Windsor Hills holiday rentals
We found 2,639 holiday rentals — enter your dates for availability
Select from 169 houses, 64 flats and other holiday rentals to find the perfect place for your stay in Windsor Hills. Whether you’re travelling with friends, family or just with your pet, holiday rentals have the amenities that you expect for your stay, such as air conditioning and Wi-Fi. You'll be able to choose a property to rent for everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts – Windsor Hills
Showing deals for:8 Jan - 15 Jan
Exceptional
(61 reviews)
Welcome to The Windsor Wonder!
Kissimmee
S$3,365
for 7 nights, 1 villa
S$481 per night
includes taxes & fees
Exceptional
(167 reviews)
Welcome to The Windsor Fantasy with Brand New Professional Arcade Room!
Kissimmee
S$3,113
for 7 nights, 1 villa
S$445 per night
includes taxes & fees
Exceptional
(197 reviews)
Magical Vacation Home with Kid-Themed Rooms 3 Miles from Disney
Kissimmee
S$2,773
for 7 nights, 1 home
S$396 per night
includes taxes & fees
Exceptional
(12 reviews)
EPIC! Themed-Arcade-Theatre-Pool Table-Pool&Spa-3mi>Disney
Kissimmee
S$3,818
for 7 nights, 1 home
S$545 per night
includes taxes & fees
Exceptional
(6 reviews)
Mickey’s Vacation Villa-Premium- Minutes from Disney World with private pool!
Kissimmee
S$5,360
for 7 nights, 1 home
S$766 per night
includes taxes & fees
Exceptional
(107 reviews)
6BR Family Retreat Near Disney | Pool + Arcade + Resort Access
Kissimmee
S$3,386
for 7 nights, 1 home
S$484 per night
includes taxes & fees
Exceptional
(34 reviews)
Fully Renovated w Heated pool, 3 miles from Disney
Kissimmee
S$5,658
for 7 nights, 1 home
S$808 per night
includes taxes & fees
Exceptional
(26 reviews)
Welcome to The Windsor Treasure with Professional Arcade Room! Brand New 2024!
Kissimmee
S$3,436
for 7 nights, 1 villa
S$491 per night
includes taxes & fees
Wonderful
(61 reviews)
Windsor Hills - Right at Disney's Doorstep. Universal Studios, SeaWorld.
Kissimmee
S$1,478
for 7 nights, 1 apartment
S$211 per night
includes taxes & fees
Exceptional
(16 reviews)
Theme Parks, Heated Pool, Theater, Arcades, Mario Kart Bedroom
Kissimmee
S$3,698
for 7 nights, 1 home
S$528 per night
includes taxes & fees
Exceptional
(19 reviews)
Luxary villa close to disney
Kissimmee
S$1,895
for 7 nights, 1 villa
S$271 per night
includes taxes & fees
Exceptional
(97 reviews)
Harry Potter Villa - 10 Mins to Disney
Kissimmee
S$3,271
for 7 nights, 1 villa
S$467 per night
includes taxes & fees
Exceptional
(36 reviews)
Paradise Villa, No rear neighbors, Minutes from Disney
Kissimmee
S$2,546
for 7 nights, 1 home
S$364 per night
includes taxes & fees
Exceptional
(151 reviews)
Getaway with Mickey in Windsor Hills!
