Windsor Hills Resort vacation rentals
We found 1,194 vacation rentals — enter your dates for availability
Vacation rentals with weekly discounts - Windsor Hills Resort
Showing deals for:Oct 31 - Nov 7
Image gallery for Villa 7757 - 3 mi from Disney, Free Heated Pool/Spa, BBQ, Game/Theater Rm, & PS5
9.89.8 out of 10 rating
Exceptional
(99 reviews)
Villa 7757 - 3 mi from Disney, Free Heated Pool/Spa, BBQ, Game/Theater Rm, & PS5
Kissimmee, FL
8% off
Price is $327
$327
$2,288 for 7 nights
$2,288 for 7 nights
All fees included
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 $331
$331
$2,316 for 7 nights
$2,316 for 7 nights
All fees included
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
8% off
Price is $336
$336
$2,353 for 7 nights
$2,353 for 7 nights
All fees included
Image gallery for Stay in the BEST Luxury 5 bedroom villa with SOUTH facing pool
9.89.8 out of 10 rating
Exceptional
(125 reviews)
Stay in the BEST Luxury 5 bedroom villa with SOUTH facing pool
Kissimmee, FL
9% off
Price is $300
$300
$2,103 for 7 nights
$2,103 for 7 nights
All fees included
Image gallery for 6 bedrooms, pool and game room - 2 miles to Disney
9.29.2 out of 10 rating
Wonderful
(11 reviews)
6 bedrooms, pool and game room - 2 miles to Disney
Kissimmee, FL
8% off
Price is $308
$308
$2,153 for 7 nights
$2,153 for 7 nights
All fees included
Image gallery for Flexible Cancellation Policy-Upgraded 4-Bed/4 Bath, Pool/Spa 2 Miles to Disney
1010 out of 10 rating
Exceptional
(114 reviews)
Flexible Cancellation Policy-Upgraded 4-Bed/4 Bath, Pool/Spa 2 Miles to Disney
Kissimmee, FL
8% off
Price is $384
$384
$2,686 for 7 nights
$2,686 for 7 nights
All fees included
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
Price is $236
$236
$1,649 for 7 nights
$1,649 for 7 nights
All fees included
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
Price is $313
$313
$2,194 for 7 nights
$2,194 for 7 nights
All fees included
Image gallery for ☆ Location matters! Private palm paradise view from pool - 1 block to waterpark
1010 out of 10 rating
Exceptional
(15 reviews)
☆ Location matters! Private palm paradise view from pool - 1 block to waterpark
Kissimmee, FL
15% off
Price is $293
$293
$2,054 for 7 nights
$2,054 for 7 nights
All fees included
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 $352
$352
$2,467 for 7 nights
$2,467 for 7 nights
All fees included
Image gallery for Villa 7748 - Arcade Rm Updated Mar 2025! 3 mi from Disney, Pool Heat, BBQ & PS5
1010 out of 10 rating
Exceptional
(67 reviews)
Villa 7748 - Arcade Rm Updated Mar 2025! 3 mi from Disney, Pool Heat, BBQ & PS5
Kissimmee, FL
8% off
Price is $377
$377
$2,642 for 7 nights
$2,642 for 7 nights
All fees included
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
(228 reviews)
10-20% OFF 5 STAR Top Rated Luxury Disney Adventure Villa @ Windsor Hills Resort
Kissimmee, FL
9% off
Price is $354
$354
$2,477 for 7 nights
$2,477 for 7 nights
All fees included
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 $305
$305
$2,136 for 7 nights
$2,136 for 7 nights
All fees included
Image gallery for 7BRThemed - Poolside BBQ - Pool Heat - Near Disney
9.89.8 out of 10 rating
Exceptional
(6 reviews)
7BRThemed - Poolside BBQ - Pool Heat - Near Disney
Kissimmee, FL
8% off
Price is $339
$339
$2,376 for 7 nights
$2,376 for 7 nights
All fees included
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
Price is $360
$360
$2,522 for 7 nights
$2,522 for 7 nights
All fees included
Image gallery for Only 2 Miles 2 Disney-FREE Water Park- Pool-Spa- Game Room-Huge Playhouse & WiFi
9.69.6 out of 10 rating
Exceptional
(139 reviews)
Only 2 Miles 2 Disney-FREE Water Park- Pool-Spa- Game Room-Huge Playhouse & WiFi
Kissimmee, FL
9% off
Price is $243
$243
$1,699 for 7 nights
$1,699 for 7 nights
All fees included
Image gallery for Villa Sonrisa - 5 Bedroom/5 Bath Luxury, Minutes To Disney In Windsor Hills
1010 out of 10 rating
Exceptional
(218 reviews)
Villa Sonrisa - 5 Bedroom/5 Bath Luxury, Minutes To Disney In Windsor Hills
Kissimmee, FL
8% off
Price is $321
$321
$2,245 for 7 nights
$2,245 for 7 nights
All fees included
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 $405
$405
$2,838 for 7 nights
$2,838 for 7 nights
All fees included
Image gallery for Sun filled south facing pool & spa with no rear neighbors! Game room!
