Holiday rentals in Windsor Hills

A spacious living area is seen, featuring a large sectional sofa adorned with decorative pillows. Natural light enters through expansive glass doors, providing a view of the backyard and pool area. Elegant light fixtures hang from the ceiling, complementing the neutral color palette.

5 out of 5 average rating, 117 reviews

Cinderella's HolidayVilla-Minutes from Disney-NEW!

• 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 FULLY REMODELED in Sept 2022!

An outdoor dining area features a large, custom-built wooden table surrounded by black chairs. Blue plates and glassware are meticulously arranged for an inviting meal. A bright blue pool glimmers in the background, enclosed by a mesh screen to ensure privacy.

4.96 out of 5 average rating, 169 reviews

*Hibiscus Hideaway* 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!

A private pool area is enclosed with a screen, revealing a sparkling pool surrounded by lounge chairs. The living room features comfortable seating arranged around a coffee table, complemented by large windows. An entertainment area showcases arcade games and a race car setup, while a hot tub offers a spot for relaxation.

4.92 out of 5 average rating, 79 reviews

Windsor Hills 5BR • Free Heat • Private Arcade

Just 2 miles to Disney! 5BR/5BA Windsor Hills villa sleeps 12 with PRIVATE free-play arcade, FREE heated pool & spa, and BBQ grill. Kids love the Harry Potter & Star Wars themed rooms! Located in gated Windsor Hills Resort with 24/7 security. Fast 500Mbps WiFi, 65" smart TVs. Pets welcome ($350/stay). EV charger available ($20/night). Book your dream Disney vacation today! Pack light! Stroller, pack-n-play & high chair available for your stay. Arcade set to free play — no quarters needed!

5 out of 5 average rating, 17 reviews

Themed Villa:10 min to Disney: Pool, Gameroom, BBQ

Welcome to Colorful Haven, a vibrant family getaway near Disney and other top attractions. Enjoy an exceptional experience as you splash in a private pool, play fun games, enjoy outdoor dining, and relax in rooms with an amazing theme. Plus, enjoy access to resort amenities including the waterpark, sports courts, fitness center, and clubhouse. Disney World - 8 min drive Old Town - 14 min drive Universal Studios - 30 min drive Book For Unforgettable Memories In Kissimmee—See Details Below!

4.99 out of 5 average rating, 108 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!

A vibrant games room is equipped with various arcade machines, including SpongeBob Racing. A massage chair is positioned nearby, while a theater room features plush seating. An outdoor space highlights a screened-in pool area surrounded by palm trees, visible through large windows.

4.99 out of 5 average rating, 254 reviews

Windsor Orlando Private Arcades,Theater,Pool-Spa

Orlando, Disney, Arcade, Movie Theater, Massage Chair, Pool, Hot Tub, 2 King Beds, Kids Bunk Bed, Kissimmee. Upgraded games room IN the private home, theater for evenings home and your private lanai with pool and hot tub. Choose from including Pump It Up dance, Sponge Bob Racing, NASCAR racing, Legends 3, Pac-Man's Arcade Party, an 80-inch TV, and an Xbox 360. Watch your favorite movies on the 92-Inch projection screen, surround sound, and stadium style seating.

Superhost

4.73 out of 5 average rating, 70 reviews

Villa | Game Room & Summer Kitchen | 8 min Disney

Welcome to your dream Orlando getaway! Perfectly located just minutes from Disney, this beautiful 6-bedroom home is designed for families and groups seeking both comfort and fun. Enjoy a private pool with spa and summer kitchen, spacious living areas, and a fully equipped kitchen for family meals. Everyone will love can gather in the game room for entertainment. The clubhouse with resort-style amenities is just a short walk away for even more vacation fun.

Superhost

A spacious living area features a contemporary design with a large flat-screen TV mounted on the wall, surrounded by comfortable seating. A stylish coffee table is centered on a soft area rug, and decorative plants add a touch of greenery. The bright space is complemented by warm lighting.

4.9 out of 5 average rating, 30 reviews

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!

4.98 out of 5 average rating, 57 reviews

Once upon a galaxy: Star Wars/fairytale retreat

Welcome to Windsor Dreams, a stunning and family friendly 6 bedroom, 4 bathroom home in the incredible Windsor Hills resort, the CLOSEST private resort with single family homes to Disney World. You'll have a private movie theater IN the home, private pool/spa, theme rooms, and a world of comfort close to Disney.