Villa holiday rentals in Windsor Hills

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.

4.82 out of 5 average rating, 275 reviews

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.

A themed game room showcases a Batman-inspired design with a bright yellow slide leading to a two-level play area. An air hockey table is positioned prominently, surrounded by stylized dark walls, creating an immersive gaming environment.

4.99 out of 5 average rating, 137 reviews

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!

An inviting outdoor pool area is featured, surrounded by a protective screen enclosure. The pool water is a clear turquoise, reflecting the evening sky. Comfortable seating is arranged nearby, alongside a BBQ grill. Soft lighting enhances the tranquil atmosphere.

4.94 out of 5 average rating, 123 reviews

❤NEW Gorgeous 5br/3.5ba|POOL| Game ROOM| Disney

Nestled in the peaceful 4 Corners community close to Disney & top rated attractions, Target, Publix & restaurants. Newly updated, inviting and modern 2 level, 5 bedroom/3.5 bath with comfortable luxurious beds! Equipped with a private pool (heat for an extra fee), game room, BBQ grill & free Nespresso. Out back is a mini golf putting green, corn hole and fire pit for the family to gather around under the warm vibe of string lights. A place for the family to retreat, relax, reset and have fun!

An outdoor dining area features a large, custom-built wooden table surrounded by black chairs. Blue plates and glassware are meticulously arranged for an inviting meal. A bright blue pool glimmers in the background, enclosed by a mesh screen to ensure privacy.

4.97 out of 5 average rating, 141 reviews

*Brand New!* Minutes to Disney + Free Resort!

Closest FREE resort to Disney Parks! Hibiscus Hideaway is a 6 bedroom 4 bathroom luxury villa that sleeps 14. Completely renovated in October 2022! * Kitchen is loaded & all baby gear provided. * Custom game room with A/C, LED panel lighting & ROCK CLIMBING WALL! * New Roku smart TVs & NEST tech throughout. * Outdoor space includes your own private pool, hot tub, overhead lighting, NEW BBQ grill & 10' custom-built farmhouse table to seat the whole family! Every detail has been thought of!

4.99 out of 5 average rating, 133 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.

The exterior of a two-story home is showcased, featuring a well-manicured lawn and palm trees in the front yard. A spacious driveway leads to a garage with a white door, while the house displays a neutral color scheme and large windows allowing natural light.

4.93 out of 5 average rating, 107 reviews

Disney Dream Villa- 10 Minutes From Disney!

Get ready for the home of your dreams! Disney Villa is a spacious 5 bedroom, 3.5 bathroom home that is inspired by the magic of Disney, and is about 10 minutes from the parks! This home sleeps a whopping 10 people, perfect for large families! The home also has a living room, dining room, full kitchen, a game room, laundry area, and a private pool and lanai area. Guests have access to Windsor Palms' many on-site amenities. If you're looking to be close to the magic, this is the home for you!

Villa in Championsgate Village

A vibrant game room displays an air hockey table and foosball station, with colorful LED lights casting an engaging glow. An adjoining indoor theater features plush seating and a large screen, while a private pool area invites relaxation, surrounded by lush greenery and floatation devices.

4.97 out of 5 average rating, 102 reviews

Pool Movies|Water Park|Movie Theater|Arcade|Themed

Enjoy our Early Bird Sale and Save! ✨ Discover an enchanting escape at Ice Saber Manor-a stunning 6 bed Villa featuring FROZEN and SPIDER-MAN rooms, 4 gorgeous master suites and endless entertainment options! Immerse yourself in cinematic wonders with a Star Wars MOVIE THEATER, belt out your favorites in the KARAOKE area or revel in our POOLSIDE THEATER! Relax in your heated POOL&SPA or enjoy our WATERPARK! Discover Disney from the comfort of this modern home nestled in a beautiful resort!

The outdoor living space features a cozy seating area surrounding a fire pit and a large dining table. A private swimming pool is illuminated in blue, with sun loungers lining the edge. The backyard is framed by palm trees, creating a tropical ambiance at dusk.

5 out of 5 average rating, 113 reviews

8 BR Villa, Private Pool, Theater, Min to Disney!

Big and Beautiful Themed Vacation Villa in premium gated Encore Resort. Spacious main floor for entertaining large groups - bring the family and friends! Enjoy the included resort amenities a minute's walk from the front door. Or, relax around your private pool and custom summer kitchen. Enjoy big-screen movies and sound in the theater in premium loungers, and play classic arcade games! min from Disney, one of the closest villa resorts. Tons of shopping and dining nearby!

