Villa holiday rentals in Windsor Hills

A private pool is framed by a screened enclosure, featuring a gentle waterfall and bordered by comfortable lounge chairs. The serene lake view is visible beyond the pool, complemented by lush greenery lining the shore.

4.86 out of 5 average rating, 198 reviews

Near Disney Gated LakeView Pvt Heated Pool

LIMITED PROMOTION! FREE CLEANING FOR BOOKING 2 WKS OR MORE! LOWEST CLEANING FEE! Military dscnts. New Pool Heatr, Dolby ATMOS, 65" LED TV w/ Airplay. Remote office setup. Sunset Lakes a secure gated comnty ~12 min from Disney & other parks. Villa offers Lake View pvt pool, gorgeous sunset, Playroom, Fishing dock. Fully furnished, sparkling clean w/ 5 bds - 1 King, 2 Qns, 2 Twin beds w/ 3 baths, kitchen & lndry. Come & enjoy your next trip to Disney & leave everything to a fantastic experience!

4.97 out of 5 average rating, 114 reviews

Stunning 7BR Resort Villa Free Spa & Pool Heat

Expansive7BR Stargazer Villas Orlando area vacation home is close to Disney World & includes complimentary heated pool & spa. Within the gated community of Solara Resort, enjoy fantastic amenities like the wave simulator, water park, fitness center, sports courts, and dining. Perfect for memorable family adventures our renovated modern design villa ensures each day is filled with joy, comfort, and unforgettable memories in the heart of Florida's magic, creating the ultimate vacation experience.

An outdoor dining area features a large custom-built farmhouse table surrounded by seating options. Flower arrangements are placed on the table, and a blue pool is visible in the background. The space is sheltered with a screen enclosure, allowing for a spacious view of the yard.

4.95 out of 5 average rating, 178 reviews

★Completely New★ 3 miles to Disney + Free Resort!

Closest FREE resort to Disney Parks! Plumeria Place is a 6 bedroom 4 bathroom luxury villa that sleeps 14. Completely renovated in March 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 & 9' custom-built farmhouse table to seat the whole family! Every detail has been thought of!

A spacious themed room is depicted, featuring an imaginative design with a dark, cosmic ceiling. The room includes a large blue slide and a staircase, adjacent to cozy bean bag chairs for seating. Colorful space-themed murals enhance the playful atmosphere.

4.98 out of 5 average rating, 122 reviews

4mi to Disney | Games | Private Pool

Get ready to make memories of a lifetime just over 3 miles to Disney when you stay at this newly renovated Star Wars and Lego-themed private pool villa. Located in Formosa Gardens Estates, a prestigious gated community, our home is professionally furnished with multigenerational families in mind and can comfortably sleep up to 15 guests. After a trip to the parks, enjoy a refreshing dip in the private pool and rest those tired feet in the spa (pool heat included in stays after 10 Dec 2025!).

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, 130 reviews

Themed Resort Villa | Pool | Spa | Mins to Disney

The Magic Escape – a luxurious 4-bedroom, 3-bath home in the gated Windsor Palms resort, known for its cleanliness and thematic allure. Just a short drive from Disney World, this retreat has two master suites with en-suite bathrooms, a Mickey Mouse themed bedroom, and a Harry Potter themed bedroom. Enjoy a private, air-conditioned Star Wars movie theater and Marvel game room with shuffleboard and foosball. The private pool and spa, under an enclosed lanai, ensure your privacy and relaxation.

4.99 out of 5 average rating, 136 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 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.

4.89 out of 5 average rating, 127 reviews

3mi to Disney Star Wars Galaxy Edge 7BDRM Villa

Embark on a galactic adventure in our Star Wars-themed 7-bedroom, 4.5-bathroom villa just 3 miles to Disney. Close to Celebration, Old Town & downtown Orlando, this retreat features a fully equipped kitchen, private pool & patio. Each room transports you to iconic Star Wars locations like Tatooine, Mos Eisley Cantina, Jabba's Palace, Dagobah, Death Star, Coruscant, Millennium Falcon & Bespin. The community offers resort amenities including pools, trails, gym, mini golf, tennis & basketball.

