
Holiday rentals in Windsor Hills
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Windsor Hills
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

*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!

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!

Dream Stay: Resort Pool Villa minutes to Disney
Welcome to this recently renovated 6B/4B pool/hot tub villa in the coveted Windsor Hills Resort: ○ 3 miles from Disney Parks ○ X-Men themed game room with Wii console and arcades ○ Private pool and spa ○ Short walk to clubhouse with pool & slides ○ High speed Wi-Fi ○ Themed kid's rooms including Disney princess and dragons ○ Top rated gated resort community *Windsor Hills* with amenities including water park, waterslide, arcade room, movie room, gym, playground, tennis courts & more

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)!

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.

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

Family Disney Home | Pool | Game Room | Hot Tub
This 4-bed home in Windsor Hills is the ultimate Disney retreat. Just 3 miles from the parks, it offers a private pool and total privacy with no rear neighbors. - Space: Sleeps 8 in 4 bedrooms, each with a private bathroom and TV. - Pool & Spa: Screened-in heated pool and hot tub with a fenced yard. - Family Fun: Game room with pool/air hockey plus resort water park access. - Convenience: Full kitchen, laundry, and parking. Minutes from Disney, dining, and shopping.

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!
Popular amenities for Windsor Hills holiday rentals
Stay near Windsor Hills's top sights
Other great holiday rentals in Windsor Hills

Windsor Hills | Heated Pool | Disney | Sleeps 6-8

Windsor Hills 5BR • Free Heat • Private Arcade

10 min to Disney| Themed | Sauna | Pool | Golf Sim

Dazzling 5 bedroom Windsor Hills Home 7781

4BR/4BA Premium Themed Villa

Premium 4BR Home near Disney | Windsor Hills

Poolside TV, 3 Kings, FREE Waterpark, AC Game Rm

3 miles to Disney! Cozy Home Heated Pool Spa & PS5
When is the best time to visit Windsor Hills?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $291 SGD | $297 SGD | $319 SGD | $321 SGD | $287 SGD | $296 SGD | $314 SGD | $287 SGD | $260 SGD | $283 SGD | $312 SGD | $356 SGD |
| 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 holiday rentals in Windsor Hills

Total holiday rentals
Explore 640 holiday rentals in Windsor Hills

Nightly prices starting at
Windsor Hills holiday rentals start at $64 SGD per night before taxes and fees

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

Family-friendly holiday rentals
590 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Holiday rentals with a pool
630 properties feature pools

Rentals with dedicated workspaces
380 properties have a dedicated workspace

Wifi availability
640 of Windsor Hills holiday rentals include wifi 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
- House rentals Windsor Hills
- Family-friendly rentals Windsor Hills
- Rentals with a patio Windsor Hills
- Villa rentals Windsor Hills
- Rentals with pools Windsor Hills
- Fitness-friendly rentals Windsor Hills
- Rentals with a washing machine and dryer Windsor Hills
- Rentals with a hot tub Windsor Hills
- Rentals with a cinema Windsor Hills
- Pet-friendly rentals Windsor Hills
- Rentals with outdoor seating Windsor Hills
- Serviced apartment rentals Windsor Hills
- Flat rentals Windsor Hills
- Apartment rentals Windsor Hills
- Rentals with an EV charger Windsor Hills
- Walt Disney World Resort
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Disney Springs
- SeaWorld Orlando
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- ESPN Wide World of Sports
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Give Kids the World Village
- Camping World Stadium
- Aquatica
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- ChampionsGate Golf Club