The image showcases a vibrant collage of the villa's features. The top left displays a colorful Encanto-themed bedroom with a playful bed. The top right features the modern living area with large windows and comfortable seating. The bottom left presents a private pool area, and the bottom right highlights a Mario-themed game room with arcade games.

4.98 out of 5 average rating, 124 reviews

Magical 5BR Family Vacation Villa

Professional Hosts & Guest Favorite Home! Immaculate and well equipped Stargazer Villas vacation home at Windsor Island Resort now featuring Pickleball Court! This central Florida villa has heated pool included for your family to relax in after a busy day at the parks. Family friendly, featuring Star Wars, Harry Potter, & Encanto themed bedrooms, and a new Mario World game room! Stargazer Villas provides the perfect place to create unforgettable memories with your family.

A vibrant collage highlights the Tiki Tropical Oasis. The inviting pool is surrounded by lounge chairs under umbrellas. A colorful putting green and BBQ grill add to the outdoor appeal. The interior features thematic rooms, showcasing tropical decor and immersive environments designed for family enjoyment.

4.99 out of 5 average rating, 112 reviews

OMG Private Pool Oasis! LED Lights! Mini Golf!

This is the place! Look no further for the most magical immersive dream vacay! Welcome to your own private tropical paradise oasis minutes from Disney World! In Encore Resort by Reunion (gated community) enjoy your private pool, hot tub/jacuzzi, hammock swings, tiki bar, unique mini golf experience. The LED lighting in the backyard & throughout the house will wow you! Gorgeous decor and immersive themed rooms for the kids! The perfect place for your dream family vacation!

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, 148 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 private pool area is enclosed by a protective screen, showcasing clear turquoise water. Lush palm trees are visible in the background, providing a tropical ambiance, while the surrounding patio features lounge chairs for relaxation. A spacious outdoor environment invites leisure and enjoyment.

4.76 out of 5 average rating, 235 reviews

Feel the Magic: 9 min Disney • Pool • Pet • Relax

✨ Looking for comfort, privacy, and fun near Disney? Our pet-friendly home is ready to welcome your family — including your furry friend — for amazing days under the Florida sun. Magic Kings House invites you to create magical moments with your loved ones, offering comfort and exclusivity at Windsor Palms, the resort most loved by guests. Every detail has been carefully prepared to make your vacation easy, relaxing, and filled with wonderful memories. 🌴🐶☀️

Popular amenities for villa rentals in Windsor Hills

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Private villa rentals

The exterior of a two-story home is shown, featuring a light-colored façade with large windows. A vehicle is parked in the driveway, and green shrubs and a magnolia tree are visible in the well-maintained yard. Clear blue skies provide a bright backdrop.

4.86 out of 5 average rating, 29 reviews

3 Miles from Disney 5/5 Pool home-free pool heat

A single-story home features a prominent entrance with arched windows and a welcoming front door. Lush green landscaping surrounds the property, while palm trees sway gently in the foreground. A two-car garage is visible, set against a backdrop of blue skies and puffy clouds.

4.93 out of 5 average rating, 123 reviews

Themed Resort Villa | Pool | Spa | Mins to Disney

An outdoor view of a screened private pool area shows a refreshing pool surrounded by lounge chairs, with a tranquil landscape in the background. The enclosed space provides interruption-free relaxation.

4.7 out of 5 average rating, 20 reviews

Funtastic Villa 6br4ba,pool, sleeps 14-Near Disney

The living area features a contemporary design with high ceilings, light-colored walls, and large windows providing access to natural light. A sectional sofa faces a modern entertainment unit with a television. Stylish hanging light fixtures create ambiance, while artwork adorns one wall.

4.96 out of 5 average rating, 24 reviews

4 Suites Villa near Disney+ Hot Tub@ Magic Village

4.81 out of 5 average rating, 26 reviews

Amazing home 5 mins to Disney Orlando

A game room features various entertainment options, including a treadmill, exercise bike, and classic arcade machines. The decor showcases a 'Star Wars' theme with vibrant blue lighting and dark walls, creating an inviting atmosphere for guests to enjoy recreational activities.

4.95 out of 5 average rating, 96 reviews

Luxury Villa! /Game Room/ Pool Heater

5 out of 5 average rating, 14 reviews

Lavish 11BD TrackMan Golf Pool Theater Disney EV

A spacious resort pool area is surrounded by palm trees, featuring a large pool with lounge chairs and umbrellas. A water slide and children's play area are visible in the background, while a building with a sloped roof provides amenities and shade to guests.

