Holiday rentals with a pool in Kissimmee

Pool Spa + Outdoor Entertainment | Golf Retreat

Escape to a one-of-a-kind golf retreat in Davenport, where resort-style outdoor living meets family-friendly entertainment. Spend your days relaxing by the private pool & spa, enjoying movies on the outdoor TV, and challenging the family in the Super Mario game room, all just minutes from Disney Whether you're planning a family vacation, golf getaway, or long weekend with friends, this beautifully renovated 4-bedroom home was designed for connection, comfort, and unforgettable Florida memories.

10 Min to Disney | Heated Pool, Games, King Bed

🏡 Tucked inside a gated community near Kissimmee’s top attractions, this bright, themed home is made for memorable family getaways. Enjoy friendly competition in the game room, unwind in the heated private pool (available upon request), or relax on the covered patio beneath the Florida sun. Just 11 minutes to Fun Spot America, 11 minutes to Old Town, and 12 minutes to Disney World, it’s the perfect home base for your Florida adventure. Book now and start creating unforgettable memories!

Luxury Villa! /Game Room/ Pool Heater

Luxury Villa on a gated community in Kissimmee (Four Corners). Modern. Situated 10 min. from Disney theme parks. Well decorated and presented. Game Room, Mini Gym, Beautiful, large pool deck which is totally enclosed and secluded. There is a private Pool and overflow Spa. Three Bedrooms and Bedroom one is separate from the main house but still enclosed in the building. This would be ideal for a young couple within the group as it has its own bathroom, small kitchen and also total privacy.

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.

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!

3 Bed Pool/Spa w/ Sunset Water in Margaritaville

Welcome to Sol Oasis Cove! This amazing pool / spa cottage has one bedroom on the first floor and 2 bedrooms upstairs with a balcony positioned perfect for the sunset over the lake! This property comes with all the comforts from home but worlds away. Conveniently located minutes from the Disney parks, a state-of-the art water park and newly opened 196,000 square foot shopping and dining district with multiple dining food and beverage options & brand-new movie theater.

4BR Disney & Universal Themed Villa Reunion Resort

Welcome to our newly remodeled 4BR/4BA luxury villa in Reunion, designed for families and groups seeking comfort, style, and a magical Orlando escape. Enjoy brand-new furnishings, modern finishes, Toy Story and Mickey themed bedrooms, a spacious open living area with massage chair, and a fully equipped game room featuring air hockey, arcade basketball, and PlayStation. Relax in your private screened pool with optional heating after unforgettable park days.

Orlando Dream Escape | Private Pool | Disney

Enjoy this beautiful renovated house with a private pool in Kissimmee. Ideal for families and groups of up to 8 guests. It has 3 bedrooms, 2 bathrooms, a sofa bed, a fully equipped kitchen, Wi-Fi, a washing machine, a dryer and free parking. Located near Disney, Universal, SeaWorld, restaurants and shops. Relax, enjoy the sun, and create unforgettable memories with family and friends. Just minutes from Orlando's main attractions ✅ Private pool

Montego Bay Retreat | 15 Min to Disney

Enjoy a stylish stay in this newly renovated 3-bedroom, 2-bath home, perfect for families and groups of up to 9 guests. Located only 15 minutes (8 miles) from Disney and close to Orlando’s top attractions, restaurants, and shopping. Relax in modern, comfortable spaces after a fun day at the parks. Outdoor grill available for $30/day (gas included). The perfect mix of location, comfort, and convenience for your Florida vacation! ✨

New Modern Home near Disney in Orlando

Located only a few minutes from Disney World Orlando, Theme Parks, Disney Springs and unique dining experience, your stay will be one to remember. You will be entertained for days with Orlando’s attractions, parks, golf courses, lakes, trails, malls, restaurants, and nearby cities and beaches With 6 beds and a sofa bed, there's more than enough room for the whole group to get a comfortable night's rest from the day's adventures

Paradise Lake Lodge

A beautiful chalet-style home. If you're looking for a romantic or peaceful getaway, this house promises to provide an unforgettable experience, ideal for relaxing, vacationing, or living surrounded by nature. Unique sunsets overlooking the lake, a true oasis where comfort meets natural beauty. This home is located just 25 minutes from Orlando International Airport and 30 minutes from Disney and Universal Studios Florida.

Luxe Family Retreat | Pool Villa Near Disney & MCO

Escape to this beautifully designed family retreat featuring a private screened pool, BBQ gazebo, foosball table, spacious open-concept living areas, and a fully equipped kitchen. Ideally located near Disney, MCO Airport, outlets, shopping, restaurants, and Orlando’s top attractions. Perfect for family vacations, group trips, or a relaxing getaway with all the comforts of home.