Windsor Hills Resort holiday rentals
We found 1,210 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor Hills Resort
Showing deals for:10 Oct - 17 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$3,142
S$3,142
S$449 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$3,374
S$3,374
S$482 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
(113 reviews)
Flexible Cancellation Policy-Upgraded 4-Bed/4 Bath, Pool/Spa 2 Miles to Disney
Kissimmee, FL
8% off
Price is S$3,767
S$3,767
S$538 per night
includes taxes & fees
Image gallery for Enchanting Retreat: A Charming 6-Bd Oasis with Themed Rooms and Pv Pool Bliss
8.68.6 out of 10 rating
Excellent
(37 reviews)
Enchanting Retreat: A Charming 6-Bd Oasis with Themed Rooms and Pv Pool Bliss
Kissimmee, FL
14% off
Price is S$3,007
S$3,007
S$430 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$2,967
S$2,967
S$424 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$2,374
S$2,374
S$339 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$4,519
S$4,519
S$646 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$2,958
S$2,958
S$423 per night
includes taxes & fees
Image gallery for Happy Thoughts Windsor Hills Resort 6BR Villa Private Heated Pool Spa Gameroom
9.49.4 out of 10 rating
Exceptional
(9 reviews)
Happy Thoughts Windsor Hills Resort 6BR Villa Private Heated Pool Spa Gameroom
Kissimmee, FL
7% off
Price is S$3,952
S$3,952
S$565 per night
includes taxes & fees
Image gallery for 7BRThemed - Poolside BBQ - Pool Heat - Near Disney
9.69.6 out of 10 rating
Exceptional
(5 reviews)
7BRThemed - Poolside BBQ - Pool Heat - Near Disney
Kissimmee, FL
7% off
Price is S$3,967
S$3,967
S$567 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$3,028
S$3,028
S$433 per night
includes taxes & fees
Image gallery for Tasteful Themed Windsor Hills Heated Pool Home ~~ Only 3 Miles to Disney World!!
1010 out of 10 rating
Exceptional
(82 reviews)
Tasteful Themed Windsor Hills Heated Pool Home ~~ Only 3 Miles to Disney World!!
Kissimmee, FL
5% off
Price is S$3,879
S$3,879
S$554 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
(119 reviews)
RATED#1 BEST HOME Near Disney! LUXURY 5BEDROOM 5Bath VILLA ,GATED RESORT ,POOL
Kissimmee, FL
7% off
Price is S$2,640
S$2,640
S$377 per night
includes taxes & fees
Image gallery for Top-Rated Amazing Villa! Salt💧Pool, Game Room + Pool Heat, BBQ & Baby Gear
1010 out of 10 rating
Exceptional
(349 reviews)
Top-Rated Amazing Villa! Salt💧Pool, Game Room + Pool Heat, BBQ & Baby Gear
Kissimmee, FL
8% off
Price is S$4,761
S$4,761
S$680 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$3,089
S$3,089
S$441 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$3,967
S$3,967
S$567 per night
includes taxes & fees
Image gallery for Upscale WINDSOR HILLS Private Villa ♥ Pool/Spa, GAME ROOM ♥ 4 mi to DISNEY WORLD
9.89.8 out of 10 rating
Exceptional
(47 reviews)
Upscale WINDSOR HILLS Private Villa ♥ Pool/Spa, GAME ROOM ♥ 4 mi to DISNEY WORLD
Kissimmee, FL
7% off
Price is S$2,618
S$2,618
S$374 per night
includes taxes & fees
Image gallery for Dream Vacation Home at Windsor Hills Resort Homes
9.09.0 out of 10 rating
Wonderful
(12 reviews)
Dream Vacation Home at Windsor Hills Resort Homes
Kissimmee, FL
6% off
Price is S$2,884
S$2,884
S$412 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$2,055
S$2,055
S$294 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
(103 reviews)
Steps from clubhouse. "Be Our Guest" in Windsor Hills-Pool Heat
Kissimmee, FL
7% off
Price is S$2,055
S$2,055
S$294 per night
includes taxes & fees
Image gallery for Fun for kids and parents 6BR/4BA with private pool & hot tub in resort community
9.69.6 out of 10 rating
Exceptional
(65 reviews)
Fun for kids and parents 6BR/4BA with private pool & hot tub in resort community
Kissimmee, FL
7% off
Price is S$2,526
S$2,526
S$361 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
8% off
Price is S$3,052
S$3,052
S$436 per night
includes taxes & fees
Image gallery for ✨CLEAN✨Lux Home✨Pvt Pool✨FREE Waterpark
1010 out of 10 rating
Exceptional
(74 reviews)
✨CLEAN✨Lux Home✨Pvt Pool✨FREE Waterpark
Kissimmee, FL
9% off
Price is S$2,648
S$2,648
S$378 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$2,712
S$2,712
S$387 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: 9 Oct - 12 Oct
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)
The current price is S$804
S$804
for 3 nights, 1 home
S$268 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$1,448
S$1,448
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$1,308
S$1,308
for 3 nights, 1 home
S$436 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$1,478
S$1,478
for 3 nights, 1 home
S$493 per night
includes taxes & fees
Upscale WINDSOR HILLS Private Villa ♥ 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$1,432
S$1,432
for 3 nights, 1 home
S$477 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$1,231
S$1,231
for 3 nights, 1 home
S$410 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