Villa vacation rentals in Windsor Hills

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, 206 reviews

*Plumeria Place* Minutes 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!

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4.94 out of 5 average rating, 110 reviews

The Manatee Manor | 5 BR•Windsor Hills•Game Room

Welcome To The Manatee Manor - A 5 bedroom, 5 bath home located in Windsor Hills, right in the heart of Kissimmee's tourist area, and mere minutes to the gates of Disney! With a feel of 'Better than home', you'll never want to leave. Outfitted with all the standards that you come to expect (Pool, Hot Tub, plenty of space, and serene décor), in addition to themed rooms, big screen smart TVs, and complimentary pool/hot tub heat - life doesn't get any better than when you stay at "The Manor"!

LocationFamilyParks

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.

4.94 out of 5 average rating, 146 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.

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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.

4.89 out of 5 average rating, 103 reviews

Relaxing Vacation Resort Villa

Enjoy this beautiful vacation villa in the 24-hour guard-gated Windsor Hills Resort with one of the BEST LOCATIONS IN THE RESORT, just steps away from the Resort-Style Pool & Waterpark and Poolside Cafe. RELAX and enjoy the convenience of being only 2 miles from Walt Disney World and less than 15 mins from other major theme parks. You can visit the parks in the morning, come back to have lunch at the pool, and be back in the parks for dinner and fireworks with ease. Have a Great Vacation!

ValueLocationIndoor spaces

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.

4.92 out of 5 average rating, 123 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!

FamilyLocationCleanliness

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, 268 reviews

Feel the Magic 9 min Disney, Pool & Pet Friendly

✨ Looking for comfort, privacy, and fun near Disney? Our home features a private pool and spa, perfect for relaxing after the parks. Optional pool heating is available for $49 per night. Thoughtfully prepared for families, the house welcomes guests, including those traveling with pets, for easy Florida days. Magic Kings House invites you to create unforgettable moments at Windsor Palms, a favorite resort among guests. Every detail has been carefully arranged to provide a memorable stay.

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4.86 out of 5 average rating, 138 reviews

8Bd 4K Movie Theater 155 Inch Screen Pool & Spa

A vacation home that takes your entertainment seriously! That’s our 8-bedroom villa in Emerald Island Resort at 3 miles from Disney… Ready to enjoy themed bedrooms, a premium private movie theater with a 155-inch screen, 4K projector, 5.1 surround sound, and a PS5 for gaming? Relive your favorite films in stunning quality, just like in the best movie theaters. Private Pool and Spa will make your vacation unforgettable! We’re ready for families and groups, to offer fun, comfort, and luxury.

ValueLocationParks

A private pool area is enclosed with a screened patio. The pool features a built-in spa and a spacious deck, providing ample space for relaxation. Comfortable seating options are arranged nearby, overlooking the water. The area is designed for leisure and comfort.

4.89 out of 5 average rating, 118 reviews

Luxurious Pool Villa, Minutes to Disney World

Come to enjoy our big private pool after a long day at the themes park. Sunbathing in a spacious pool deck and get a back massage by our jacuzzi. The villa had a gentle light system combined with the main cool color tone to create a feeling of comfort and relaxation. Your kids will love the Mickey twin beds and the game room area. Our villa located within 5-15minutes of majors shopping center/outlets, restaurants, bars, water parks, and themes parks. We had everything, just missing you!

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4.99 out of 5 average rating, 110 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!

FamilyValueHot tub

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.

4.95 out of 5 average rating, 166 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

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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.

4.92 out of 5 average rating, 274 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!

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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.