
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.

3150-303 Resort Pool View Disney Universal Orlando
Minutes from Disney World Orlando Florida, Modern & Stylish 2bed/2bath fully equipped apartment for up to 6 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!

Near Disney/Kid-Friendly/Disney-Themed/Water Park
Your magical vacation starts here! Just 15 minutes from Disney World, this beautiful, family-friendly home offers luxury, themed rooms, and fun, perfect for creating unforgettable memories. The home is located in the ChampionsGate area. It has 3 bedrooms, 2.5 bathrooms, modern furniture, and super fast internet. You will have free access to the Enclaves at Festival amenities center which features a large beach-entry pool, kids water park, beach volleyball, mini-golf, restaurant, and gym.

Disney & Universal Retreat| Heated Pool | Fire Pit
Sit back and relax in this stylish home with all the amenities you need for a fun family getaway. This home has a spacious layout with 3 bedrooms and 2 baths. We have thought of everything so you don't have to-toiletries,washer/dryer, and wifi. Enjoy your morning coffee in the screened in pool area with a beautiful sunrise and lake view or sip a glass of wine while floating in the pool. Just minutes to Theme Parks and major highways, this is the dream home you have been waiting for!

Chic Vibes Comfy King Bed Next to Parks/Food/shops
Welcome to our stylish oasis in Kissimmee, which seamlessly blends sophistication with a laid-back vibe. Your stay begins in a professionally cleaned apartment for your full enjoyment. Discover resort-style amenities – a sparkling pool, a fitness center, and hammocks, offering the luxuries of a five-star retreat. Conveniently located with in walking distance of theme parks, restaurants, and shopping. Book now. We can't wait to host you in our little slice of paradise!

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 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. **

Heated Pool 15 Minutes to Disney PS5 l Switch
Spacious 4BR Home with a Private Heated Pool – 15 Minutes from Disney! Enjoy a large south-facing pool, Propane grill, Smart TVs with Disney+ in every room. Nintendo Switch in Living Room and an 85" screen with a PS5 in a temperature-controlled garage / game room. Fast WiFi, shuffleboard, pool table and plenty of board games. 🌴 Outdoor Fun Patio Seating for 14 + two lounge chairs. Propane Grill: $50 for length of stay Pool heat: $200 per stay (24-hour notice)

Great reviews! Tiny home in quiet & safe area
Cozy cottage located only 4 MILES TO DISNEY WORLD!!! The cottage is so close to everything yet surrounded by lush trees, established landscaping and an ever so peaceful setting. 10 minute walk to ALDI, Dunkin Donuts, Chilis, Longhorn, Krispy Kreme, Dollar Tree, Waffle House, IHOP, Cracker Barrel, CVS and much more! 2 miles to Wal-Mart. 7 miles to Sea World. 8 miles to Orange County Convention Center. 13 miles to Universal Studios. 14 miles to Premium Outlet.

♥︎ Disney-3 miles ♥︎ Private HotTub ♥︎Top Resort♥︎
Our gated-community townhouse offers a resort feeling with all the comforts of home, peaceful & quiet, yet central to Disney, Old Town, and all major attractions. After an exciting family day, relax in your private patio hot tub and enjoy the nature, or soak up some sun poolside at the resort. Fun for adults and kids of all ages! Also enjoy the resort tennis courts, pool table, gym, restaurant, and poolside snack bar! NO RESORT FEES! FREE PARKING!

Manor on Knottingham Near Disney
Welcome to "Manor on Knottingham," nestled in the heart of Four Corners. The rustic charm, adorned with vintage Disney-inspired decor, transports guests to a bygone era of beloved characters and timeless tales. Outside, enjoy the sparkling blue pool and warm summer weather. A great place for family and friends. "Manor on. Knottingham" promises an extraordinary stay, where the magic of Disney and the comfort of a home merge into an unforgettable experience.

Kid-Approved Stay – Pool, Parks & Themed Rooms!
Give your family a stay they’ll never forget! Kids can rule their own Frozen kingdom or battle in a galaxy far, far away, while adults unwind after action-packed park days. ✔ Themed kids’ rooms – Frozen castle & intergalactic escape ✔ Private splash pool for a refreshing break ✔ Spacious & modern layout for families & groups ✔ Prime location near Disney, dining & top attractions Don’t miss out—book Let It Go Galaxy before it’s gone!

Entire Modern Home near Disney • Pool & Game Room
Make memories at our beautifully renovated home in Kissimmee — close to Disney, Universal, and everything Orlando has to offer. Relax in your private pool, enjoy 3 comfortable bedrooms and 2 full baths, and check in easily with keyless entry. Nestled in the safe, gated community of Cumbrian Lakes, it’s the perfect spot for families and friends to unwind together.
Popular amenities for Kissimmee rentals with a pool
House rentals with a pool

5 Bedrooms/4 Bathrooms Storey Lake (2689 SS)

No Airbnb Fees! Home Pvt Pool/SPA in Resort 244381

Modern 4bd house/heated pool,Close to Disney

3 bedroom Villa in Kissimmee

Waterfront Wizarding Near Universal's Harry Potter

Awesome Vacation Home w/ Private Heated Pool/Spa

Game & Theater Room, Castle Bunks, Pool & Spa

"Sunny Oasis" Huge Pool Deck/Movie Theatre/Arcade
Condo rentals with a pool

P-Gated Resort-5 miles to Disney-2 FREE Water Park

Bright, Roomy Stay by Orlando’s Best Attractions

Beautiful Lake View Condo. Close to Disney.

Enchanting Newly Renovated 1.5miles to Disney (760

Waterfront Resort Condo near Disney and Universal

Renovated First Floor Disney Family Condo

Sol y Mar Resort Style Condo - NO RESORT FEES

Modern Apartment with lake view Close to Disney
Home rentals with a private pool

Wr001or (1stfororlando)

Disney's Championsgate: Private Pool & Arcade Fun!

Beautiful 9 Br Pool Home In the Solterra Resort!

Airy, Stylish Home with Pool Heat Included in Davenport

Visit Disney World from a Sunny Home with a Pool

The Manors at Westridge Home W/ Private Pool

4323sl-Storey Lake Resort

New! Brand New Encore Resort 5 Bed Resort Home
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $225 AUD | $228 AUD | $239 AUD | $234 AUD | $205 AUD | $219 AUD | $230 AUD | $202 AUD | $187 AUD | $199 AUD | $213 AUD | $251 AUD |
| 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 6,590 holiday rentals in Kissimmee

Verified guest reviews
Over 234,830 verified reviews to help you choose

Family-friendly holiday rentals
5,770 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 1,010 rentals that welcome pets

Rentals with dedicated workspaces
3,650 properties have a dedicated workspace

Wi-Fi availability
6,440 of Kissimmee holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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
- Universal's Volcano Bay
- Disney Springs
- SeaWorld Orlando
- Disney's Animal Kingdom Theme Park
- Magic Kingdom Park
- Old Town Kissimmee
- Walt Disney World Resort Golf
- Epcot
- ESPN Wide World of Sports
- Amway Center
- Reunion Resort Golf Courses - Palmer & Watson
- Discovery Cove
- Aquatica
- Island H2O Water Park
- Disney's Hollywood Studios
- ICON Park
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
- Universal's Islands of Adventure
- Ventura Country Club
- Kissimmee Lakefront Park






