
Vacation 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.

PentHouse Suite with 2X View
Located at the gates of Walt Disney World, this Awesome PentHouse Suite offers easy access to area theme parks, and entertainment venues in the surrounding area, including Walt Disney World, Universal Studios, Sea-world, Legoland + Amazing Restaurants, Shopping and many more. Best of all wonderful views with 2 Large Balcony's, 1 for Sunrise @ East Side and 1 for Sunset @ West side overlooking Disney World with amazing fireworks every night, Enjoy! **Security camera for safety @ Entry door only!

3161-305 Resort Lake View Disney Universal Orlando
Minutes from Disney World Orlando Florida, Modern & Stylish 2bed/2bath fully equipped apartment for up to 7 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!

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.

207_ Sparkle Apartment Close to Disney Free Waterp
Newly Remodeled Mickey-Themed Apartment – Perfect for Your Getaway! Experience the magic in our beautifully remodeled apartment, designed to make you feel right at home! Whether you're visiting the parks or exploring Orlando, our space offers everything you need for a comfortable and unforgettable stay. Plus, enjoy free access to an exciting waterpark—the perfect way to relax and cool off after a day of adventure. And don’t miss the breathtaking fireworks featuring Mickey's Bedroom (LED Lights)!

Fireworks Penthouse: Top Floor, Star Wars, 2 Pools
This modern 3-bedroom TOP FLOOR (with an ELEVATOR right to the door) luxury condo has one of the most PICTURESQUE VIEWS in the Reunion Resort of the Arnold Palmer PGA golf course. Combining STYLISH DESIGN and LUXURIOUS COMFORT, there are 2 KING bedrooms and a playful STAR WARS themed bedroom with a classic Arcade machine & Xbox. 4 TVs with DirecTV, free high-speed wifi, your own washer & dryer, access to 6 resort pools, 2 of which are only a 3 minute walk away, and only a short drive to Disney.

Cozy Disney Oasis Pool Home 10 Mins from Parks!
Our charming, pet-friendly home is located in the prime area of Kissimmee, Florida. Your family will be close to Disney parks, restaurants, Old Town, and Downtown Disney. Just bring your bag—we have everything you need! Settle into our fully equipped home, thoughtfully designed to create lasting memories with family and friends. Enjoy the Florida weather by cooling off in our open-air pool or grilling by the poolside lounges. Relax in our airy bedrooms, including Mickey and Minnie themed rooms!

Dreamy Waterside Villa | Heated Pool & Near Disney
Experience a quiet waterfront villa, this stunning property offers breathtaking views, luxurious amenities, and prime location for your getaway. Relax by the pool enjoying the unwind lake view, With spacious interiors, modern furnishings, and impeccable attention to detail. Whether you're seeking relaxation or adventure, is your perfect vacation home. Book your stay at our stunning home and create unforgettable memories with your loved ones. NO PARTIES/NO SMOKE $50 pet fee $35 pool heater fee

Modern House with Private Pool Getaway Kissimmee
This property is accommodated for families looking to vacation with peace of mind, the facilities are perfectly arranged so that you and your family feel at home. It has 3 rooms equipped for adults and children, the patio area is the perfect place to spend time with your family either in the pool or enjoying a barbecue on the grill.( POOL IS NOT HEATED) -No parties allowed in the house. No smoke. Do not park blocking the sidewalk, no park on the grass, nor in front of the neighbors' house.

Epcot Themed Home: Private Sunset Near Disney
LOCATION! LOCATION! LOCATION! Hello all my globetrotters! Our fun home features a diverse international culture in each room. Experience Italy in the kitchen, America in the living room, Japan in the game room, and sleep in Paris, China or Morocco bedrooms. In the backyard, Mexico awaits with amazing private pool and a glow party at sunset each night. Depend on traffic, between 10-20 min to Disney, fast WiFi, ample natural light, tons of nearby grocery stores, restaurants, and shopping

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)

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.
Popular amenities for Kissimmee rentals with a pool
House rentals with a pool

"Sunny Oasis" Huge Pool Deck/Movie Theatre/Arcade

Minutes to Disney! Pvt Heated Pool. Sleeps 10

Kissimmee, Heated pool, Luxury

Brand New - 12br - Sleeps 30 - Theatre/Arcade/Pool

The Eights House by Disney. Themed Island Dream

Magical Family Fun House Near Disney Luxury Villa

Large Private Home on Golf course by Disney

No Airbnb Fee | Luxury 7BR w/ Cinema & EV Charger!
Condo rentals with a pool

Beautiful Beach Style Condo minutes from Disney

Chic Disney Condo w/ Resort, Pool & Near Parks

Modern Lake view Condo 1 mile from Disney

Luxurious Spot 10 Mins Away to Most Attractions!!!

BRAND NEW CONDO- 2 BR 2 Bath-Great location!

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

SL106 - Modern Condo - Resort Access included

Lakefront Resort Condo near Disney & Universal
Home rentals with a private pool

Wr001or (1stfororlando)

Disney's Championsgate: Private Pool & Arcade Fun!

1116chd-The Retreat at Championsgate

Airy, Stylish Home with Pool Heat Included in Davenport

Visit Disney World from a Sunny Home with a Pool

5268oba-Solterra Resort

The Manors at Westridge Home W/ Private Pool

4323sl-Storey Lake Resort
Quick stats about vacation rentals with a pool in Kissimmee
Total rentals
6.6K properties
Total number of reviews
235K reviews
Family-friendly rentals
5.8K properties are a good fit for families
Pet-friendly rentals
1K properties allow pets
Rentals with dedicated workspaces
3.6K properties have a dedicated workspace
Wifi availability
6.4K properties include access to wifi
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- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Universal's Volcano Bay
- SeaWorld Orlando
- Disney Springs
- Discovery Cove
- Old Town Kissimmee
- Disney's Animal Kingdom Theme Park
- Magic Kingdom Park
- Epcot
- ESPN Wide World of Sports
- Amway Center
- Reunion Resort Golf Courses - Palmer & Watson
- Walt Disney World Resort Golf
- Aquatica
- Island H2O Water Park
- Disney's Hollywood Studios
- ICON Park
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
- Kissimmee Lakefront Park
- Universal's Islands of Adventure
- Ventura Country Club