Holiday rentals with a pool in Windsor Hills

An expansive game room features themed decor, including a vibrant mural of a surfboarder. The private pool area, enclosed with a screen, showcases a clear blue water surface surrounded by spacious lounge chairs. Aerial views of the community pool and water park amenities are also visible.

4.82 out of 5 average rating, 142 reviews

Magical Adv 5 Star Villa Movie Room Arcade Pool an

Experience enchantment at Magical Adventure Villa, a top-rated 6-bedroom and 4-bath home for 12 guests. Conveniently located in Windsor Hills Resort, just 2 miles from Disney World®. Experience the highly acclaimed getaway that has garnered rave reviews. Enjoy a private pool, home theater, and a thrilling arcade. Unleash your inner Jedi at the state-of-the-art Star Wars gaming center with a movie theater, Xbox One, Nintendo Switch, and immersive 3D designs. *Work vehicles are not permitted to b

The spacious living area features comfortable seating arrangements, large windows, and a decorative area rug. The view leads to the private screened-in pool, providing a seamless indoor-outdoor experience. The room is illuminated by natural light and complemented by a modern ceiling fan.

4.99 out of 5 average rating, 148 reviews

Game & Theater Room, Castle Bunks, Pool & Spa

Vacation at Windsor’s Best located in Windsor Hills Resort just 2 miles from Walt Disney World. This one-story 4 bed, 4 bath vacation villa has everything you need for a wonderful getaway with family or friends. Situated on an elevated corner lot, this spacious villa with it's private pool and spillover spa offers a beautiful view overlooking the resort community. Plus, guests have access to the family-friendly Windsor Hills Resort amenities, including the water park, playgrounds, gym and more.

4.92 out of 5 average rating, 160 reviews

New Luxury Condo near Disney

A passos da piscina e parque aquático. Covid-19 safe. Wi-fi de 500 megabytes! O apartamento possui localização privilegiada: está no condomínio fechado Windsor Hills, o mais próximo dos parques. A 10 minutos do Animal Kingdom, Epcot, Hollywood Studios e Magic Kingdom e a 25 minutos dos parques da Universal. Além disso, possui fácil acesso ao aeroporto (US 192, FL 417 e I-4), Downtown Orlando, Miami e a todos os atrativos da região da Central Flórida (Daytona Beach, Clearwater, St. Petersburg).

A home theater room is equipped with red stadium seating for eight, positioned toward a large screen displaying vibrant visuals. An arcade game machine is set beside the screen, with ambient blue lighting accentuating the dark walls, creating an engaging entertainment space.

4.86 out of 5 average rating, 140 reviews

Resort Home 3.5 miles to Disney with home theater

We welcome you to stay in our home located in the Windsor Hills community with a water park, slides, theatre and so much more! The house is just 3.5 miles from Disney’s Animal Kingdom. Our home has 6 large bedrooms including laundry in the home, an 8 seat home theatre, TVs in every room, a large swimming pool & spa with a large patio cover, plus a large kitchen fully equipped with everything you need for your stay. Please message us if you have any questions, we look forward to hosting you!

A bright living area features a comfortable brown sofa and loveseat, accented with decorative pillows. A modern coffee table is centered on tiles that enhance the spaciousness. Natural light filters through large windows, while a flat-screen TV is mounted on the wall, framed by stylish light curtains.

4.86 out of 5 average rating, 161 reviews

Star Wars Condo in Windsor Hills 3 bdrm, 2 baths

Welcome to our Star Wars themed rental in Kissimmee, FL, just 3 miles from Disney World! Experience the ultimate vacation in a galaxy far, far away. Located in Windsor Hills Resort with a heated community pool and two water slides. The kids bedroom has Star Wars decor, twin bunk beds, and an electronic pinball machine. The condo is decorated with Star Wars artwork and a half-sized Darth Vader figure. The kitchen is fully equipped. Don't miss this chance to live out your Star Wars fantasies.

