Windsor Hills Resort holiday rentals
We found 1,206 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor Hills Resort
Showing deals for:22 Aug - 29 Aug
Image gallery for Spacious 5BR Villa with Frozen Room Downstairs Suite for Multigenerational Stays
1010 out of 10 rating
Exceptional
(5 reviews)
Spacious 5BR Villa with Frozen Room Downstairs Suite for Multigenerational Stays
Kissimmee, FL
7% off
Price is S$3,269
S$3,269
S$467 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
(38 reviews)
2 King Ensuite on First Floor with Very Private Pool 5BD/5BA 10% Discount!
Kissimmee, FL
6% off
Price is S$3,243
S$3,243
S$463 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
(109 reviews)
Family Wanted: For fun, sun, & making memories! Free BBQ & spa heat too!
Kissimmee, FL
7% off
Price is S$2,923
S$2,923
S$418 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
(116 reviews)
RATED#1 BEST HOME Near Disney! LUXURY 5BEDROOM 5Bath VILLA ,GATED RESORT ,POOL
Kissimmee, FL
7% off
Price is S$3,696
S$3,696
S$528 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
7% off
Price is S$3,232
S$3,232
S$462 per night
includes taxes & fees
Image gallery for Guardians Theater 5BR Home Resort w Pool Hot Tub
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Guardians Theater 5BR Home Resort w Pool Hot Tub
Kissimmee, FL
7% off
Price is S$3,999
S$3,999
S$571 per night
includes taxes & fees
Image gallery for Large Two Story Home with TWO Master Bedrooms with attached full baths.
1010 out of 10 rating
Exceptional
(55 reviews)
Large Two Story Home with TWO Master Bedrooms with attached full baths.
Kissimmee, FL
7% off
Price is S$3,110
S$3,110
S$444 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$1,864
S$1,864
S$266 per night
includes taxes & fees
Image gallery for 4mi to Disneyworld
9.29.2 out of 10 rating
Wonderful
(5 reviews)
4mi to Disneyworld
Kissimmee, FL
7% off
Price is S$2,321
S$2,321
S$332 per night
includes taxes & fees
Image gallery for *Great Privacy Backyard*6BR Luxury Villa Pool/Spa
8.08.0 out of 10 rating
Very good
(18 reviews)
*Great Privacy Backyard*6BR Luxury Villa Pool/Spa
Kissimmee, FL
7% off
Price is S$2,752
S$2,752
S$393 per night
includes taxes & fees
Image gallery for ☀️6 BED VILLA - POOL & SPA - BBQ - GAMES ROOM -MILITARY DISCOUNT All DAY SUN
9.69.6 out of 10 rating
Exceptional
(111 reviews)
☀️6 BED VILLA - POOL & SPA - BBQ - GAMES ROOM -MILITARY DISCOUNT All DAY SUN
Kissimmee, FL
8% off
Price is S$3,078
S$3,078
S$440 per night
includes taxes & fees
Image gallery for Paradise Villa 2.5 miles from Disney Gate
1010 out of 10 rating
Exceptional
(21 reviews)
Paradise Villa 2.5 miles from Disney Gate
Kissimmee, FL
7% off
Price is S$3,462
S$3,462
S$495 per night
includes taxes & fees
Image gallery for NEW,Luxury,ThemeParks,5B&BA,Pool,Theater,Arcades,Mario Theme
1010 out of 10 rating
Exceptional
(9 reviews)
NEW,Luxury,ThemeParks,5B&BA,Pool,Theater,Arcades,Mario Theme
Kissimmee, FL
7% off
Price is S$3,582
S$3,582
S$512 per night
includes taxes & fees
Image gallery for Steps from clubhouse. "Be Our Guest" in Windsor Hills-Pool Heat
1010 out of 10 rating
Exceptional
(102 reviews)
Steps from clubhouse. "Be Our Guest" in Windsor Hills-Pool Heat
Kissimmee, FL
7% off
Price is S$1,696
S$1,696
S$242 per night
includes taxes & fees
Image gallery for Contemporary Disney Villa Minutes from Attractions
9.69.6 out of 10 rating
Exceptional
(20 reviews)
Contemporary Disney Villa Minutes from Attractions
Kissimmee, FL
7% off
Price is S$2,972
S$2,972
S$425 per night
includes taxes & fees
Image gallery for Poolside/waterpark in backyard. 1st floor Encanto theme w/Arcade next to Disney!
1010 out of 10 rating
Exceptional
(5 reviews)
Poolside/waterpark in backyard. 1st floor Encanto theme w/Arcade next to Disney!
Kissimmee, FL
7% off
Price is S$1,901
S$1,901
S$272 per night
includes taxes & fees
Image gallery for Windsor Hills Waterpark Community, NEW 2025 Game Room! Pool/Spa, Disney Rooms
1010 out of 10 rating
Exceptional
(8 reviews)
Windsor Hills Waterpark Community, NEW 2025 Game Room! Pool/Spa, Disney Rooms
Kissimmee, FL
5% off
Price is S$2,950
S$2,950
S$421 per night
includes taxes & fees
Image gallery for Flexible Cancellation Policy-Upgraded 4-Bed/4 Bath, Pool/Spa 2 Miles to Disney
1010 out of 10 rating
Exceptional
(112 reviews)
Flexible Cancellation Policy-Upgraded 4-Bed/4 Bath, Pool/Spa 2 Miles to Disney
Kissimmee, FL
8% off
Price is S$4,084
S$4,084
S$583 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
7% off
Price is S$2,950
S$2,950
S$421 per night
includes taxes & fees
Image gallery for Resort Style Living 2 miles from Disney World
9.29.2 out of 10 rating
Wonderful
(93 reviews)
Resort Style Living 2 miles from Disney World
Kissimmee, FL
8% off
Price is S$1,475
S$1,475
S$211 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
15% off
Price is S$2,511
S$2,511
S$359 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$3,211
S$3,211
S$459 per night
includes taxes & fees
Image gallery for Lake View and Top floor on Disney's doorstep - Great location
9.89.8 out of 10 rating
Exceptional
(48 reviews)
Lake View and Top floor on Disney's doorstep - Great location
Kissimmee, FL
7% off
Price is S$1,694
S$1,694
S$242 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$3,323
S$3,323
S$475 per night
includes taxes & fees
Find spaces that suit your style
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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
93 reviews(93 reviews)
RATED#1 BEST HOME Near Disney! LUXURY 5BEDROOM 5Bath VILLA ,GATED RESORT ,POOL
Sleeps 12 · 5 bedrooms · 5 bathrooms
9.49.4 out of 10
Exceptionalexceptional
116 reviews(116 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
18 reviews(18 reviews)
Windsor Hills by Nova
6.06.0 out of 10
2 reviews(2 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)
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
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