Vacation rentals with a pool in Kissimmee

4.82 out of 5 average rating, 249 reviews

Villa in Kissimmee

150 Inch 4K Movie Theater Pool & Spa sleeps 16

"Just 3 miles from Disney up to 16 guests! Unwind in the pool & jacuzzi. A private cutting-edge Movie Theater, featuring a 150-inch screen, 4K projector, and immersive surround sound. Relive your favorite movie moments like never before! Stream on Roku, game on PS5, and enjoy high-speed Wi-Fi for endless fun. The well-equipped kitchen is perfect for large families and with 6 bedrooms and 4 en-suite baths, privacy is guaranteed. A Star Wars and a Disney-themed rooms so the kids will feel at home.

5 out of 5 average rating, 8 reviews

Luxury Retreat at Reunion Resort

Luxury Retreat at Reunion Resort – 12 Miles from Disney! Welcome to 7471 Gathering Loop, a stunning vacation home nestled in the prestigious Reunion Resort! This elegant getaway offers the perfect blend of luxury, comfort, and convenience, making it an ideal retreat for families and groups. The home offers a beautiful back yard pool and spa area for you to enjoy, while playing music through the surround sound system in the house and in the back yard. With 6 Bedrooms You wont regret staying here.

5 out of 5 average rating, 40 reviews

Apartment in Kissimmee

Modern Luxury Kissimmee Retreat

Welcome to our stunning Kissimmee apartment, where modern luxury meets ultimate comfort! This renovated 2-bedroom, 2-bathroom retreat offers high-end finishes, a fully equipped kitchen, large screen TVs, PlayStation 5, and high-speed Wi-Fi. Enjoy blackout curtains and white noise machines for restful nights. Complex amenities include a pool, gym, sauna, and tennis court. Located near Walt Disney World, Universal Studios, and top shopping, our apartment is the perfect base for your adventures.

4.95 out of 5 average rating, 59 reviews

Villa in Orlando

The Lakeview Oasis - XL Pool & Jacuzzi - Orlando

Welcome to our stunning lakefront resort, where luxury meets tranquility! Dive into our expansive 100,000-gallon pool, enjoying a refreshing swim surrounded by breathtaking views. Inside, our tastefully designed space features midcentury modern amenities ensuring you have everything for a perfect getaway. Each bedroom offers serene views and plush bedding for a restful night’s sleep. Whether you seek adventure or relaxation, this is your ideal getaway. Book now for unforgettable memories!

4.92 out of 5 average rating, 119 reviews

10 min Disney | Lakeview Hot Tub, BBQ | Game Room

Welcome to your family's next dream vacation! You'll be located only 10 minutes from Disney, 20 minutes from SeaWorld, 25 minutes from Universal, and just 30 minutes from Orlando International Airport (times vary by traffic). When you want to unwind at the house, you have a fully loaded game room (billiards, air hockey, foosball, and more!), private swimming pool and hot tub with a breathtaking lake view, BBQ grill, ultrafast Wi-Fi, and complimentary Disney+ on each of the five 4K Smart TVs.

4.98 out of 5 average rating, 140 reviews

Villa in Kissimmee

Sleeps 20✦Free Pool Heat✦15 min to Disney✦Hot Tub

Make memories to last a lifetime in our luxurious 9-bedroom home (sleeps 20) at Orlando's premier vacation community. Enjoy your own Marvel game room, private pool (heated at no extra charge*), and hot tub. Our Five-Star rating from previous guests and our generous cancellation policy means you can book with confidence. Only 15 minutes to Disney and just a 3-minute walk to a fabulous resort clubhouse with free access to a lavish pool, kids waterpark, restaurant, playground, gym, and more!

4.97 out of 5 average rating, 111 reviews

Home in Four Corners

Dream Family Experience w/Star Wars & Lightyear Rm

Experience the magic of Disney World and the very best of Orlando from the comfort of this luxury private resort! Conveniently located in ChampionGate Resort Phase III, enjoy the the resort style amenities or explore the world class attractions in Orlando and Kissimmee. Minutes from Disney World, Universal Studios, Sea World, Premium Outlet Malls, and beyond! This modern retreat is focused on providing an unforgettable and exceptional family centric vacation experience!

5 out of 5 average rating, 226 reviews

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.

4.99 out of 5 average rating, 132 reviews

Home in Reunion

*Luxurious Paradise Mansion: Pool, Spa & Cinema

The perfect balance of STYLISH DESIGN, LUXURIOUS COMFORT, & ENDLESS ENTERTAINMENT in the stunning 3.5 square mile Reunion Resort. You will have your own private pool, spa, movie theater - game room, 3 master suites, 3 incredible themed bedrooms (MARVEL, FROZEN II, NASA) for kids or adults, the latest Xbox Series X game station, a 2500 ft2 pool deck overlooking a beautiful forest and pond, fire pit, & billiards table, minutes to Disney.

5 out of 5 average rating, 7 reviews

Sleeps 30 | 12BR Home | Custom Rooms

🏰 12BR Family Villa near Disney! Sleeps 30 | Private Pool, Spa, Themed Bedrooms, Game Room & Theater | Located in Veranda Palms Resort just 7 miles from Disney. Features include Avengers-style theater, fully equipped kitchen, kids' themed rooms (Star Wars, Frozen, Minions & more), 10 bathrooms, and spacious living/dining areas. Enjoy resort amenities: pool, splash pad, gym & playground. Perfect for large families or group getaways!

4.79 out of 5 average rating, 24 reviews

The Eights House by Disney. Themed Island Dream

Location can't get better! Next to Disney Parks and Restaurant Row! This Guarded and gated place to stay is perfect for family trips. You will fall in love with our year round 12ft tree tastefully decorated by season. Mickey's Camping room, Frozen themed room, the cabin Christmas year round experience & 2 additional modern king rooms perfect for couples! Did I mention the stunning Avengers Home theater/game room and oversized pool?