this luxury design inspired 4 bedroom, 3.5 bath is perfect for a family, multi family or romantic weekend away with your favourite person.
Popular amenities for Kissimmee rentals with a pool
House rentals with a pool

Disney Retreat | Huge Pool with Spa | 2 King beds

NEW 07 Bedroom Themed Luxury in Solara Resort

Fantabulous Disney Vacation House / 10 min Disney

Disney Themes Villa | Pool+Gameroom | Near Parks

Lakeside Paradise, 15 min Disney + Saltwater Pool

Resort TH 2b/2.5b With Private Hot Tub near Disney

Disney Villa - Waterpark, Walkable to Oasis

Reunion Village Hideaway
Apartment rentals with a pool

Coastal Retreat | 15 min to Disney

Perfect for Two Families • Sleeps 8 • Top Location

Stylish Condo 20 mins to Disney/King Bed

Resort Style Sunshine Oasis near Theme Parks

Golf Front Luxury Penthouse: Views, Marvel, 2Pools

Resort condo minutes from Disney!!!

Luxurious Spot 10 Mins Away to Most Attractions!!!

*NEW* Adventureland Stay / Sleeps 6 / Near Disney
Other holiday rentals with a pool

The Disney House • Immersive Rooms • Gaming Lounge

Best Value BnB Disney Villa W/ Private Pool & SPA

WorldQuest 3B2B Condo 15 min to Disney – Sleeps 8

Bright & Modern Stay Closest to Disney

Fairy Tale House at Solara Resort

“Casa Del Sol”

Modern Luxury Themed 7 Bed Pool Villa near Disney

Relaxing Home near Disney with a Pool & Spa
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $188 SGD | $190 SGD | $199 SGD | $195 SGD | $171 SGD | $183 SGD | $191 SGD | $168 SGD | $156 SGD | $165 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 $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






