
Vacation rentals in Windsor Hills
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Top-rated vacation rentals in Windsor Hills
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Magical Adv 5 Star Villa Movie Room Arcade Pool an
Experience enchantment at Magical Adventure Villa, a top-rated 6-bedroom and 4-bath home for 12 guests. Conveniently located in Windsor Hills Resort, just 2 miles from Disney World®. Experience the highly acclaimed getaway that has garnered rave reviews. Enjoy a private pool, home theater, and a thrilling arcade. Unleash your inner Jedi at the state-of-the-art Star Wars gaming center with a movie theater, Xbox One, Nintendo Switch, and immersive 3D designs. *Work vehicles are not permitted to b

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.

Magical 6BR Family Retreat w/ Pool Near Disney
✨ Poke’s Dreamy Disney Getaway ✨ 🏡 House Features: ❄️ Frozen-Themed Bedroom for a magical escape 🎸 Coco-Themed Bedroom full of vibrant charm 🎮 Mario Mansion Game Room with exciting arcade vibes 💦 Private Patio with Heated Pool 🍳 Entertainer’s Kitchen for unforgettable family meals 📶 Fiber High-Speed Wi-Fi 🛏️ Sleeps up to 13 Guests 🎢 Resort Amenities: 🏞️ Clubhouse with Water Slides, Hot Tub, and Pool 🎥 Movie Theatre and Arcade 🏸 Sports Facilities: Tennis, Basketball, Pickleball, and

*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!

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!

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.

Luxury Villa Windsor Hills Resort 2 miles / Disney
4 bed and 4 bath LUXURY VILLA located in the top rated WINDSOR HILLS RESORT, just 2 MILES / 5 MINUTES AWAY from Walt Disney World This Villa is newly renovated, immaculately clean, and has all you need for a fun and comfortable vacation. The Villa offers the ultimate game room, outdoor dinning, and a screened private pool & spa. All guests also have access to resort amenities. Lots of entertainment for all. * Security Deposit Required with reservation

Windsor Hills Single Level 4BR Home, Pool, GameRm
Welcome to this beautiful 4-bed, 4-bath Windsor Hills villa, just a few miles from Disney World! Perfect for families, this modern, spacious vacation home offers comfort, style, and access to resort amenities with no parking or resort fees. Relax, recharge, and create unforgettable memories in this family-friendly Orlando vacation rental, combining convenience, charm, and fun for an unforgettable Disney getaway.

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.

*EPIC Bunk Slide*Minutes to Disney*FREE Pool Heat*
In a Galaxy far far away… You and your band of rebels will journey to a small rebel outpost, in the coveted Windsor Hills Resort, to find your way with the force. Located just 5 miles from Walt Disney World Resort and 20 minutes from Universal Orlando and SeaWorld! Follow us on Insta @galactic_escape_kissimmee
Popular amenities for Windsor Hills, Four Corners vacation rentals
Stay near Windsor Hills's top sights
Windsor Hills, Four Corners home rentals

Paradise Cove at Windsor Hills Resorts

Disney Pool Villa | Windsor Hills | Sleeps 8

*NEW*Theater, FREE Resort, 3 Kings, 2 mi WDW

Disney Vacation Home w/ Pool, Hot Tub + GameRoom

FREE Heated Pool! 5BR Disney Villa, Themes+Games

Family Disney Home | Pool | Game Room | Hot Tub

*Magical Getaway* w/ Heated Pool! Close to Disney

Dream Stay: Resort Pool Villa minutes to Disney
Windsor Hills, Four Corners condo rentals

Minutes to Disney best of Home, with a Resort feel

Magical Stay Near Disney & ESPN

Disney's Doorstep, 3 Bed 2 Bath, Waterslides!

Beautiful 2/2 Gem, 2 mi to Disney with Water Park!

Lovely vacation condo close to Disney & Universal!

Westgate Vacation Villas - 1 Bedroom

3Br Poolside Windsor Hills, Waterpark, Disney 2mi

WH Condo. Pool/Waterpark and close to Disney!
Other great vacation rentals in Windsor Hills

Windsor Hills 5BR • Free Heat • Private Arcade

Bluey Fun| Free Water Park | 8 min to Disney

3 Miles 2 Disney | DisneyThemed | Fully Renovated

Themed Family Pool Home 10 Min to Disney Game Room

Dreaming Home -FREE Water Park at Windsor Hills

Magical Stays Near Disney

The Manatee Manor | 5 BR•Windsor Hills•Game Room

Exquisite Escape At Windsor Hills
When is the best time to visit Windsor Hills?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ834 | ﺩ.ﺇ852 | ﺩ.ﺇ914 | ﺩ.ﺇ918 | ﺩ.ﺇ823 | ﺩ.ﺇ848 | ﺩ.ﺇ900 | ﺩ.ﺇ823 | ﺩ.ﺇ746 | ﺩ.ﺇ812 | ﺩ.ﺇ892 | ﺩ.ﺇ1,021 |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
Quick stats about vacation rentals in Windsor Hills

Total vacation rentals
Explore 640 vacation rentals in Windsor Hills

Nightly prices starting at
Windsor Hills vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees

Verified guest reviews
Over 13,540 verified reviews to help you choose

Family-friendly vacation rentals
590 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Vacation rentals with a pool
630 properties feature pools

Rentals with dedicated workspaces
380 properties have a dedicated workspace

Wi-Fi availability
640 of Windsor Hills vacation rentals include wi-fi access

Popular amenities for guests
Guests love Self check-in, Gym, and BBQ grill across Windsor Hills rentals

4.7 Average rating
Windsor Hills stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Rentals with a hot tub Windsor Hills
- House rentals Windsor Hills
- Rentals with a patio Windsor Hills
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- Rentals with pools Windsor Hills
- Family-friendly rentals Windsor Hills
- Condo rentals Windsor Hills
- Rentals with an EV charger Windsor Hills
- Pet-friendly rentals Windsor Hills
- Rentals with outdoor seating Windsor Hills
- Rentals with a home theater Windsor Hills
- Serviced apartment rentals Windsor Hills
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort
- Walt Disney World Resort Golf
- Disney Springs
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- ESPN Wide World of Sports
- Give Kids the World Village
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Aquatica
- Camping World Stadium
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
- Reunion Resort Golf Courses - Palmer & Watson




