Windsor Hills Resort vacation rentals
We found 1,199 vacation rentals — enter your dates for availability
Vacation rentals with weekly discounts - Windsor Hills Resort
Showing deals for:Oct 3 - Oct 10
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
$2,315 for 7 nights
$2,315 for 7 nights
Price is $331
$331
Fees included upfront
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
$4,780 for 7 nights
$4,780 for 7 nights
Price is $683
$683
Fees included upfront
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
7% off
$2,138 for 7 nights
$2,138 for 7 nights
Price is $305
$305
Fees included upfront
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
$2,686 for 7 nights
$2,686 for 7 nights
Price is $384
$384
Fees included upfront
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
20% off
$1,648 for 7 nights
$1,648 for 7 nights
Price is $235
$235
Fees included upfront
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
15% off
$1,751 for 7 nights
$1,751 for 7 nights
Price is $250
$250
Fees included upfront
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
8% off
$2,982 for 7 nights
$2,982 for 7 nights
Price is $426
$426
Fees included upfront
Image gallery for Where Jolly Delight and Magical Memories Unite
1010 out of 10 rating
Exceptional
(106 reviews)
Where Jolly Delight and Magical Memories Unite
Kissimmee, FL
8% off
$2,391 for 7 nights
$2,391 for 7 nights
Price is $342
$342
Fees included upfront
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
$2,720 for 7 nights
$2,720 for 7 nights
Price is $389
$389
Fees included upfront
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
$2,136 for 7 nights
$2,136 for 7 nights
Price is $305
$305
Fees included upfront
Image gallery for 10-20% OFF 5 STAR Top Rated Luxury Disney Adventure Villa @ Windsor Hills Resort
9.89.8 out of 10 rating
Exceptional
(227 reviews)
10-20% OFF 5 STAR Top Rated Luxury Disney Adventure Villa @ Windsor Hills Resort
Kissimmee, FL
8% off
$2,517 for 7 nights
$2,517 for 7 nights
Price is $360
$360
Fees included upfront
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
8% off
$2,678 for 7 nights
$2,678 for 7 nights
Price is $383
$383
Fees included upfront
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
8% off
$2,223 for 7 nights
$2,223 for 7 nights
Price is $318
$318
Fees included upfront
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
8% off
$1,831 for 7 nights
$1,831 for 7 nights
Price is $262
$262
Fees included upfront
Image gallery for Sun filled south facing pool & spa with no rear neighbors! Game room!
1010 out of 10 rating
Exceptional
(60 reviews)
Sun filled south facing pool & spa with no rear neighbors! Game room!
Kissimmee, FL
8% off
$1,805 for 7 nights
$1,805 for 7 nights
Price is $258
$258
Fees included upfront
Image gallery for Villa Sonrisa - 5 Bedroom/5 Bath Luxury, Minutes To Disney In Windsor Hills
1010 out of 10 rating
Exceptional
(217 reviews)
Villa Sonrisa - 5 Bedroom/5 Bath Luxury, Minutes To Disney In Windsor Hills
Kissimmee, FL
8% off
$2,254 for 7 nights
$2,254 for 7 nights
Price is $322
$322
Fees included upfront
Image gallery for Upscale WINDSOR HILLS Private Villa ♥ Pool/Spa, GAME ROOM ♥ 4 mi to DISNEY WORLD
1010 out of 10 rating
Exceptional
(45 reviews)
Upscale WINDSOR HILLS Private Villa ♥ Pool/Spa, GAME ROOM ♥ 4 mi to DISNEY WORLD
Kissimmee, FL
8% off
$1,795 for 7 nights
$1,795 for 7 nights
Price is $256
$256
Fees included upfront
Image gallery for Themed Room Lake Retreat Near Disney Magic
8.28.2 out of 10 rating
Very Good
(20 reviews)
Themed Room Lake Retreat Near Disney Magic
Kissimmee, FL
7% off
$1,780 for 7 nights
$1,780 for 7 nights
Price is $254
$254
Fees included upfront
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
$2,808 for 7 nights
$2,808 for 7 nights
Price is $401
$401
Fees included upfront
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
8% off
$1,410 for 7 nights
$1,410 for 7 nights
Price is $201
$201
Fees included upfront
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
15% off
$1,804 for 7 nights
$1,804 for 7 nights
Price is $258
$258
Fees included upfront
Image gallery for Dream Vacation Home at Windsor Hills Resort Homes
9.09.0 out of 10 rating
Wonderful
(11 reviews)
Dream Vacation Home at Windsor Hills Resort Homes
Kissimmee, FL
7% off
$2,032 for 7 nights
$2,032 for 7 nights
Price is $290
$290
Fees included upfront
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
8% off
$2,567 for 7 nights
$2,567 for 7 nights
Price is $367
$367
Fees included upfront
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
8% off
$1,200 for 7 nights
$1,200 for 7 nights
Price is $171
$171
Fees included upfront
Find spaces that suit your style
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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)
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)
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)
Upscale WINDSOR HILLS Private Villa ♥ Pool/Spa, GAME ROOM ♥ 4 mi to DISNEY WORLD
Sleeps 11 · 5 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
45 reviews(45 reviews)
Top rated rentals - Windsor Hills Resort
Family Vacation
1010 out of 10
Exceptionalexceptional
102 reviews(102 reviews)
The best vacation experience ever!
1010 out of 10
Exceptionalexceptional
158 reviews(158 reviews)
Disney family vacation
1010 out of 10
Exceptionalexceptional
63 reviews(63 reviews)
Wonderful Property
1010 out of 10
Exceptionalexceptional
45 reviews(45 reviews)
Highly recommend!
1010 out of 10
Exceptionalexceptional
65 reviews(65 reviews)
Family vacation
1010 out of 10
Exceptionalexceptional
149 reviews(149 reviews)
Nice home, convenient to WDW
1010 out of 10
Exceptionalexceptional
19 reviews(19 reviews)
So good you don’t want to leave!!!
1010 out of 10
Exceptionalexceptional
93 reviews(93 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
More for lessMore space, more privacy, more amenities — more value