An outdoor dining area features a large, custom-built farmhouse table surrounded by benches. Refreshments and fruit are displayed on the table, with a private pool visible in the background, enclosed by a screened lanai. Lush green grass complements the serene atmosphere.

4.96 out of 5 average rating, 223 reviews

★Completely Renovated★ 3 mi to Disney+Free Resort!

Closest FREE resort to Disney Parks! Sandpiper Shores is a 6 bedroom 4 bathroom luxury villa that sleeps 14. BEST STAR RATING - OVER 200 REVIEWS! * Kitchen is loaded & all baby gear provided. * Custom game room with A/C, LED panel lighting, & ROCK CLIMBING WALL! * Roku smart TVs & NEST tech throughout. * Outdoor space includes your own private pool, hot tub, overhead lighting, NEW grill, & 10' custom-built farmhouse table to seat the whole family! Every detail has been thought of!

A collage of vibrant images showcases the luxurious amenities available, featuring a spacious pool area, themed bedrooms, an arcade room, and outdoor seating. The photos capture a welcoming environment ideal for family gatherings and entertainment, beautifully arranged in a Mickey Mouse shape.

4.99 out of 5 average rating, 102 reviews

Cozy Themed Villa 6 BR | Close to Disney

🏖️☀️🏄‍♀️Stay just minutes from Disney in this spacious 6-bedroom home, perfect for a family getaway. It comfortably sleeps up to 14 guests and is designed for both kids and adults to enjoy. Located in Windsor Hills Resort — one of the closest communities to Disney World — you’ll have quick and easy access to the parks. Enjoy themed bedrooms, a game room, and your own private patio and pool — great for relaxing after a fun day at Disney.🌴👙🩳🥽🩴 ❤️❤️We'd love to welcome you here!

5 out of 5 average rating, 9 reviews

Themed 6BR | Game Room | Private Pool & Spa w/View

Stay at Time-Out Corner, Too @ Windsor Hills for an incredible vacation filled! Enjoy a game room, themed bedrooms, a private pool and spa w/gorgeous sunset view, and more. Plus, free access to the resort’s clubhouse and water park. Just 5 mins from Disney! 🎮Toy Story Game Room. Play Air Hockey, Skee-Ball, Arcades, Xbox, PlayStation, and more. 🏊 Private West-Facing Heated Pool/Spa. 🛏️ 6 BR & 4 BA. 3 Themed Bedrooms (UP, Alice in Wonderland, and Orange Bird). Sleeps 14.

A recreational game room is presented, featuring an air hockey table and a pool table centered in the space. Two gaming chairs are positioned near flat-screen monitors on the wall. Colorful LED lighting creates an engaging atmosphere in the room.

4.96 out of 5 average rating, 155 reviews

Mr. Clean's Cozy Disney Home w/ Luxury Finishes

• Newest house in the #1 resort community in the Disney Area, Windsor Hills • ALL Mattresses & Pillows are encased in waterproof SANITIZED covers. • 2 FUN children themed rooms (Star Wars, & Frozen) • Onsite, driveway parking for 3 vehicles • FREE pool heat + BBQ with ALL rentals • Fully equipped + stocked kitchen; including Keurig machine • Self check-in with digital lock • Super FAST Wi-Fi wireless internet speed at +1,000 Mbps!! • Property is managed directly by owner

A vibrant games room is equipped with various arcade machines, including SpongeBob Racing. A massage chair is positioned nearby, while a theater room features plush seating. An outdoor space highlights a screened-in pool area surrounded by palm trees, visible through large windows.

4.99 out of 5 average rating, 246 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.

A collage showcases various areas of Mickey's Star Wars Retreat. A spacious bedroom features a king-sized bed with blue accents. In another scene, a bright water park is viewed from above. An open kitchen with modern stools, a child's room with themed decor, and a cozy living area with a sectional sofa complete the visual narrative.

4.98 out of 5 average rating, 112 reviews

StarWars Theme + Free Waterpark | 10 min to Disney

Family-friendly Star Wars Retreat in Windsor Hills Resort — just 10 minutes from Walt Disney World! Enjoy a private screened splash pool, smart TVs in every room, fully equipped kitchen with fun themed touches, and FREE access to resort waterpark, lagoon pool, hot tub, arcade, playgrounds, and sports courts. Washer/Dryer in the home. Spacious, modern, and perfect for multigenerational stays or longer vacations.

