
Holiday rentals with a hot tub in Windsor Hills
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Top-rated rentals with a hot tub in Windsor Hills
Guests agree: these rentals with a hot tub are highly rated for location, cleanliness and more.

: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.

★Completely New★ 3 miles to Disney + Free Resort!
Closest FREE resort to Disney Parks! Plumeria Place is a 6 bedroom 4 bathroom luxury villa that sleeps 14. Completely renovated in March 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 & 9' 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!

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.

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

StarWars Theme + Free Waterpark | 10 min to Disney
Family-friendly Star Wars Retreat in Windsor Hills Resort — just 10 minutes from Walt Disney World! Enjoy a private screened splash pool, smart TVs in every room, fully equipped kitchen with fun themed touches, and FREE access to resort waterpark, lagoon pool, hot tub, arcade, playgrounds, and sports courts. Washer/Dryer in the home. Spacious, modern, and perfect for multigenerational stays or longer vacations.

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.

Mickey Pool • Frozen • Waterpark • Near Disney
✨ Experience the magic as you step into our 3-bedroom townhome at Windsor Hills, one of the closest resorts to the Disney Parks. Relax in your private, heated Mickey-themed pool, explore a Frozen-inspired bedroom, and enjoy full access to the resort’s pools, water park, movie theater, and more. It’s the perfect home base for making Disney memories together. ✨
Popular amenities for rentals with a hot tub in Windsor Hills
House rentals with a hot tub

Paradise Cove at Windsor Hills Resorts

6BR Themed Villa | Theater | Pool & Spa with View

5Bd/4Ba Game Rm Pool Spa Theater Close 2 Theme Pk

Disney Pool Villa | Windsor Hills | Sleeps 8

Once upon a galaxy: Star Wars/fairytale retreat

Fantastic home just 3 miles from Disney World!

Elegant Disney Themes | Pool, Hot Tub & Game Room

Disney Escape at Windsor Hills
Villa rentals with a hot tub

4mi to Disney | Games | Private Pool

Luxurious Pool Villa, Minutes From Disney World

Cheerful Villa (7br / 6.5ba) Minutes to Disney

*Private Resort Oasis: Golf-Front, Pool/Spa/Cinema

Tinkerbells Castle 2 Pool & Spa, Disney Fire Works

Luxury Villa! /Game Room/ Pool Heater

Disney Dream Villa- 10 Minutes From Disney!

8Bd 4K Movie Theater 155 Inch Screen Pool & Spa
Cabin rentals with a hot tub

Authentic Disney Fort Wilderness Cabin near WDW-1

The porch

Sunny Margaritaville Cottage - Private Pool, Full

Mouse House Cabin/ Legacy Disney Fort Wilderness

Authentic Disney Fort Wilderness Cabin near WDW-2

The Potter’s Cottage

Happy Margaritaville Cottage w Amenity Access
When is the best time to visit Windsor Hills?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $298 SGD | $299 SGD | $325 SGD | $339 SGD | $289 SGD | $303 SGD | $329 SGD | $295 SGD | $265 SGD | $294 SGD | $322 SGD | $376 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 with a hot tub in Windsor Hills

Total holiday rentals
Explore 430 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 9,950 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Holiday rentals with a pool
430 properties feature pools

Rentals with dedicated workspaces
250 properties have a dedicated workspace

Wifi availability
430 of Windsor Hills holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Windsor Hills rentals

4.8 Average rating
Windsor Hills stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
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- Rentals with a hot tub Four Corners
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- Rentals with a hot tub United States
- 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