Kissimmee
S$1,576
for 7 nights, 1 apartment
S$225 per night
includes taxes & fees
Exceptional
(124 reviews)
Star Wars Villa - 10 Mins to Disney
Kissimmee
S$2,903
for 7 nights, 1 villa
S$415 per night
includes taxes & fees
Exceptional
(133 reviews)
Amazing Private Theater and Game Room! Pool/Spa & Star Wars room! Free Pool Heat
Kissimmee
S$3,092
for 7 nights, 1 home
S$442 per night
includes taxes & fees
Exceptional
(138 reviews)
Cinderella Pool Villa - 10 minutes from Disney
Kissimmee
S$2,744
for 7 nights, 1 villa
S$392 per night
includes taxes & fees
Exceptional
(218 reviews)
3 BR Condo with Beautiful Pool & Water Park Minutes to Disney Worlds Front Gate
Kissimmee
S$1,806
for 7 nights, 1 apartment
S$258 per night
includes taxes & fees
Exceptional
(5 reviews)
New listing - Free Wifi - private pool - 3 miles to Disney
Kissimmee
S$1,689
for 7 nights, 1 home
S$241 per night
includes taxes & fees
Exceptional
(92 reviews)
😎RELAX at Windsor Hills🌴, minutes to Disney - 5 bed / 5 bath, Private Pool🌞
Kissimmee
S$2,602
for 7 nights, 1 home
S$372 per night
includes taxes & fees
Exceptional
(256 reviews)
Family friendly, 10 mins to Disney, WIFI, Resort style amenities, Backyard pool
Kissimmee
S$1,808
for 7 nights, 1 home
S$258 per night
includes taxes & fees
Wonderful
(235 reviews)
Vacation Rental near Disney, Univeral Studios, Epic, w/free parking and Wi-Fi.
Kissimmee
S$1,658
for 7 nights, 1 apartment
S$237 per night
includes taxes & fees
Exceptional
(106 reviews)
Monorail Silver | Near Disney & ESPN | Private Pool | No Rear Neighbors
Kissimmee
S$2,140
for 7 nights, 1 home
S$306 per night
includes taxes & fees
Exceptional
(134 reviews)
Renovations Kitchen & Bath. "Be Our Guest" in Windsor Hills-pool heat included
Kissimmee
S$2,361
for 7 nights, 1 home
S$337 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Windsor Hills
1 Sunny Pool Paradise, Disney Magic, Golf, Animal Kingdom, Universal Studios!
Sleeps 6 · 3 bedrooms · 3 bathrooms
Fabulous Lake View/South Facing Pool Home- Game room -2 Miles to Disney!
Sleeps 10 · 5 bedrooms · 5 bathrooms
🌴Beautiful home in Windsor Hills Resort -Disney 2.5 miles 🌴
Sleeps 7 · 3 bedrooms · 3 bathrooms
2Pool Home Water Park Disney 2 m Universal Sea World! By Mystic Dunes golf !
Sleeps 6 · 3 bedrooms · 3 bathrooms
Welcome To Magnolia Blossom Villa! South Facing Pool in Prime Location.
Sleeps 14 · 6 bedrooms · 4 bathrooms
Windsor Hills Town Home! So Close You Can Feel the Magic!
Sleeps 8 · 3 bedrooms · 3 bathrooms
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
How much does it cost to rent a holiday rental in Windsor Hills?
Season, property type and length of stay are some of the things that can affect the price of a holiday home. Simply add your travel dates to find your perfect escape. From homey country cottages to expansive villas, all Vrbo holiday rentals offer terrific value.
How much does it cost to rent a beach house in Windsor Hills?
When you travel and the style and size of the property will help determine the cost of your beachside holiday rental. Put in your Windsor Hills travel dates to see your options on Vrbo. Can't live without a private pool? Use our filters to select the amenities and features you want in your beach house.
What are the top attractions for families in Windsor Hills?
Keep your kids occupied at these fabulous family-friendly attractions in Windsor Hills:
- Surfari Water Park
- Northeast Regional Park
- Lake Davenport
How old do you have to be to rent a holiday rental in Windsor Hills?
The minimum age requirements can differ across properties on Vrbo, so check the rules of the holiday home in Windsor Hills you want to book. But typically, it's 16, 18 or 21.
How long can I rent a holiday rental in Windsor Hills for?
The amount of time you can stay in a Windsor Hills holiday rental for is down to the property. Just tap in your dates of travel to view options offering longer term stays. They feature everything you need to make your extended break more comfortable and enjoyable, like air conditioning and kitchens. Some Vrbo holiday homes may also offer discounted weekly or monthly prices, so you can stay longer for less money.
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