A cozy living area is featured with comfortable seating, including a sleek sofa and stylish chairs. A contemporary fan hangs from the ceiling, while a wall-mounted TV is displayed above a dark cabinet. A dining area is set with a table and decorative plates, with views of the screened patio.

4.83 out of 5 average rating, 215 reviews

Fun, Sun, Theme Parks and More

Build lasting vacation memories and sleep in style just minutes from Disney World. Your family will be at home in this spacious 3 bedroom townhouse with its own private heated pool (no extra charge) and full kitchen. And when you're not at Disney, it's just a 5 minute walk to the clubhouse and FREE heated pool and water park at the fabulous Windsor Hills resort.

Popular amenities for Windsor Hills rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A collage of images showcases the villa's vibrant interiors and amenities. The staircase features colorful beach-themed decor. The open living area contains comfortable seating and artistic wall murals. Bedrooms are themed with playful elements, and the outdoor area features a private pool and spa surrounded by greenery.

4.96 out of 5 average rating, 26 reviews

Paradise Cove at Windsor Hills Resorts

A spacious two-story villa stands in a well-kept community, featuring a tile roof and decorative front door. Lush green landscaping surrounds the entrance, with neatly trimmed shrubs and grass. The driveway is clear and offers parking space for multiple vehicles.

4.77 out of 5 average rating, 35 reviews

6BR/5BA DisneyVilla, Pool+Spa, GameRoom, Clubhouse

A screened-in pool area features a clear blue pool with floatation devices, surrounded by a sunlit deck. A Tiki bar with seating stands to one side, while lounge chairs are arranged along the edge. Lush greenery is visible beyond the enclosure.

4.95 out of 5 average rating, 120 reviews

Disney Retreat | Huge Pool with Spa | 2 King beds

5 out of 5 average rating, 59 reviews

An inviting outdoor area showcases a private pool and spa, surrounded by lounge chairs and colorful beach balls. A dining table and large gas grill offer options for outdoor meals. Lush greenery lines the fence, providing privacy and a vibrant backdrop against a sunny sky.

Home in Four Corners

Gorgeous 5BR @ Encore Next to Disney - 305

4.96 out of 5 average rating, 49 reviews

Luxury 5BR, Pool, Theater & Game Room, Near Parks

The image showcases a colorful game room featuring themed decor, cozy lounging spots, and engaging game tables. A separate view displays a vibrant community water park with palm trees and pool areas. The combined images highlight the fun and relaxation available in the villa's surroundings.

4.9 out of 5 average rating, 68 reviews

ReDesigned | Windsor Hills | Location | Water Park

5 out of 5 average rating, 7 reviews

Themed Villa:10 min to Disney: Pool, Gameroom, BBQ

A spacious poolside dining area is featured, with a large table set for meals. Elegant place settings include green plates and silverware. A large screen is visible, showcasing outdoor entertainment, with colorful sunset hues reflecting through the screened enclosure.

4.94 out of 5 average rating, 80 reviews

8 Mins To Disney W/Poolside Theater & Games Room

Apartment rentals with a pool

A comfortable living room features a spacious sectional sofa adorned with decorative cushions. A large TV is mounted on the wall, displaying a serene landscape. Light enters through sliding glass doors, leading to a balcony, enhancing the room's bright ambiance.

4.78 out of 5 average rating, 212 reviews

Magic Stay at Windsor Hills! 2 bedroom apartment!

An inviting living space features a modern gray sofa centered around a round coffee table, set on a plush area rug adorned with a playful pattern. A wall-mounted fan circulates air beneath a vibrant Mickey Mouse artwork, while a dining table for four is positioned nearby.

