Vacation rentals in Windsor Hills

*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!

Free Waterpark|Game Room|Near Dis!

Welcome to Playcation Paradise by Cosmic Vacations. This is your dream getaway in Windsor Hills Resort—just 3 miles from Disney World, 15 miles from Universal, and only 0.4 miles to Windsor Hills’ incredible amenities! Enjoy your private pool and spa, or have a blast in the custom game room with commercial-grade arcade games set to free play. Plus, you’ll have free access to Windsor Hills’ top-tier amenities, including a lagoon-style pool, water slides, and sports courts.

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.

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.

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!

Arcade + Pool Villa • 2.5 Miles to Disney

📍 Windsor Hills Resort • 0.3 miles to clubhouse 🎮 Mario themed arcade 👑 Princess room + slide 🚀 Toy Story room + slide 👗 Dress-up corner 🟢 Toy Story ball pit 🏊 Private pool 🌊 Resort pool + slides 💪 Gym + Pickleball 🎾 Tennis + Basketball 📍 ~2.5 miles to Disney 👶 Stroller + pack ’n play 🚗 No resort fees 🔥 Pool heat available (fee) 🚧 Gated resort 🚗 Free parking.

Themed Rooms • Private Pool • Family Dream Stay

Step into a fully themed, design-forward escape just minutes from Walt Disney World®, where every room tells a story and every detail is curated for unforgettable stays. Whether you're here for family fun or a magical getaway, this home blends comfort, style, and experience in one place. Unwind in your private pool and spa overlooking the tranquil Windsor Hills lake—where sunset swims and quiet mornings become part of the memory.

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!

Windsor Hills | Pool | 2.5mi to Disney | Themed

Welcome to Belle’s Villa — your family’s ideal home base just minutes from Disney. Skip the cramped hotel room and enjoy your own private pool, thoughtfully designed spaces, and a home where both kids and parents can truly relax. Located in the highly sought-after Windsor Hills Resort, you’ll be close to the parks while enjoying a quiet, comfortable retreat at the end of each day.