Vacation rentals with a pool in Osceola County

4.82 out of 5 average rating, 256 reviews

A private movie theater features a 150-inch screen displaying a Disney image. Black walls and hardwood flooring create a modern atmosphere. Comfortable reclining seats with cup holders are arranged for a cinematic experience, ensuring a cozy and immersive viewing environment.

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.

The villa features a modern exterior with a sloped roof and a two-car garage. Palm trees are landscaped around the front yard, which is bordered by well-maintained grass. A clear blue sky provides a bright backdrop to the welcoming entrance.

4.87 out of 5 average rating, 250 reviews

3 bedroom Villa in Kissimmee

The villa is in a residential area within a 5-min drive to local amenities including, a pharmacy, 3 supermarkets and 2 gas stations. The property is between 15 - 40 mins drive from Disney, Epic Universe, SeaWorld, Gatorland & Universal Studios. Orlando International Airport is only about 17 mins drive away. Osceola Heritage Park, the home of the world’s largest collector car auction is only 4 mins drive from the villa. The Florida Turnpike that runs through Miami is 6 mins from the property.

4.97 out of 5 average rating, 160 reviews

The exterior of the barn showcases a rustic wooden facade beneath a metal roof. A porch with seating options invites relaxation, while the neatly maintained yard features green grass and landscaping. A driveway leads to a side garage, enhancing the property's charm and accessibility.

Barn in St. Cloud

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

A private pool area features a crystal clear pool with a built-in spa, surrounded by a screened enclosure. A spacious patio is equipped with lounge chairs, a dining set, and a barbecue grill, offering a relaxed outdoor environment.

4.94 out of 5 average rating, 124 reviews

Vacation Home 3 bedroom/2 full bath/private pool

Bring the whole family to this great place with lots of room for fun. This house is perfect for you, your family, and friends! Spacious 3 bedrooms and 2 full baths that can accommodate up to 9 people. The house is fully air conditioned and has a pool. Indoor entertainment such as board games, ping pong table and TV cable. Please note smoking or parties are NOT allowed in house premises. No pool heater available during May through October. **You also MUST be 21 or older to rent this property**

5 out of 5 average rating, 115 reviews

A private pool area is showcased with a screened enclosure, featuring a clear, inviting pool surrounded by a stone deck. Comfortable outdoor furniture is set under a red umbrella, offering shade. The villa's exterior walls are visible, alongside large glass doors leading into the interior.

Villa in Kissimmee

Villa Sol Peaceful Pool/Hot tub Home

Close to all major attractions, and airport sits this private villa. It has a little something for all ages! Your family can play in the pool or relax in the hot tub. Enjoy fun game nights with the cabinet full of games, or play a little game of basketball right outside the pool. Enjoy the tennis courts and playground. Stay in shape while you travel just steps away from the clubhouse gym. There is everything for the beach trips or the ball games. All of your baby's needs are covered as well.

4.99 out of 5 average rating, 171 reviews

Cottage in Kissimmee

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!!

4.99 out of 5 average rating, 124 reviews

A private pool features a spacious deck and a whimsical swan float. Adjacent is a covered dining area with views of landscaped grounds. Inside, a kids’ tube slide and superhero-themed decor are seen, along with a game area featuring a billiards table and arcade console.

Villa in Osceola County

*Private Resort Oasis: Golf-Front, 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.

A living area features a modern television displaying a virtual fireplace, paired with elegant wall art and a decorative plant. Below, a pool area is illuminated with soft purple lighting against a backdrop of warm string lights, creating a relaxed atmosphere.

4.97 out of 5 average rating, 105 reviews

Modern House with Private Pool Getaway Kissimmee

This property is accommodated for families looking to vacation with peace of mind, the facilities are perfectly arranged so that you and your family feel at home. It has 3 rooms equipped for adults and children, the patio area is the perfect place to spend time with your family either in the pool or enjoying a barbecue on the grill.( POOL IS NOT HEATED) -No parties allowed in the house. No smoke. Do not park blocking the sidewalk, no park on the grass, nor in front of the neighbors' house.

Superhost

Home in Osceola County

4.93 out of 5 average rating, 121 reviews

Pirate & Princess: Themed/Disney/Resort

Wishes come true at The Pirate & Princess 5BR/6BA immersive vacation home, 6 miles from Disney. Seeking enchanted adventure? Sprinkle pixie dust, second star to the right, to… Reunion Resort! Gated golf resort; pools/dining/gym. Treasure Island, Peter Pan, Tinker Bell, Captain’s Lounge, Little Mermaid & Moana; Disney-inspired rooms, professionally designed! Private Pool/Spa/BBQ/Chef’s Kitchen/Office/Laundry/WiFi/In-Law Apt./Sunset Lake Views. Family-friendly gem to delight kids! Sleeps 15.

Superhost

Villa in Kissimmee

4.87 out of 5 average rating, 524 reviews

Magical 5-Bedroom Villa Near Universal's Wizarding

Ensure an enchanted holiday in Orlando. Inspired by everyone’s favorite castle, this magical home provides an immersive experience with 5 bedrooms, common room with large screen TV with Netflix & Nintendo Switch, dining hall, fully equipped kitchen, swimming pool, patio with grill and laundry room. Located in a quiet residential community, 10 miles to the Wizarding World of Harry Potter, 6 miles to Disney, 5 miles from Celebration, 4 miles from Old Town and 18 miles from downtown Orlando.

A single-story home is showcased with a light gray exterior and a dark garage door. Lush green grass surrounds the front, complemented by palm trees and shrubs. The driveway leads to the entrance, under a clear blue sky with a few clouds.

4.9 out of 5 average rating, 132 reviews

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!