Holiday rentals with a pool in Kissimmee

Sleeps 21|Free Pool Heat|15 min to Disney|Hot Tub

Make memories to last a lifetime in our luxurious seven-bedroom home (sleeps 21) at Orlando's premier vacation community. Enjoy your own Batman cave game room, private pool (heated at no extra charge*), and hot tub. Our 100% Five-Star rating from previous guests and our generous cancellation policy means you can book with confidence. Only 15 minutes to Disney and a short walk to a fabulous resort clubhouse with free access to a lavish pool, kids waterpark, restaurant, playground, gym, and more!

Affordable Disney Family Townhome Pool/BBQ/Gym

Welcome to your modern 3-bedroom, 2.5-bath townhouse in a resort community just minutes from Disney. Enjoy a spacious open-plan living area, fully equipped kitchen and private screened patio. Resort-style amenities include pools, clubhouse and fitness center. In a quiet, secure neighborhood, this home offers easy access to Orlando’s world-famous theme parks, shopping centers and restaurants. Perfect for families or groups looking to experience the magic of Florida with all the comforts of home.

8Bd 4K Movie Theater 155 Inch Screen Pool & Spa

A vacation home that takes your entertainment seriously! That’s our 8-bedroom villa in Emerald Island Resort at 3 miles from Disney… Ready to enjoy themed bedrooms, a premium private movie theater with a 155-inch screen, 4K projector, 5.1 surround sound, and a PS5 for gaming? Relive your favorite films in stunning quality, just like in the best movie theaters. Private Pool and Spa will make your vacation unforgettable! We’re ready for families and groups, to offer fun, comfort, and luxury.

Modern 3-BR Luxury Townhome – Perfect for Families

Welcome to your home away from home! This beautifully renovated, professionally decorated 3-bedroom, 2.5-bath townhome is designed for comfort and style, offering a spacious retreat for up to 6 guests (or 8 with the use of an air mattress). Featuring a modern open-concept kitchen, living, and dining area, high-speed internet, and thoughtful amenities, this professionally decorated space offers the perfect blend of comfort and convenience. Book your stay today and feel right at home!

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

Luxury Home w/ Pool & 6 Beds near Disney

Welcome to your modern escape in Kissimmee! Just 15 minutes from Orlando International Airport, this beautifully renovated 3-bedroom, 2-bath home offers the perfect blend of comfort and luxury. Every detail has been thoughtfully upgraded—from the brand-new kitchen and spa-like bathrooms to the pristine private pool area—ensuring a relaxing stay. With sleeping arrangements for up to 9 guests across six beds, there’s plenty of space to unwind.

Amazing 8Bdrms-5Bath/Game room/Pool

The Space * Accommodates: 22 * Bedrooms: 8 * Bathrooms: 5 * Property type: Luxury House * Location: Storey Lake * 12 miles from Magic Kingdom * 10 miles from Animal Kingdom * 16 miles from Universal Studios * 2.4 miles from Lake Buena Vista Factory Stores (Outlet) * 4 miles from The Loop (Outlet) * 22 miles from MCO * Located close to Highways 192 and 535, the property is located close to the main restaurants, pharmacies, markets.

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.

Private Pool Home Near Disney | 4BR Sleeps 10

Modern designer home with private pool, perfect for families and groups near Disney. Sleeps 10 in 4 stylish bedrooms and features a chef-style quartz kitchen, elegant dining for 8, spacious living area, and a fun kids’ room. Located in a quiet upscale community just 20–25 minutes from Disney, with easy access to Universal and Orlando’s top attractions.

Private Condo, Ideal for Groups. apt - 136

Experience an elevated stay in this 3 bedroom, 3 bathroom luxury condo accommodating up to 6 guests, located in the exclusive Spectrum Condos at Reunion Resort, just minutes from Orlando’s top attractions. Perfect for families and groups seeking privacy, comfort, and a refined resort setting.

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.

Amazing Themed 07 Bedrooms at Solara Resort

* Accommodates: * Bathrooms: 5 * Bedrooms: 07 * Property type: Luxury Villa * Location: Solara Resort