4.88 out of 5 average rating, 56 reviews

*Pet Friendly* Free Pool Heat - Windsor Hills

Luxury villa rentals

A vibrant game room inspired by space features several gaming options, including a foosball table, air hockey table, and arcade machines. The room is illuminated with blue LED lighting, and large screens are arranged for gaming, all set against a backdrop of starry wall designs.

4.99 out of 5 average rating, 76 reviews

Free Pool Heat & BBQ|Disney Nearby|Resort|Waffles

5 out of 5 average rating, 3 reviews

The Keys Villa

The themed bedroom showcases a king-sized bed adorned with a textured teal coverlet. A large AT-AT mural in the background complements the vibrant blue walls depicting a tropical Star Wars landscape. Two green and patterned pillows add a playful touch to the bedding.

4.71 out of 5 average rating, 14 reviews

BEST HOUSE! StarWars, HPotter, Princesses, Pirates

A spacious dining area features a long glass table surrounded by white chairs, set for a large meal with blue and gold accents. A striking blue wall with geometric gold patterns creates a modern backdrop, while contemporary light fixtures illuminate the space.

4.94 out of 5 average rating, 111 reviews

Blue Paradise 15BR 11BA, Sleeps 36, Theater/GameRm

A spacious living area is presented with a comfortable sectional sofa adorned with various cushions. A large, circular coffee table sits atop a soft rug, while a vibrant mural featuring a sunset over hills acts as a striking backdrop. Warm orange curtains frame the windows, enhancing the inviting ambiance.

4.9 out of 5 average rating, 113 reviews

3mi to Disney Star Wars Galaxy Edge 7BDRM Villa

4.87 out of 5 average rating, 152 reviews

Premium 6BR | Theater, Games & Heated Pool

A vibrant themed room showcases a blue slide and bunk beds, enhancing playfulness. Adjacent, a cozy bedroom features rich curtains and themed decor. A home theater room displays a large projector screen and comfortable seating. The private pool area is highlighted with seating, a projector, and colorful inflatables.

4.97 out of 5 average rating, 117 reviews

Pickleball PoolsideMovies |WalkToWaterpark| Arcade

4.87 out of 5 average rating, 63 reviews

11 Bedroom Sleep 30 Splash Pad Near Disney Hot Tub

Villa rentals with a pool

A private pool area is enclosed with a screen, revealing a sparkling pool surrounded by lounge chairs. The living room features comfortable seating arranged around a coffee table, complemented by large windows. An entertainment area showcases arcade games and a race car setup, while a hot tub offers a spot for relaxation.

4.91 out of 5 average rating, 56 reviews

Next Door to Disney • Pool • Arcade • Themed Rooms

The exterior of a single-story home is presented, featuring a light brown facade and white trim. A welcoming front door is centered beneath an arched window. Lush, green landscaping surrounds the entrance, while a driveway leads to a two-car garage. The sky is partly cloudy, enhancing the overall brightness.

4.85 out of 5 average rating, 52 reviews

Private House Close to Disney World, Big Pool

5 out of 5 average rating, 10 reviews

Casita Kissimmee!Family Vacation Villa! 8minDisney

A spacious living room features a large sectional sofa facing a flat-screen television. An elephant artwork adorns the wall, and natural light filters in through expansive sliding glass doors, leading to an outdoor seating area. A neutral color palette complements the wooden flooring.

4.78 out of 5 average rating, 146 reviews

Amazing pool house - 10 MIN FROM DISNEY ORLANDO

The game room features a pool table at the center, surrounded by a raised seating area and an arcade game cabinet. Dark blue and red walls complement the stylish decor, with art displayed on the walls. A flat-screen TV is mounted for entertainment.

5 out of 5 average rating, 4 reviews

6BD/4BA | Private Pool | Avengers Game Room

A private pool area features a heated pool and spa, surrounded by a screened enclosure. Colorful lounge chairs are positioned near the poolside, offering a relaxing space. A shaded dining set is visible, enhancing the outdoor experience in the sunny setting.

4.87 out of 5 average rating, 75 reviews

Luxury 4BR Getaway w/ Pool, Spa & Game Room

5 out of 5 average rating, 20 reviews

WaterView 4 miles to Disney 3Br 2Ba Pool Home

The open living area features high ceilings, large windows, and a cozy seating arrangement with a sofa and armchairs. Decorative wall art and plants enhance the design, while an elegant dining space and modern kitchen are visible in the background.