
Windsor Hills Resort vacation rentals
We found 1,211 vacation rentals — enter your dates for availability
Showing deals for:Oct 17 - Oct 24
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 $312
$312
$2,183 for 7 nights
$2,183 for 7 nights
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
Price is $326
$326
$2,280 for 7 nights
$2,280 for 7 nights
Fees included upfront
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
8% off
Price is $295
$295
$2,062 for 7 nights
$2,062 for 7 nights
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
Price is $359
$359
$2,510 for 7 nights
$2,510 for 7 nights
Fees included upfront
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
8% off
Price is $327
$327
$2,291 for 7 nights
$2,291 for 7 nights
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
Price is $236
$236
$1,649 for 7 nights
$1,649 for 7 nights
Fees included upfront
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 $395
$395
$2,767 for 7 nights
$2,767 for 7 nights
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
Price is $442
$442
$3,093 for 7 nights
$3,093 for 7 nights
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
Price is $305
$305
$2,136 for 7 nights
$2,136 for 7 nights
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
(118 reviews)
RATED#1 BEST HOME Near Disney! LUXURY 5BEDROOM 5Bath VILLA ,GATED RESORT ,POOL
Kissimmee, FL
8% off
Price is $262
$262
$1,832 for 7 nights
$1,832 for 7 nights
Fees included upfront
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 $375
$375
$2,624 for 7 nights
$2,624 for 7 nights
Fees included upfront
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 $298
$298
$2,087 for 7 nights
$2,087 for 7 nights
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
Price is $415
$415
$2,906 for 7 nights
$2,906 for 7 nights
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
Price is $300
$300
$2,102 for 7 nights
$2,102 for 7 nights
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
Price is $194
$194
$1,359 for 7 nights
$1,359 for 7 nights
Fees included upfront
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 $291
$291
$2,037 for 7 nights
$2,037 for 7 nights
Fees included upfront
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 $381
$381
$2,666 for 7 nights
$2,666 for 7 nights
Fees included upfront
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
8% off
Price is $240
$240
$1,677 for 7 nights
$1,677 for 7 nights
Fees included upfront
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
8% off
Price is $267
$267
$1,872 for 7 nights
$1,872 for 7 nights
Fees included upfront
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
8% off
Price is $139
$139
$973 for 7 nights
$973 for 7 nights
Fees included upfront
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
8% off
Price is $155
$155
$1,083 for 7 nights
$1,083 for 7 nights
Fees included upfront
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
8% off
Price is $220
$220
$1,541 for 7 nights
$1,541 for 7 nights
Fees included upfront
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 $144
$144
$1,009 for 7 nights
$1,009 for 7 nights
Fees included upfront
Image gallery for High End Disney Condo, Better Known As The Animal Kingdom...

9.89.8 out of 10 rating
Exceptional
(53 reviews)
High End Disney Condo, Better Known As The Animal Kingdom...
Kissimmee, FL
8% off
Price is $179
$179
$1,250 for 7 nights
$1,250 for 7 nights
Fees included upfront
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Windsor Hills Resort
Showing deals for: Oct 13 - Oct 16Resort 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 $166
$166
Fees included upfront
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 $338
$338
Fees included upfront
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 $324
$324
Fees included upfront
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 $306
$306
Fees included upfront
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 $298
$298
Fees included upfront
6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ
Sleeps 14 · 6 bedrooms · 4 bathrooms
9.49.4 out of 10
Exceptionalexceptional
230 reviews(230 reviews)
The current price is $290
$290
Fees included upfront
Top rated rentals - Windsor Hills Resort
July 4th
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
Wonderful vacation home
1010 out of 10
Exceptionalexceptional
82 reviews(82 reviews)
First Time Orlando. Isit
1010 out of 10
Exceptionalexceptional
72 reviews(72 reviews)
Comrow Street, Kissimmee
1010 out of 10
Exceptionalexceptional
172 reviews(172 reviews)
Highly recommend!
1010 out of 10
Exceptionalexceptional
65 reviews(65 reviews)
Excellent Stay
1010 out of 10
Exceptionalexceptional
24 reviews(24 reviews)
Accessibility is important
1010 out of 10
Exceptionalexceptional
138 reviews(138 reviews)
Absolutely perfect
1010 out of 10
Exceptionalexceptional
5 reviews(5 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