
Vacation rentals with a pool in Osceola County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Osceola County
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.

Near Disney Gated LakeView Pvt Heated Pool
LIMITED PROMOTION! FREE CLEANING FOR BOOKING 2 WKS OR MORE! LOWEST CLEANING FEE! Military dscnts. New Pool Heatr, Dolby ATMOS, 65" LED TV w/ Airplay. Remote office setup. Sunset Lakes a secure gated comnty ~12 min from Disney & other parks. Villa offers Lake View pvt pool, gorgeous sunset, Playroom, Fishing dock. Fully furnished, sparkling clean w/ 5 bds - 1 King, 2 Qns, 2 Twin beds w/ 3 baths, kitchen & lndry. Come & enjoy your next trip to Disney & leave everything to a fantastic experience!

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!

Amazing Blue Private Pool • 4BR House Near Disney
🏡 Spacious 4BR Home w/ Private Pool – 🐶 Pet-Friendly (Upon Approval) & 15 Min to Disney! Enjoy your well-deserved vacation in this family-friendly 4BR home with a private pool just for you! After an exciting day at the parks, unwind in your own backyard oasis. 🚗 Prime Location: ⭐ 15 min – Disney Parks ⭐ 20 min – SeaWorld, Disney Springs, Margaritaville ⭐ 20-25 min – Universal / Epic Universe & SeaWorld ⭐ 30 min – Orlando Intl Airport (MCO) ✨ Book now for the perfect Orlando getaway! 🎢🏡

Tahiti Gil’s Mananui: Disney Poly & Tiki Inspired!
Aloha Adventurers! Welcome to Faré Mananui. Your passport to a far away tropical hideaway awaits, so get ready to grab your favorite Aloha shirt! Mananui was made for the Disney/Tiki ADULT in mind! Imagined by artist @TahitiGil & designed by @TyphoonTommy (Former Disney/Universal creative team & designer of the Suffering Bastard Tiki Bar in Sanford, Fl. Experience your next Adventureland/ Enchanted Tiki Room “story dwelling” adventure from the moment you step thru the door! - Kungaloosh!!

*Private Golf-Front Oasis with Pool, Spa & Cinema
The perfect balance of STYLISH DESIGN, LUXURIOUS COMFORT, & ENDLESS ENTERTAINMENT, beautifully situated with stunning views in the sprawling 3.5 square mile Reunion Resort. You will have your own private pool, spillover spa, STAR WARS cinema-game room with pinball, classic arcade games, and karaoke, MARVEL kids room with tube slide and double bunks, the latest Xbox Series S, a sprawling 2000 ft2 pool deck, fire pit, and even a HARRY POTTER cupboard hidden under the stairs, minutes to Disney.

Amazing New Villa! Well Maintained! Fun for all!
My name is Mike and I’m the proud owner of Castle Pines Cove. This 6 bedroom Villa was completed and furnished in the spring of 2022. I love this house. I spend a lot of time here with my family. I have a 5 and 8 year-old and this is their favorite place to visit. It’s extremely important to me to ensure not only the house is clean but also maintained to the highest standard. Just like with my family, I want everyone who stays here to feel the exact same love for the house that we do.

Villa Resort Club
VILLA LUJOSA - BARRIO SÚPER HERMOSO POOL HEATER HOUSE - Diviértete con toda la familia en este alojamiento con estilo moderno , te encantará el área de picnic frente de la casa , el área de juegos y piscina con calentador , un espacioso lugar de hierba artificial para jugar tus niños y en una zona muy trankila cerca de los parques de Disney y del aereopuerto MCO . TE ENCANTARÁ LA CASA Local utility or county personnel may access exterior areas for maintenance without prior notice.

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*

Peaceful Waterfront Retreat, Close to Everything!
Beautiful 4br peaceful lakefront home in safe, quiet community. Close to major shopping and restaurants! Just a short drive to the Turnpike and 417 highway, close to Disney, Seaworld, Medical City, Lake Nona and the VA Hospital. Comfortable space with smart TVs and central AC. Fully equipped kitchen. Split floor plan perfect for families and friends. The master bedroom faces the rear of the home, large windows allowing natural light to enter the home all while enjoying your waterview!

Large Private Home on Golf course by Disney
Bring the whole family to this great place with lots of room for fun. With fantastic views of the 4th hole on the Tom Watson golf course and your own private pool and hot tub everyone will enjoy this stylish and modern vacation home. Located in premier Reunion Resort and only 10 minutes to Disney you can have it all! This home boats over 4000sq feet, two very large masters suites, 2 additional bedrooms and plenty of space throughout the home. There are 6 tvs! Pets are welcome too!

Themed 6BR | Game Room | Private Pool & Spa w/View
Stay at Time-Out Corner, Too @ Windsor Hills for an incredible vacation filled! Enjoy a game room, themed bedrooms, a private pool and spa w/gorgeous sunset view, and more. Plus, free access to the resort’s clubhouse and water park. Just 5 mins from Disney! 🎮Toy Story Game Room. Play Air Hockey, Skee-Ball, Arcades, Xbox, PlayStation, and more. 🏊 Private West-Facing Heated Pool/Spa. 🛏️ 6 BR & 4 BA. 3 Themed Bedrooms (UP, Alice in Wonderland, and Orange Bird). Sleeps 14.
Popular amenities for Osceola County rentals with a pool
House rentals with a pool

Pool+Game Room 10 min to Disney sleeps 10

3 bedroom Villa in Kissimmee

Serene 4BR Pool Home Near Disney

Epic Home-FREE Water Park/Disney/South Facing Pool

S3910 | Near Disney Home w/ Pool & Games

8615 Vacation Oasis House Private Pool Grill

Luxury Lakeview 🏠 Game Room🕹Theater🍿Free Waterpark

The Eights House by Disney. Themed Island Dream
Condo rentals with a pool

Minutes to Disney best of Home, with a Resort feel

Stylish Condo 20 mins to Disney/King Bed

Pet friendly Orlando area near ESPN Center

Disney Dream Condo & Pool

1-104 Legacy Dunes, Pool View, Close to Disney

Modern Condo with Lake View Near Disney 3151

Like Home Family Getaway

Beautiful 2 BR/ 2 BA Condo in Windsor Palms Resort
Other vacation rentals with a pool

Luxury Serenity + Reunion Living Near Disney

Casita Disney! Cozy and Boho Townhouse near Disney

Orlando Oasis

Paradise Lake Lodge

The Sandy Gator

Mad Men Magic Kingdom House*FAB POOL*OutdoorMOVIE

Family Getaway Near Disney Magic - 20104

Palm Oasis near Disney
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- Rentals with pools United States
- Walt Disney World Resort
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Disney Springs
- SeaWorld Orlando
- Magic Kingdom Park
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Discovery Cove
- ESPN Wide World of Sports
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Camping World Stadium
- Aquatica
- Sebastian Inlet
- Playalinda Beach
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!