4.93 out of 5 average rating, 183 reviews

🏖 Resort Condo | 🎢 2mi -> Disney | 💦 Waterpark Fun

A vibrant outdoor water park is depicted, featuring two large water slides and a colorful kids' splash area. Surrounding palm trees provide shade, and a spacious pool area is visible in the background, inviting relaxation and fun.

4.91 out of 5 average rating, 225 reviews

Disney's Doorstep, 3 Bed 2 Bath, Waterslides!

4.82 out of 5 average rating, 312 reviews

Beautiful 2/2 Gem, 2 mi to Disney with Water Park!

The exterior of the Westgate Vacation Villas showcases an elegantly designed building with multiple levels. Soft lighting from street lamps illuminates the entrance. Rows of golf carts are parked in front, surrounded by manicured landscaping and palm trees under a clear blue sky.

4.86 out of 5 average rating, 335 reviews

Westgate Vacation Villas - 1 Bedroom

A spacious pool area is featured, surrounded by palm trees and lounge chairs. The expansive waterpark includes vibrant waterslides, providing a lively atmosphere. A relaxing hot tub is also visible nearby, complemented by a well-maintained landscaping that enhances the resort's inviting ambiance.

4.98 out of 5 average rating, 191 reviews

Poolside 3Br Windsor Hills, Disney 2mi, Waterpark

A vibrant pool area is depicted, featuring colorful water slides and various water play structures. Nearby, a spacious balcony can be seen with outdoor furniture, offering views of the resort. Inside, a cozy living area includes a children's play table, while a bright theme room showcases colorful wall art inspired by Disney.

4.8 out of 5 average rating, 142 reviews

Charming Windsor Hills Condo Near Disney Parks

An aerial view showcases a resort-style pool surrounded by lounge chairs. A colorful water park with slides is located nearby, complemented by lush greenery and palm trees. Multiple buildings are visible in the background, offering a welcoming atmosphere for families.

4.85 out of 5 average rating, 187 reviews

WH Condo. Pool/Waterpark and close to Disney!

Other holiday rentals with a pool

5 out of 5 average rating, 11 reviews

The Disney House • Immersive Rooms • Gaming Lounge

A landscaped resort area is showcased, featuring a large swimming pool that reflects the evening sky. Surrounding palm trees and well-maintained greenery create a serene environment. The elegant clubhouse is visible in the background, inviting guests to explore the amenities.

4.88 out of 5 average rating, 94 reviews

Relaxing Vacation Resort Villa

A spacious two-story villa is surrounded by a manicured lawn and tropical landscaping. A paved driveway leads up to the entrance, framed by palm trees and vibrant greenery. The exterior features a light-colored stucco finish and a welcoming front porch.

4.89 out of 5 average rating, 18 reviews

5BD Formosa Gardens Near Disney (FG 7939)

5 out of 5 average rating, 76 reviews

3 Miles 2 Disney | DisneyThemed | Fully Renovated

4.89 out of 5 average rating, 18 reviews

An outdoor area showcases a private pool surrounded by sun loungers, with views of a golf course in the background. The pool's rippling water reflects the clear sky, complementing the serene atmosphere.

Villa in Four Corners

Amazing New Villa! Well Maintained! Fun for all!

An outdoor dining area is presented under a screened enclosure, featuring a wooden table with seating for eight. A movie screen displays a scene from Disney Moana. The surrounding pool area includes lounge chairs, with vibrant colors reflecting in the evening sky.

5 out of 5 average rating, 27 reviews

Luxe Windsor Hills w/Poolside Theatre & GameRoom

A welcoming entryway is highlighted by a wooden staircase with white railing and a decorative mural on the wall. A green velvet bench sits beside a woven basket. A vibrant neon sign reads 'The happiest place on earth,' adding a cheerful touch to the space.

5 out of 5 average rating, 16 reviews

Elegant Disney Themes | Pool, Hot Tub & Game Room

A children's suite hosts a whimsical treehouse-themed bunk bed with a slide, shaded by mural-painted trees. Soft green carpet covers the floor, and a plush gray sofa is positioned nearby. A stuffed Winnie the Pooh character adds a playful touch to the setting.