Windsor Hills Resort holiday rentals
We found 1,211 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor Hills Resort
Showing deals for:17 Oct - 24 Oct
Image gallery for Frozen & Star Wars Fun Near Disney/NICE 7829
8.88.8 out of 10 rating
Excellent
(18 reviews)
Frozen & Star Wars Fun Near Disney/NICE 7829
Kissimmee, FL
7% off
Price is S$3,078
S$3,078
S$440 per night
includes taxes & fees
Image gallery for 2 King Ensuite on First Floor with Very Private Pool 5BD/5BA 10% Discount!
9.89.8 out of 10 rating
Exceptional
(40 reviews)
2 King Ensuite on First Floor with Very Private Pool 5BD/5BA 10% Discount!
Kissimmee, FL
6% off
Price is S$3,235
S$3,235
S$462 per night
includes taxes & fees
Image gallery for Villa 2619 - 3 mi from Disney, Free Heated Pool/Spa, BBQ, Game/Theater Rm, & PS5
1010 out of 10 rating
Exceptional
(78 reviews)
Villa 2619 - 3 mi from Disney, Free Heated Pool/Spa, BBQ, Game/Theater Rm, & PS5
Kissimmee, FL
7% off
Price is S$2,928
S$2,928
S$418 per night
includes taxes & fees
Image gallery for ☆ Location matters! Private palm paradise view from pool - 1 block to waterpark
1010 out of 10 rating
Exceptional
(14 reviews)
☆ Location matters! Private palm paradise view from pool - 1 block to waterpark
Kissimmee, FL
7% off
Price is S$3,528
S$3,528
S$504 per night
includes taxes & fees
Image gallery for Family Wanted: For fun, sun, & making memories! Free BBQ & spa heat too!
9.89.8 out of 10 rating
Exceptional
(110 reviews)
Family Wanted: For fun, sun, & making memories! Free BBQ & spa heat too!
Kissimmee, FL
7% off
Price is S$3,238
S$3,238
S$463 per night
includes taxes & fees
Image gallery for New Luxury Townhome at Windsor Hills Resort 2 Miles from Disney
1010 out of 10 rating
Exceptional
(22 reviews)
New Luxury Townhome at Windsor Hills Resort 2 Miles from Disney
Kissimmee, FL
18% off
Price is S$2,376
S$2,376
S$339 per night
includes taxes & fees
Image gallery for Amazing 6-bedroom Villa with Private Pool Minutes from Disney! 5 Star Theming!
1010 out of 10 rating
Exceptional
(40 reviews)
Amazing 6-bedroom Villa with Private Pool Minutes from Disney! 5 Star Theming!
Kissimmee, FL
8% off
Price is S$3,911
S$3,911
S$559 per night
includes taxes & fees
Image gallery for 6 Bedroom Vacation Home with South Facing Pool in Windsor Hills close to Disney
1010 out of 10 rating
Exceptional
(85 reviews)
6 Bedroom Vacation Home with South Facing Pool in Windsor Hills close to Disney
Kissimmee, FL
8% off
Price is S$4,329
S$4,329
S$618 per night
includes taxes & fees
Image gallery for SOUTH FACING 6 BED VILLA - POOL & SPA - GAMES ROOM - THEMED ROOMS - BBQ ☀️☀️☀️
9.69.6 out of 10 rating
Exceptional
(111 reviews)
SOUTH FACING 6 BED VILLA - POOL & SPA - GAMES ROOM - THEMED ROOMS - BBQ ☀️☀️☀️
Kissimmee, FL
8% off
Price is S$3,030
S$3,030
S$433 per night
includes taxes & fees
Image gallery for RATED#1 BEST HOME Near Disney! LUXURY 5BEDROOM 5Bath VILLA ,GATED RESORT ,POOL
9.49.4 out of 10 rating
Exceptional
(118 reviews)
RATED#1 BEST HOME Near Disney! LUXURY 5BEDROOM 5Bath VILLA ,GATED RESORT ,POOL
Kissimmee, FL
7% off
Price is S$2,642
S$2,642
S$377 per night
includes taxes & fees
Image gallery for 6BR/4B Windsor Hills Villa, Pool & Game Room, 2 Miles from Walt Disney World
9.89.8 out of 10 rating
Exceptional
(73 reviews)
6BR/4B Windsor Hills Villa, Pool & Game Room, 2 Miles from Walt Disney World
Kissimmee, FL
8% off
Price is S$3,684
S$3,684
S$526 per night
includes taxes & fees
Image gallery for 😎RELAX at Windsor Hills🌴, minutes to Disney - 5 bed / 5 bath, Private Pool🌞
9.89.8 out of 10 rating
Exceptional
(65 reviews)
😎RELAX at Windsor Hills🌴, minutes to Disney - 5 bed / 5 bath, Private Pool🌞
Kissimmee, FL
8% off
Price is S$2,963
S$2,963
S$423 per night
includes taxes & fees
Image gallery for Family Paradise w/ Pvt Pool, BBQ Grill, Themed Bedrooms, Game Room & Club access
9.29.2 out of 10 rating
Wonderful
