Windsor Hills holiday rentals
We found 2,785 holiday rentals — enter your dates for availability
Select from 977 houses, 323 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:3 Oct - 10 Oct
Image gallery for S-Facing Pool, 3.6 mi from Disney, man-gated resort, wheelchair accessible
8.68.6 out of 10 rating
Excellent
(62 reviews)
S-Facing Pool, 3.6 mi from Disney, man-gated resort, wheelchair accessible
Kissimmee, FL
6% off
Price is S$2,167
S$2,167
S$310 per night
includes taxes & fees
Image gallery for Welcome to The new Star, 5 bedrooms , 4 bathrooms southfacing pool and spa
9.29.2 out of 10 rating
Wonderful
(108 reviews)
Welcome to The new Star, 5 bedrooms , 4 bathrooms southfacing pool and spa
Kissimmee, FL
10% off
Price is S$2,401
S$2,401
S$343 per night
includes taxes & fees
Image gallery for Magical Vacation Home with Kid-Themed Rooms 3 Miles from Disney
9.69.6 out of 10 rating
Exceptional
(171 reviews)
Magical Vacation Home with Kid-Themed Rooms 3 Miles from Disney
Kissimmee, FL
7% off
Price is S$2,479
S$2,479
S$354 per night
includes taxes & fees
Image gallery for 5 BR/4 BA Home Newly Remodeled in 2023
9.49.4 out of 10 rating
Exceptional
(91 reviews)
5 BR/4 BA Home Newly Remodeled in 2023
Kissimmee, FL
5% off
Price is S$2,096
S$2,096
S$299 per night
includes taxes & fees
Image gallery for Last-minute special, NEW beds/AC/pool heater/laminate floor, park view!
9.49.4 out of 10 rating
Exceptional
(112 reviews)
Last-minute special, NEW beds/AC/pool heater/laminate floor, park view!
Kissimmee, FL
7% off
Price is S$1,670
S$1,670
S$239 per night
includes taxes & fees
Image gallery for Windsor Palms Villa w/South Facing Private Pool & Hot Tub Close to Disney & Golf
9.89.8 out of 10 rating
Exceptional
(94 reviews)
Windsor Palms Villa w/South Facing Private Pool & Hot Tub Close to Disney & Golf
Kissimmee, FL
7% off
Price is S$1,940
S$1,940
S$277 per night
includes taxes & fees
Image gallery for Spacious Villa with private pool and gameroom ! ( King / King / Queen/ 2 Twins )
9.89.8 out of 10 rating
Exceptional
(87 reviews)
Spacious Villa with private pool and gameroom ! ( King / King / Queen/ 2 Twins )
Kissimmee, FL
7% off
Price is S$2,207
S$2,207
S$315 per night
includes taxes & fees
Image gallery for Private South Facing Pool w/ Jacuzzi & Kiddy pool - 4 bed, 3 bath
1010 out of 10 rating
Exceptional
(31 reviews)
Private South Facing Pool w/ Jacuzzi & Kiddy pool - 4 bed, 3 bath
Kissimmee, FL
5% off
Price is S$2,489
S$2,489
S$356 per night
includes taxes & fees
Image gallery for 3 Miles from Disney!!!!! 4 Bedroom Villa with Private Pool/Game Room
9.89.8 out of 10 rating
Exceptional
(18 reviews)
3 Miles from Disney!!!!! 4 Bedroom Villa with Private Pool/Game Room
Kissimmee, FL
7% off
Price is S$2,368
S$2,368
S$338 per night
includes taxes & fees
Image gallery for Discover magic just 9 mins away! Spacious 5-bed Kissimmee retreat, pool and spa
9.29.2 out of 10 rating
Wonderful
(85 reviews)
Discover magic just 9 mins away! Spacious 5-bed Kissimmee retreat, pool and spa
Kissimmee, FL
9% off
Price is S$2,216
S$2,216
S$317 per night
includes taxes & fees
Image gallery for Mickey's Pool House- Minutes away from Disney World
1010 out of 10 rating
Exceptional
(16 reviews)
Mickey's Pool House- Minutes away from Disney World
Kissimmee, FL
8% off
Price is S$3,248
S$3,248
S$464 per night
includes taxes & fees
Image gallery for ★Amazing Family Getaway | 5min➡️Disney |111
9.09.0 out of 10 rating
Wonderful
(12 reviews)
★Amazing Family Getaway | 5min➡️Disney |111
Kissimmee, FL
6% off
Price is S$2,036
S$2,036
S$291 per night
includes taxes & fees
Image gallery for Luxury vacation home with a pool, just ten minutes from Disney World
9.89.8 out of 10 rating
Exceptional
(175 reviews)
Luxury vacation home with a pool, just ten minutes from Disney World
Kissimmee, FL
7% off
Price is S$2,245
S$2,245
S$321 per night
includes taxes & fees
Image gallery for Welcome to The Coca Cola Villa, 3 miles from Disney World, private pool/spa
9.69.6 out of 10 rating
Exceptional
(216 reviews)
Welcome to The Coca Cola Villa, 3 miles from Disney World, private pool/spa
