
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 Paradise Villa 2.5 miles from Disney Gate

1010 out of 10 rating
Exceptional
(23 reviews)
Paradise Villa 2.5 miles from Disney Gate
Kissimmee, FL
7% off
Price is S$3,323
S$3,323
S$475 per night
includes taxes & fees
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$3,111
S$3,111
S$444 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$3,292
S$3,292
S$470 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$2,984
S$2,984
S$426 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 ☆ 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 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$3,969
S$3,969
S$567 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$4,437
S$4,437
S$634 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 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$4,135
S$4,135
S$591 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$2,958
S$2,958
S$423 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$3,015
S$3,015
S$431 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$3,534
S$3,534
S$505 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$2,218
S$2,218
S$317 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
Find spaces that suit your style
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Condo/Apartment
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Cottage
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Chalet
Find the best place to stay - Windsor Hills Resort
Showing deals for: 11 Oct - 14 OctResort Style Living 2 miles from Disney World
Sleeps 8 · 3 bedrooms · 3 bathrooms
9.29.2 out of 10
Wonderfulwonderful
94 reviews(94 reviews)
The current price is S$766
S$766
for 3 nights, 1 home
S$255 per night
includes taxes & fees
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)
The current price is S$1,449
S$1,449
for 3 nights, 1 villa
S$483 per night
includes taxes & fees
*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)
The current price is S$1,213
S$1,213
for 3 nights, 1 home
S$404 per night
includes taxes & fees
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)
The current price is S$1,449
S$1,449
for 3 nights, 1 home
S$483 per night
includes taxes & fees
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)
The current price is S$1,472
S$1,472
for 3 nights, 1 home
S$491 per night
includes taxes & fees
Windsor Hills Resort Home with Private Pool , 5 Mins from Disney
Sleeps 13 · 7 bedrooms · 4 bathrooms
8.88.8 out of 10
Excellentexcellent
10 reviews(10 reviews)
The current price is S$1,217
S$1,217
for 3 nights, 1 home
S$406 per night
includes taxes & fees
- 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