Holiday rentals in Windsor Hills

:NEW: CasaD'Disney Spacious Villa- Next 2 DiSNeY

You hit the JACKPOT and found my newest listing! Calendar is wide open, but filling up fast! Don't DELAY! • *UPDATE*: Fully REMODELED & Painted now in July 2023!!!! • Meticulously CLEAN & Spacious Disney home in the #1 community in the Disney Area, Windsor Hills • Just MINUTES from DISNEY Maingate!!! • *HIGHLY Rated Host----Please READ my reviews---- 345 '5-Star Reviews can't be wrong!' • 2 Master Suites! • 2 children themed bedrooms (Princess & Star Wars) • Onsite, driveway parking for 3 vehicl

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.

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!

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!

*Brand New*! Minutes to Disney! + Free Resort!

Closest FREE resort to Disney Parks! We've named it "Coral Cove" - a 6 bedroom 4 bathroom luxury villa that sleeps 14. Completely renovated in Dec 22! * Kitchen is loaded, & all baby gear provided. * Custom game room with A/C, LED panel lighting & ROCK CLIMBING WALL! *Outdoor space includes your own private pool, hot tub, overhead lighting, NEW BBQ grill & 10' custom-built farmhouse table to seat the whole family! *New Roku smart TVs & NEST tech! *Every detail has been thought of!

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!

Luxurious home 2 miles from Disney - Windsor Hills

The Bella Vita Villa has just been recently remodeled and is ready for you to book! This private villa offers new updated furniture, flooring and paint (inside out). After a long day from the theme parks, shopping, or adventuring the local Orlando area there is beautiful pool oasis to relax in. You just found your dream vacation home in Kissimmee, close to Disney. Located in the high-end gated subdivision of Windsor Hills, the closest five star community to Disney (only 2 miles)!

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

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.

Fun, Sun, Theme Parks and More

Build lasting vacation memories and sleep in style just minutes from Disney World. Your family will be at home in this spacious 3 bedroom townhouse with its own private heated pool (no extra charge) and full kitchen. And when you're not at Disney, it's just a 5 minute walk to the clubhouse and FREE heated pool and water park at the fabulous Windsor Hills resort.

Windsor Hills Home w/Arcade Game Room|Near Disney

Windsor Hills Resort with water park, heated pool, and sports courts. Only 10 minutes to Disney. Renovated home with private pool, BBQ grill, and no rear neighbors. Features Harry Potter and Princess-themed bedrooms and a game room with arcade games. Perfect for families and groups.

10 BD/ 10.5 BA Sleeps 20! Encore At Reunion(205SS)

• Resort: Encore At Reunion • THERE IS NO ACCESS TO RESORT AMENITIES • 10 Bedrooms/ 10.5 Bathrooms/ Sleeps 20 • Disney (5.1 mi) SeaWorld (16.4 mi) Legoland (30.0 mi) • Convention Center (8.5 mi) Universal Studios (18.6 mi) • Location: Southfield Street, Kissimmee FL 34747