Kissimmee, FL
10% off
Price is S$2,401
S$2,401
S$343 per night
includes taxes & fees
Image gallery for 5 Star - Always free pool heat and Wifi
9.69.6 out of 10 rating
Exceptional
(138 reviews)
5 Star - Always free pool heat and Wifi
Kissimmee, FL
7% off
Price is S$2,085
S$2,085
S$298 per night
includes taxes & fees
Image gallery for 3 Miles to Disney; Game Room, 100 Yards from Community Center
9.69.6 out of 10 rating
Exceptional
(35 reviews)
3 Miles to Disney; Game Room, 100 Yards from Community Center
Kissimmee, FL
5% off
Price is S$2,534
S$2,534
S$362 per night
includes taxes & fees
Image gallery for 2024-2026- Inquire now for more details and information
9.69.6 out of 10 rating
Exceptional
(107 reviews)
2024-2026- Inquire now for more details and information
Kissimmee, FL
6% off
Price is S$2,095
S$2,095
S$299 per night
includes taxes & fees
Image gallery for 4-bedroom villa just 9 minutes to Walt Disney World® Resort
8.28.2 out of 10 rating
Very good
(10 reviews)
4-bedroom villa just 9 minutes to Walt Disney World® Resort
Kissimmee, FL
15% off
Price is S$1,653
S$1,653
S$236 per night
includes taxes & fees
Image gallery for Welcome to Celebration Villa, 3 miles from Disney World, southfacing pool/spa
9.49.4 out of 10 rating
Exceptional
(244 reviews)
Welcome to Celebration Villa, 3 miles from Disney World, southfacing pool/spa
Kissimmee, FL
10% off
Price is S$2,401
S$2,401
S$343 per night
includes taxes & fees
Image gallery for Welcome to The Magic Modern Castle, 3 miles from Disney World, southfacing pool
9.49.4 out of 10 rating
Exceptional
(248 reviews)
Welcome to The Magic Modern Castle, 3 miles from Disney World, southfacing pool
Kissimmee, FL
10% off
Price is S$2,401
S$2,401
S$343 per night
includes taxes & fees
Image gallery for Welcome to the Story Villa , 3 miles from Disney World, wifi , pool/spa
9.69.6 out of 10 rating
Exceptional
(164 reviews)
Welcome to the Story Villa , 3 miles from Disney World, wifi , pool/spa
Kissimmee, FL
10% off
Price is S$2,401
S$2,401
S$343 per night
includes taxes & fees
Image gallery for Luxurious Pool Villa, Minutes From Walt Disney World
1010 out of 10 rating
Exceptional
(5 reviews)
Luxurious Pool Villa, Minutes From Walt Disney World
Kissimmee, FL
8% off
Price is S$2,595
S$2,595
S$371 per night
includes taxes & fees
Image gallery for South Saltwater Pool/Spa - free pool heat - no rear neighbors- 2 miles to Disney
9.89.8 out of 10 rating
Exceptional
(24 reviews)
South Saltwater Pool/Spa - free pool heat - no rear neighbors- 2 miles to Disney
Kissimmee, FL
7% off
Price is S$6,609
S$6,609
S$944 per night
includes taxes & fees
Image gallery for 4-bedroom vacation home just 8 minutes to Walt Disney World
9.09.0 out of 10 rating
Wonderful
(51 reviews)
4-bedroom vacation home just 8 minutes to Walt Disney World
Kissimmee, FL
6% off
Price is S$2,095
S$2,095
S$299 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
Resort Style Living 2 miles from Disney World
Sleeps 8 · 3 bedrooms · 3 bathrooms
9.29.2 out of 10
Wonderfulwonderful
93 reviews(93 reviews)
Fun for kids and parents 6BR/4BA with private pool & hot tub in resort community
Sleeps 12 · 6 bedrooms · 4 bathrooms
9.69.6 out of 10
Exceptionalexceptional
64 reviews(64 reviews)
Once Upon A Dream Villa, a beautiful 6 bed / 4 bath home in Windsor Hills Resort
Sleeps 14 · 6 bedrooms · 4 bathrooms
9.29.2 out of 10
Wonderfulwonderful
103 reviews(103 reviews)
*NEW* Windsor Hills - Ohana Oasis Pool Home Near Disney 4bd/4ba
Sleeps 9 · 4 bedrooms · 4 bathrooms
9.69.6 out of 10
Exceptionalexceptional
19 reviews(19 reviews)
Newly Updated 4 BR Private Disney Pool Home!
Sleeps 10 · 4 bedrooms · 4 bathrooms
9.49.4 out of 10
Exceptionalexceptional
28 reviews(28 reviews)
Welcome To Magnolia Blossom Villa! South Facing Pool in Prime Location.
Sleeps 14 · 6 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
51 reviews(51 reviews)
Top rated rentals - Windsor Hills
Star wars to the max!
1010 out of 10
Exceptionalexceptional
101 reviews(101 reviews)
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.