1010 out of 10 rating
Exceptional
(62 reviews)
Sun filled south facing pool & spa with no rear neighbors! Game room!
Kissimmee, FL
8% off
Price is $258
$258
$1,806 for 7 nights
$1,806 for 7 nights
All fees included
Image gallery for Free Pool Heat and BBQ! No Rear Neighbors! South Facing Pool!-AC Game Room!
9.89.8 out of 10 rating
Exceptional
(96 reviews)
Free Pool Heat and BBQ! No Rear Neighbors! South Facing Pool!-AC Game Room!
Kissimmee, FL
8% off
Price is $308
$308
$2,159 for 7 nights
$2,159 for 7 nights
All fees included
Image gallery for Contemporary Disney Villa Minutes from Attractions
9.69.6 out of 10 rating
Exceptional
(24 reviews)
Contemporary Disney Villa Minutes from Attractions
Kissimmee, FL
8% off
Price is $281
$281
$1,970 for 7 nights
$1,970 for 7 nights
All fees included
Image gallery for Where Jolly Delight and Magical Memories Unite
1010 out of 10 rating
Exceptional
(108 reviews)
Where Jolly Delight and Magical Memories Unite
Kissimmee, FL
8% off
Price is $342
$342
$2,391 for 7 nights
$2,391 for 7 nights
All fees included
Image gallery for 😎RELAX at Windsor Hills🌴, minutes to Disney - 5 bed / 5 bath, Private Pool🌞
9.89.8 out of 10 rating
Exceptional
(69 reviews)
😎RELAX at Windsor Hills🌴, minutes to Disney - 5 bed / 5 bath, Private Pool🌞
Kissimmee, FL
8% off
Price is $274
$274
$1,917 for 7 nights
$1,917 for 7 nights
All fees included
Image gallery for Upscale WINDSOR HILLS Private Home ♥ Pool/Spa, GAME ROOM ♥ 4 mi to DISNEY WORLD
9.89.8 out of 10 rating
Exceptional
(47 reviews)
Upscale WINDSOR HILLS Private Home ♥ Pool/Spa, GAME ROOM ♥ 4 mi to DISNEY WORLD
Kissimmee, FL
8% off
Price is $263
$263
$1,841 for 7 nights
$1,841 for 7 nights
All fees included
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Find the best place to stay - Windsor Hills Resort
Showing deals for: Oct 31 - Nov 3
Resort Style Living 2 miles from Disney World
Sleeps 8 · 3 bedrooms · 3 bathrooms
9.29.2 out of 10
Wonderfulwonderful
97 reviews(97 reviews)
The current price is $187
$187
$561 for 3 nights
All fees included
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 $349
$349
$1,046 for 3 nights
All fees included
*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 $277
$277
$832 for 3 nights
All fees included
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 $339
$339
$1,018 for 3 nights
All fees included
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 $293
$293
$878 for 3 nights
All fees included
Windsor Hills Private Luxury Pool House, Sleeps 13
Sleeps 13 · 6 bedrooms · 4 bathrooms
9.09.0 out of 10
Wonderfulwonderful
154 reviews(154 reviews)
The current price is $367
$367
$1,102 for 3 nights
All fees included
Top rated rentals - Windsor Hills Resort
Perfect location
1010 out of 10
Exceptionalexceptional
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Beautiful House!
1010 out of 10
Exceptionalexceptional
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Fantastic House
1010 out of 10
Exceptionalexceptional
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July 4th
1010 out of 10
Exceptionalexceptional
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Comrow Street, Kissimmee
1010 out of 10
Exceptionalexceptional
172 reviews(172 reviews)
Excellent Stay
1010 out of 10
Exceptionalexceptional
24 reviews(24 reviews)
Accessibility is important
1010 out of 10
Exceptionalexceptional
138 reviews(138 reviews)
Wonderful
1010 out of 10
Exceptionalexceptional
110 reviews(110 reviews)
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All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
More for lessMore space, more privacy, more amenities — more value
