Holiday rentals in Windsor Hills

Game & Theater Room, Castle Bunks, Pool & Spa

Vacation at Windsor’s Best located in Windsor Hills Resort just 2 miles from Walt Disney World. This one-story 4 bed, 4 bath vacation villa has everything you need for a wonderful getaway with family or friends. Situated on an elevated corner lot, this spacious villa with it's private pool and spillover spa offers a beautiful view overlooking the resort community. Plus, guests have access to the family-friendly Windsor Hills Resort amenities, including the water park, playgrounds, gym and more.

*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!

Resort Home 3.5 miles to Disney with home theater

We welcome you to stay in our home located in the Windsor Hills community with a water park, slides, theatre and so much more! The house is just 3.5 miles from Disney’s Animal Kingdom. Our home has 6 large bedrooms including laundry in the home, an 8 seat home theatre, TVs in every room, a large swimming pool & spa with a large patio cover, plus a large kitchen fully equipped with everything you need for your stay. Please message us if you have any questions, we look forward to hosting you!

Highest Rated Minutes to Disney! -Newly Renovated

• Newest house in the #1 community in the Disney Area, Windsor Hills • Only home with 7 bedrooms in the community (3 KING beds) • Extra privacy: only one side & no rear neighbors • 4 children themed bedrooms (Mickey, Star Wars, Toy Story, & Frozen) • Onsite, driveway parking for 4 vehicles • FREE pool heat + BBQ with all rentals • Fully equipped + stocked kitchen • Self check-in with digital lock • Super FAST Wi-Fi wireless internet speed at +1000 Mbps • Property is managed directly by owner

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!

Windsor Hills Resort 5 Bedroom Home with Game Room

Stay at "Marvelous Dream" a Windsor Hills Resort Vacation Home - Includes Resort Clubhouse Amenity Access! Our 5-bedroom, 5-bathroom private vacation home is perfect for families seeking the ultimate home base to experience the very best of Central Florida. Designed with an unparalleled guest experience in mind, our home offers a perfect blend of comfort and fun, featuring a private pool, a relaxing spa, and a game room for your family's enjoyment.

Single-Level Pool Home, Resort Amenities, Disney

Welcome to this single-level fun house by FunStay Homes featuring unique themed rooms and a private pool/spa. - 24/7 gated community - Amazing Windsor Hills Resort amenities - No rear neighbors with open green space - Themed rooms: Harry Potter, Star Wars, Spiderman, Minions - 2 King Beds and 4 twin beds - Free Wifi and TV in every room - Pool/Spa heat available for an additional fee - Complimentary offerings include no resort fees

Stunning 4BR Villa in Windsor Hills / Near Disney

Beautiful 4BR/4BA Single-Story Home in Windsor Hills | Toy Story Room | Near Disney Welcome to your perfect Disney vacation home! This one-story, 4-bedroom, 4-bathroom retreat is located inside the highly desirable Windsor Hills Resort, just 2 miles from Walt Disney World. With a smart layout, private bathrooms for every bedroom, and a fun Toy Story–themed kids room, this home is ideal for families and groups looking for comfort and convenience.

Parkside Windsor Retreat 15 Min Disney!

Fully Renovated in for 2026. This Immaculate Getaway Is Ready For Your Perfect Orlando Vacation. Minutes to Disney, Universal and Sea World. 50 min to Legoland. 3 Bedroom 3 Bath Townhome Featuring Private Pool and Patio. Located In Beautiful Windsor Hills Resort. Featuring Water Slide and Splash Park!! Amazing Amenities and CLOSE TO EVERYTHING!! Walking Distance to Clubhouse Pool. Private GATED Community. This Location HAS IT All.

Hibiscus Villa w/ themed rooms, game room and pool

Welcome to your luxurious single story 4-bedroom getaway in the heart of a gated resort just 2.6 miles from the magic of Disney World! This meticulously designed vacation home offers not only comfort and convenience but also an array of resort amenities that promise an unforgettable stay. Your dream vacation home is not just a place to stay; it's a gateway to a world of enchantment and relaxation. Book your stay now and let the magic begin!

Modern Resort stay +Private Pool

Sleek, modern townhome in Windsor Hills Resort—just 2 miles from Disney! 3 bedrooms (fun kids' bunk room + luxe master), private plunge pool, and 5★ resort perks: water park, pool, spa, bar, kids club, mini golf, and more. Walkable, gated, family-friendly. Steps from Walmart & dining. Your dream Florida stay—without the all-inclusive price tag! Your vacation should feel effortless—and this townhome delivers just that!

3 miles to Disney! Comfy Villa w/Pool Spa GameRoom

3 Miles to Disney | Free Pool & Spa Heat | Windsor Hills Resort | Star Wars Game Room | Themed Rooms | Tastefully Decorated Escape the chaos and make unforgettable memories at Central Breeze Villa—a stylish, fun-filled 6BR/4BA private pool home in the highly sought-after Windsor Hills Resort, just 3 miles from Disney World!