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, 107 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!

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, 150 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 surrounded by a screened enclosure, featuring a jacuzzi spa and lounge chairs. The pool is inviting, with light blue water reflecting the sky's pink and purple hues. A serene lake is visible beyond the pool, adding to the tranquil setting.

4.91 out of 5 average rating, 249 reviews

House by the Mouse: Something for Everyone!

Welcome to our completely remodeled solar four bedroom, three bath villa, less then four miles to Disney World, and only a short drive to Universal, Sea World, Lego Land, and other local attractions. Designed themed bedrooms include Harry Potter, Mickey and Minnie Mouse, Star Wars, and a romantic master bedroom that allows you to relax in comfort. The pool, spa, and the entire villa is just for you, no need to share with anyone else, so kick back and enjoy!

An overview of luxury amenities includes a vibrant water park with slides, a spacious pool surrounded by palm trees, and a modern game room featuring foosball and striking wall art. Nearby, a tranquil bedroom setup and an inviting private pool are also highlighted.

4.98 out of 5 average rating, 105 reviews

Luxury Villa in Windsor Hills Resort, 2 miles / 5

4 bed and 4 bath LUXURY VILLA located in the top rated WINDSOR HILLS RESORT, just 2 MILES / 5 MINUTES AWAY from Walt Disney World This Villa is newly renovated, immaculately clean, and has all you need for a fun and comfortable vacation. The Villa offers the ultimate game room, outdoor dinning, and a screened private pool & spa. All guests also have access to resort amenities. Lots of entertainment for all. * Security Deposit Required with reservation

A private screened patio features a heated swimming pool and a Jacuzzi surrounded by a spacious deck. Outdoor seating is provided, with a dining table and lounge chairs positioned for relaxation. Sunlight glimmers on the water, creating a serene atmosphere.

4.92 out of 5 average rating, 123 reviews

Gorgeous 3 bed, 2 bath villa w/ pool and jacuzzi

Gorgeous 3 bedroom, 2-bathroom villa set on a 1/4 acre of land, with our own screened, private, heated swimming pool & Jacuzzi, and high speed internet. Situated in a quiet residential community on the sought after Sunridge Woods in Davenport, only 9 miles from Disney. 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**

Popular amenities for villa rentals in Windsor Hills

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Private villa rentals

4.9 out of 5 average rating, 72 reviews

4 Miles to Disney - Pretty In Pink

A private theater is presented with six reclining seats, arranged in rows facing a large 155-inch screen. The room is accented by dark walls and illuminated with blue lighting, enhancing the cinematic atmosphere. Movie posters adorn the walls, contributing to the entertainment theme.

4.94 out of 5 average rating, 52 reviews

Disney Fun Time 8BD 4K Movie Theater Jacuzzi Pool

Superhost

An aerial view showcases the spacious house surrounded by well-maintained lawns and vibrant greenery. A tranquil lake can be seen at the rear, reflecting the clear blue sky. Nearby homes contribute to a charming residential atmosphere.

Villa in Four Corners

4.78 out of 5 average rating, 18 reviews

Fabulous 4 bed South facing Lake view near Disney

4.83 out of 5 average rating, 18 reviews

Mickey's Backyard Themed 6BR with Pool

A private pool and hot tub are surrounded by a screened enclosure, showcasing crystal-clear water. Comfortable lounge chairs are positioned along the edge of the pool deck, with large glass doors offering views of the adjoining living spaces. The sky displays soft colors of twilight.

4.94 out of 5 average rating, 49 reviews

Rest & Relax at Sunset by the Lake with SPA!

The image showcases a bright living area featuring a colorfully themed Mickey blanket draped over a spacious bed. A view of the outdoor pool and hot tub area is visible through a large window, with dining space in the background, highlighting seating arrangements and decor.

4.96 out of 5 average rating, 85 reviews

Disney, Pool, Hot Tub, Gym!

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.

