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Villa vacation rentals in Windsor Hills

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Top-rated villa rentals in Windsor Hills

Guests agree: these villas are highly rated for location, cleanliness, and more.

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Guest favorite
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.
Villa in Kissimmee
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

Guest favorite
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.
Villa in Kissimmee
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!

Top guest favorite
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.
Villa in Kissimmee
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!

Top guest favorite
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.
Villa in Kissimmee
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.

Top guest favorite
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
4.99 out of 5 average rating, 137 reviews

*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.

Guest favorite
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.
Villa in Kissimmee
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.

Top guest favorite
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.
Villa in Championsgate Village
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!

Top guest favorite
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.
Villa in Davenport
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!

Top guest favorite
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.
Villa in Kissimmee
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!

Top guest favorite
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.
Villa in Kissimmee
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

Top guest favorite
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.
Villa in Kissimmee
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!

Guest favorite
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.
Villa in Kissimmee
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

When is the best time to visit Windsor Hills?

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Avg. priceﺩ.ﺇ856ﺩ.ﺇ837ﺩ.ﺇ929ﺩ.ﺇ973ﺩ.ﺇ852ﺩ.ﺇ848ﺩ.ﺇ936ﺩ.ﺇ834ﺩ.ﺇ735ﺩ.ﺇ823ﺩ.ﺇ903ﺩ.ﺇ1,054
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Quick stats about villa rentals in Windsor Hills

  • Total vacation rentals

    Explore 150 vacation rentals in Windsor Hills

  • Nightly prices starting at

    Windsor Hills vacation rentals start at ﺩ.ﺇ404 per night before taxes and fees

  • Verified guest reviews

    Over 3,110 verified reviews to help you choose

  • Family-friendly vacation rentals

    140 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Vacation rentals with a pool

    140 properties feature pools

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    150 of Windsor Hills vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Windsor Hills rentals

  • 4.8 Average rating

    Windsor Hills stays are highly rated by guests—averaging 4.8 out of 5!

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