Holiday rentals with a pool in Osceola County

The Sun-Kissed Retreat / near Disney

Welcome to your Orlando retreat! This spacious 5-bedroom, 4.5-bathroom townhome at the exclusive Azur Resort offers everything you need for an unforgettable vacation. Designed with comfort and style in mind, this home is ideal for families, groups, and anyone looking to explore the magic of Orlando. Located just mins from Orlando's top attractions- Disney World, Universal, and world-class shopping and dining. You’re at the center of it all! Book now and start making memories at the Azur Resort!

*Private Golf-Front Oasis with Pool, Spa & Cinema

Escape to one of Reunion Resort's most unforgettable homes, where luxury meets nonstop fun just minutes from Disney. Enjoy your private pool & spillover spa on the sprawling 2,000 sq ft pool deck, then take in golf course views from the separate fire pit terrace & balcony. Inside, discover a Star Wars theater/game room with digital pinball, arcade games & karaoke, a Marvel kids' suite with tube slide, Xbox Series S, and a hidden Harry Potter cupboard. Perfect for unforgettable family vacations.

Rustic Barn Retreat

Experience the rustic elegance of this beautifully remodeled 1,800 sq. ft. barn nestled on a serene 17-acre property. Unwind in the private heated hot tub and soak up the peaceful surroundings. The prime location offers convenient access to major attractions—just a 35-45 min drive west will take you to Disney, Universal, SeaWorld, and gator parks, while a 45-60 min drive east leads you to the breathtaking Atlantic beaches and the Space Coast. Plus, the property is only 40 min from the airport

Bamboo Bus -Sauna/Pool/Fire pit/Grill

Bamboo Bus is a unique, romantic and tranquil spa like getaway, perfect for relaxing with your significant other, family or friends. Enjoy the pool, unwind in the barrel sauna, grill your favorite meals and gather around the fire pit for s’mores under the stars. Located less than a mile from Lake Pierce, bring your kayaks and explore nearby lakes and state parks. Just 20 mins to LEGOLAND and 50 mins to Disney, it’s the perfect peaceful escape with easy access to Central Florida attractions.

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.

Orlando Dream Escape | Private Pool | Disney

Disfruta de esta hermosa casa renovada con piscina privada en Kissimmee. Ideal para familias y grupos de hasta 8 huéspedes. Cuenta con 3 habitaciones, 2 baños, sofá cama, cocina totalmente equipada, Wi-Fi, lavadora, secadora y estacionamiento gratuito. Ubicada cerca de Disney, Universal, SeaWorld, restaurantes y tiendas. Relájate, disfruta del sol y crea recuerdos inolvidables con familia y amigos. ¡A solo minutos de las principales atracciones de Orlando ✅ Piscina privada

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!

Stunning 6BR Lakeview at Storey Lake Disney - 2929

Modern luxury home with lake view, recently built, best location in town, at world-known Storey Lake Resort. Almost 4,000sf of a/c area, featuring 6 bedrooms, 6 full baths, game room, private pool, and spa. 3 Minutes away from Super Target, Publix Supermarket and Walmart 15 Minutes away from Disney Parks 15 Minutes away from Premium Outlets 20 Minutes away from Universal Studios 20 Minutes away from International Dr attractions *PLEASE MAKE SURE TO READ THE HOUSE RULES*

10 Min to Disney | Kings | Heated Pool | Games

✨ Perfect family getaway just minutes from Disney magic! ✨ This spacious 4-bedroom home sleeps 9 and features 2 king beds, 4 full beds, and 1 twin, plus fun Mickey Mouse & Minion themed rooms kids love. Unwind in your private screened pool, enjoy the game room with arcade games, ping pong, foosball & pool table, or relax with cozy board-game nights. 🏰 Animal Kingdom 10 mins Epcot & Hollywood Studios 15 mins Book now and start making unforgettable family memories!

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.

Royal Retreat Disney Themed Pool Home, Arcade, Theater

Welcome to The Royal Retreat. Located just 10 miles away from the entrance of WDW, our rental is the perfect place to stay for your Disney vacation. Our 5 star home features 8 themed bedrooms and 5 bathrooms, a fully-equipped kitchen, private heated pool, private arcade, home theater & BBQ! Free Pool heat & the 1st tank of propane for the BBQ are included. Booking with us includes full access to the Champions Gate Clubhouse, Oasis Resort and Retreat Club!

7851 Luxury 5BR Home w/ Private Pool Near Disney

Create unforgettable memories in this modern 5-bedroom, 5-bathroom home in Reunion Village, near Disney. Enjoy a private screened-in pool, game room, second-floor loft, open-concept living and dining area, modern kitchen, multiple king-sized bedrooms, themed bedrooms, high-speed Wi-Fi, TVs, washer/dryer, free parking, self check-in, and access to eligible Encore Club amenities. Ideal for families and groups.