4.98 out of 5 average rating, 91 reviews

The Balmoral Manor: Luxurious & Bright 5BR Oasis

The image highlights a private pool area featuring a sparkling blue pool surrounded by a screened enclosure. Comfortable lounge chairs are positioned nearby, and a relaxing spa is integrated into the design. A vibrant game room with themed decor and a pool table is also included, providing entertainment options.

4.97 out of 5 average rating, 33 reviews

Luxurious home 2 miles from Disney - Windsor Hills

Luxury villa rentals

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, 114 reviews

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

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.

4.98 out of 5 average rating, 123 reviews

Poolside Movies | 3Min.Walk to Waterpark| Game Roo

An interactive stage area is presented, featuring musical instruments including an electronic drum set and keyboard. A large mural of a guitar and palm trees creates a vibrant backdrop. The space is equipped with seating and surrounded by a lush green carpet.

4.97 out of 5 average rating, 116 reviews

Luxury Villa/15min2parks/Lakeview/Vgames/Theater

A private pool area is illuminated in a soft green hue, surrounded by a screened enclosure. Comfortable lounge chairs are positioned nearby, with a table set under an umbrella. String lights create a warm ambiance as the evening sky darkens.

4.99 out of 5 average rating, 141 reviews

Magical Disney House-Pool & Hot Tub,Free Waterpark

Villa in Championsgate Village

An imaginative arcade and themed play area is displayed, featuring a blue slide and space-themed bunk beds. A princess-themed room with a carriage bed is highlighted. An arcade area with vintage game machines completes the vibrant layout, showcasing a unique blend of fantasy and entertainment.

4.93 out of 5 average rating, 182 reviews

Free Pool Heat! Disney Themes, Arcade, Sleeps 22

A Star Wars-themed game room is featured, complete with multiple screens displaying iconic scenes. An air hockey table and foosball setup are visible, alongside gaming chairs arranged for comfortable seating. The room is brightly lit, emphasizing the vibrant decor that adds to the entertainment atmosphere.

4.96 out of 5 average rating, 185 reviews

Sleeps 24✦Free Pool Heat✦15 min to Disney✦Hot Tub

4.92 out of 5 average rating, 125 reviews

Storey Lake•9BR•Fire Pit•Pool•Hot Tub•Game•EV

4.97 out of 5 average rating, 120 reviews

Luxury Themed Villa 9 BR | Close to Disney

Villa rentals with a pool

A spacious living room features high ceilings and large windows that allow natural light to fill the area. Comfortable seating arrangements include a gray sectional sofa and two blue accent chairs. The open layout leads to a modern kitchen visible in the background.

4.86 out of 5 average rating, 51 reviews

Fun & Vibrant 5BD/5BA w/ FREE Resort Access!

5 out of 5 average rating, 13 reviews

Casita Kissimmee!Family Vacation Villa! 8minDisney

The outdoor pool area features a spacious swimming pool with a spa, surrounded by paved decking. Lounge chairs are arranged around the pool, while a colorful float and a hammock invite relaxation. Palm trees line the background against a vibrant sky.

4.95 out of 5 average rating, 60 reviews

Luxury 8BD Theater Game Pool Golf Firepit - Disney

A single-story residence features a neat brick driveway leading to a two-car garage. Lush green landscaping includes palm trees and colorful plants, enhancing the curb appeal. The front porch is inviting, with symmetrical windows framing the entrance under a gently sloped roof.

4.93 out of 5 average rating, 74 reviews

Luxury 4 Bedrooms, 3.5 Bathrooms with pool.

A two-story villa is presented with a tiled roof and a welcoming front entrance. Lush greenery and flowering plants enhance the manicured lawn, while a spacious driveway leads to a two-car garage. Clear skies provide a bright backdrop to the home's inviting façade.

4.88 out of 5 average rating, 26 reviews

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

5 out of 5 average rating, 6 reviews

Villa w/ Pool, Game Room, Hot Tub, Near Disney!

The pool deck features a spacious swimming pool surrounded by a screened enclosure. Four sun loungers are positioned nearby, accompanied by a cantilevered umbrella for shade. The tranquil conservation area is visible in the background, providing a peaceful setting.

4.98 out of 5 average rating, 53 reviews

Beautiful 4 bedrooms with South/West facing pool