Villa vacation rentals in Windsor Hills

A private pool area is enclosed by a screen, showcasing clear waters reflecting the sky. A colorful inflatable float adds a playful touch beside a grassy landscape and glimmering water beyond. Sunlight bathes the scene, enhancing the tranquil atmosphere.

4.94 out of 5 average rating, 203 reviews

3mi to Disney Heated Pool Arcade Villa Sleeps 10

Relax and enjoy a peaceful vacation with family and friends at our beautiful home only 3 miles from Disney World. Our newly renovated game room is equipped with 4 Arcade Machines, Pool Table & Air Hockey. Enjoy the private pool and a fully equipped kitchen. Just recently upgraded smart home with smart color LED lights throughout. Our community is the closest to Disney and other theme parks. We are located 6 mins from attractions, dining & shopping. Spa/sauna avail @ clubhouse Just renovated pool

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!

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, 182 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 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, 131 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, 137 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 private pool is surrounded by a screened enclosure, reflecting the bright blue sky. Two lounge chairs are positioned near the pool, with light-colored walls and large glass doors providing views of the backyard. A clock is mounted on the wall, indicating the time.

4.91 out of 5 average rating, 111 reviews

Lakeside Villa, Sunny Pool Deck, 10Min From Disney

At this peaceful and centrally-located place you will wake up with a lake view, a private pool, and beautiful spacious clean space. You will be in a gated community complete with community pool and playground. This home facing south so you can sun bathing all day. You'll be minutes away from majors theme parks. Such as; Walt Disney World, Universal Studios/Islands of Adventure, Sea World, Legoland/Cypress Gardens, Discovery Cove, Cape Canaveral, and more. This can be you home away from home.

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 private pool deck is enclosed with mesh, providing a clear view of the surrounding greenery. Two comfortable loungers are arranged beside the inviting swimming pool, adorned with orange striped towels. The peaceful outdoor space is well-lit by natural sunlight.

4.87 out of 5 average rating, 126 reviews

Sunny Family Retreat ~ Peaceful Pool ~ Game Room

Unwind in this sunny 4 Bedroom 3 Bath house nestled in a serene family-friendly neighborhood. This prime location allows quick access to nearby restaurants and shops while being just a short drive away from Disney World, Universal, Legoland, and more. The lively pool deck and entertaining game room offer various relaxing and fun amenities. ✔ 4 Comfortable Bedrooms ✔ 3 Large Bathrooms ✔ Fully Equipped Kitchen ✔ Swimming Pool ✔ Game Room ✔ Six TVs w/ Roku ✔ Sun Loungers Learn more below!

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, 120 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, 151 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

The image showcases a private outdoor pool with a screened enclosure, surrounded by lush greenery. A cozy children's bedroom features themed bedding with characters from popular movies. A spacious master bedroom is highlighted with a view of the pool through large glass doors. An overhead shot reveals the entire property set within a landscaped community.

4.97 out of 5 average rating, 116 reviews

Private South Pool & Nature View | 10m to Disney

Free pool heat! You and your family will absolutely fall in love with this stunning 4 bedroom 3 bathroom pool home backing onto a beautiful forest for complete privacy. The home is centrally located in the wonderful gated community of Sunset Lakes just a short drive from all of Orlando's world famous attractions! Disney World (4.7 miles), Sea World (13.2 miles), Universal Studios Florida, (18 miles). Not to mention dozens of fabulous restaurants within minutes!

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.

4.78 out of 5 average rating, 240 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 Windsor Hills villa rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Private villa rentals

5 out of 5 average rating, 14 reviews

Casita Kissimmee!Family Vacation Villa! 8minDisney

The exterior of a single-story home is presented, featuring a paved driveway leading to a two-car garage. Lush green grass surrounds the house, and palm trees are positioned near the entrance. A colorful sunset sky provides a picturesque backdrop.

4.99 out of 5 average rating, 143 reviews

Beautiful home. Private pool. Close to Disney!

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.

4.95 out of 5 average rating, 55 reviews

Disney Fun Time 8BD 4K Movie Theater Jacuzzi Pool

Superhost

A private pool area is enclosed with a screen, featuring a clear blue pool surrounded by lounge chairs. A dining table is positioned nearby, with green landscaping visible in the background. The expansive sky above is bright and clear, enhancing the outdoor leisure space.

4.67 out of 5 average rating, 150 reviews

Villa w/ Pvt Pool & BBQ + Resort | 10 min Disney

A private pool is enclosed by a screened lanai, featuring clear blue water inviting relaxation. Lounge chairs in aqua blue are positioned along the edge. The surrounding green landscape is visible through the screens, providing a serene outdoor setting.

4.88 out of 5 average rating, 81 reviews

Elegant 4BR Retreat w/ Pool & Spa

Superhost

4.82 out of 5 average rating, 11 reviews

Disney Family Villa – Pool, Hot Tub & Game Room!

A heated swimming pool is enclosed by screen protection, providing a clear view of the water. Surrounding greenery adds privacy, while a patio area features sun loungers and a grill for outdoor dining. Sunlight reflects off the water, creating a bright atmosphere.

4.84 out of 5 average rating, 51 reviews

South facing Modern villa in quiet gated estate

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

Luxury villa rentals

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

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, 116 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, 125 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

4.93 out of 5 average rating, 135 reviews

A spacious living area features a sectional sofa in deep blue, complemented by two stylish armchairs. A wooden coffee table sits in the center, surrounded by a soft area rug. Natural light fills the room through large windows, enhancing the modern décor.

Villa in Four Corners

House Majestic, Luxury Villa 6b/5b near Disneyland

4.97 out of 5 average rating, 112 reviews

A private pool is framed by a stone patio, with lounge chairs positioned nearby for relaxation. Lush greenery and palm trees surround the area, creating a serene outdoor environment. A spa is positioned next to the pool, providing an inviting space for relaxation.

Villa in Four Corners

The Golden Bear Villa | Private Pool & Theater

A game room features striking themed decor, with large flat-screen TVs and seating. The private pool area showcases a serene swimming pool surrounded by a screen enclosure, highlighted by comfortable lounge furniture. A cozy outdoor seating area is visible, offering a relaxing view.

4.95 out of 5 average rating, 171 reviews

"Disney Serenity": Luxe 8BR Villa/ Privacy/ Pool

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, 188 reviews

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

Villa rentals with a pool

4.9 out of 5 average rating, 60 reviews

Free Arcade! All Rooms Themed! South Facing Pool!

Superhost

A screened-in pool area features a spacious swimming pool accompanied by a spa. Surrounding greenery is visible through the mesh enclosure, enhancing the outdoor experience. The deck is paved, providing ample space for lounging with chairs positioned nearby, inviting relaxation.

4.87 out of 5 average rating, 15 reviews

6BR/5BA Disney Villa, Pool+Spa, Water Views, Movie Room

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, 28 reviews

4 Suites Villa near Disney+ Hot Tub@ Magic Village

4.9 out of 5 average rating, 72 reviews

4 Miles to Disney - Pretty In Pink

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.

5 out of 5 average rating, 20 reviews

Retreat • Pool, Hot Tub & Game Lounge

4.81 out of 5 average rating, 27 reviews

Luxury Townhouse Near Disney | 3BR

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.