(9 reviews)
Family Paradise w/ Pvt Pool, BBQ Grill, Themed Bedrooms, Game Room & Club access
Kissimmee, FL
14% off
Price is S$2,951
S$2,951
S$422 per night
includes taxes & fees
Image gallery for NEW,Luxury,ThemeParks,5B&BA,Pool,Theater,Arcades,Mario Theme
1010 out of 10 rating
Exceptional
(11 reviews)
NEW,Luxury,ThemeParks,5B&BA,Pool,Theater,Arcades,Mario Theme
Kissimmee, FL
7% off
Price is S$4,076
S$4,076
S$582 per night
includes taxes & fees
Image gallery for Retro 50s 3BR Villa with Pool and Waterpark Access Just 2 Miles from Disney
9.89.8 out of 10 rating
Exceptional
(32 reviews)
Retro 50s 3BR Villa with Pool and Waterpark Access Just 2 Miles from Disney
Kissimmee, FL
7% off
Price is S$1,953
S$1,953
S$279 per night
includes taxes & fees
Image gallery for Jedi Training Camp Top Rated 5 Star Villa
9.89.8 out of 10 rating
Exceptional
(77 reviews)
Jedi Training Camp Top Rated 5 Star Villa
Kissimmee, Florida
7% off
Price is S$2,856
S$2,856
S$408 per night
includes taxes & fees
Image gallery for Ultimate Adventure Villa Top Rated 5 Star Disney more
1010 out of 10 rating
Exceptional
(8 reviews)
Ultimate Adventure Villa Top Rated 5 Star Disney more
Kissimmee, Florida
8% off
Price is S$3,706
S$3,706
S$529 per night
includes taxes & fees
Image gallery for 2785 Family apartment located near Disney!
9.29.2 out of 10 rating
Wonderful
(9 reviews)
2785 Family apartment located near Disney!
Kissimmee, FL
7% off
Price is S$2,376
S$2,376
S$339 per night
includes taxes & fees
Image gallery for TOP-RATED Windsor Hills Villa ♥ THEATER ROOM, Game Room, Pool, 4 Mi to Disney
1010 out of 10 rating
Exceptional
(5 reviews)
TOP-RATED Windsor Hills Villa ♥ THEATER ROOM, Game Room, Pool, 4 Mi to Disney
Kissimmee, FL
7% off
Price is S$2,700
S$2,700
S$386 per night
includes taxes & fees
Image gallery for Incridible Condo - Just 2 miles from Disney
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Incridible Condo - Just 2 miles from Disney
Kissimmee, FL
7% off
Price is S$1,401
S$1,401
S$200 per night
includes taxes & fees
Image gallery for 5 Stars Resort, 2 Miles To Disney, 3 BD, 3 BA, Private Pool, Free Wifi
9.69.6 out of 10 rating
Exceptional
(128 reviews)
5 Stars Resort, 2 Miles To Disney, 3 BD, 3 BA, Private Pool, Free Wifi
Kissimmee, FL
7% off
Price is S$1,560
S$1,560
S$223 per night
includes taxes & fees
Image gallery for Sunset view next to Waterpark/Pool. Moana, Beauty&Beast, etc. theme Near Disney.
1010 out of 10 rating
Exceptional
(18 reviews)
Sunset view next to Waterpark/Pool. Moana, Beauty&Beast, etc. theme Near Disney.
Kissimmee, FL
7% off
Price is S$2,211
S$2,211
S$316 per night
includes taxes & fees
Image gallery for Resort Style Living 2 miles from Disney World
9.29.2 out of 10 rating
Wonderful
(94 reviews)
Resort Style Living 2 miles from Disney World
Kissimmee, FL
8% off
Price is S$1,453
S$1,453
S$208 per night
includes taxes & fees
Image gallery for High End Disney Condo, Better Known As The Animal Kingdom...
9.89.8 out of 10 rating
Exceptional
(53 reviews)
High End Disney Condo, Better Known As The Animal Kingdom...
Kissimmee, FL
7% off
Price is S$1,796
S$1,796
S$257 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
Resort Style Living 2 miles from Disney World
Sleeps 8 · 3 bedrooms · 3 bathrooms
9.29.2 out of 10
Wonderfulwonderful
94 reviews(94 reviews)
Florida Vacation Home - Tiffany's Treasure - near Disney - Kissimmee
Sleeps 12 · 6 bedrooms · 4 bathrooms
9.49.4 out of 10
Exceptionalexceptional
36 reviews(36 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)
Upscale WINDSOR HILLS Private Home ♥ Pool/Spa, GAME ROOM ♥ 4 mi to DISNEY WORLD
Sleeps 11 · 5 bedrooms · 5 bathrooms
9.89.8 out of 10
Exceptionalexceptional
47 reviews(47 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)
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
65 reviews(65 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