House vacation rentals in Windsor Hills

Disney Pool Villa | Windsor Hills | Sleeps 8

BOOK EARLY! Rated top 1% & Guest Favorite. Our popular home fills up 3-4 months in advance. 3BR/3BA Private Pool Villa in Windsor Hills Resort, Kissimmee! Newly renovated, gated resort, 3 miles to Disney World. Modern beach-coastal design, updated kitchen, family-friendly layout. Free parking, Wi-Fi, full resort access (pool, splash park, gym, playground). Near Universal (20 min), SeaWorld (18 min), Legoland (40 min). Perfect location for vacations Disney trips, sports events, and conventions.

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.

Disney Retreat | Huge Pool with Spa | 2 King beds

Don’t leave that Disney Magic at the parks - experience it by coming home to your spacious 5 BR with 2 King suites, 3.5 baths, and newly renovated design. The high ceilings and open floor plan make it perfect for family time, while the private backyard oasis, complete with a pool and spa (heating optional) and Tiki Bar, offers a great space for relaxation. The themed bedrooms, including Star Wars, Frozen, and Mickey & Minnie, add a fun and whimsical touch that’s perfect for guests of all ages.

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

★Completely Renovated★ 3 mi to Disney+Free Resort!

Closest FREE resort to Disney Parks! Sandpiper Shores is a 6 bedroom 4 bathroom luxury villa that sleeps 14. BEST STAR RATING - OVER 200 REVIEWS! * Kitchen is loaded & all baby gear provided. * Custom game room with A/C, LED panel lighting, & ROCK CLIMBING WALL! * Roku smart TVs & NEST tech throughout. * Outdoor space includes your own private pool, hot tub, overhead lighting, NEW grill, & 10' custom-built farmhouse table to seat the whole family! Every detail has been thought of!

Themed Windsor Hills 6BR Private Pool Gameroom

Welcome to Happy Thoughts Villa Enjoy this luxurious 6-bedroom, 4-bathroom home in Windsor Hills Resort, just 3 miles from Disney! Features include a private heated pool/spa, game room, updated kitchen, 2 king suites, a queen room on the main level, and 3 themed kids’ rooms (Frozen, Minions, Mandalorian). Resort amenities include a water park, arcade, gym, playgrounds, and more—all within an 8-minute walk. Located in a 24-hour gated community, it’s the perfect spot for your dream vacation!

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.

Luxury 5BR, Pool, Theater & Game Room, Near Parks

Welcome to Gracey Manor, a luxurious vacation villa just minutes from Disney’s Doorstep. The home sleeps 12 and features a private pool, spa (heat included), home theater and game room. Queen bedroom on the main floor with a full bath. Master King Bedroom with full en suite, second King bedroom with private bath, 2 Twin bedroom, Double Bunk Bedroom and full bathroom. Netflix and Disney+ also included.

Ultimate Family Escape • 6BR Luxury Villa • Minute

Ultimate 6BR Disney getaway just minutes from the parks! FREE pool heat & BBQ, ultra-soft signature blankets, and full resort access with water slides, pool, gym & more. Private, spotless home with easy keyless entry and direct owner support. Designed for families who want comfort, convenience, and a truly memorable stay.

Popular 6BR Resort Home 4 mi Disney/Pool/Game Room

Welcome to your magical family villa located in Windsor Hills Resort. This 6-bedroom, 4-bathroom home is designed to provide you with luxurious comfort and non-stop entertainment, making your Disney-area vacation truly exceptional. ⭑CONTACT US FOR SEASONAL DISCOUNTS⭑

2584 - 6 Bedroom w/ Pool and Water Park Included

This charming 6-bedroom vacation home in Windsor Hills Resort is perfect for the entire family. Located in one of the finest gated communities in the area, the resort features 24-hour security, ensuring that only registered guests have access to the neighborhood.