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:Sep 12 - Sep 19
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
Price is $683
$683
$4,780 for 7 nights
$4,780 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
(14 reviews)
☆ Location matters! Private palm paradise view from pool - 1 block to waterpark
Kissimmee, FL
8% off
Price is $324
$324
$2,265 for 7 nights
$2,265 for 7 nights
All fees included
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
8% off
Price is $262
$262
$1,831 for 7 nights
$1,831 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
(38 reviews)
2 King Ensuite on First Floor with Very Private Pool 5BD/5BA 10% Discount!
Kissimmee, FL
7% off
Price is $267
$267
$1,866 for 7 nights
$1,866 for 7 nights
All fees included
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 $310
$310
$2,170 for 7 nights
$2,170 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
(91 reviews)
Free Pool Heat and BBQ! No Rear Neighbors! South Facing Pool!-AC Game Room!
Kissimmee, FL
10% off
Price is $252
$252
$1,765 for 7 nights
$1,765 for 7 nights
All fees included
Image gallery for ✨Remodeled Luxury Retreat with Pool-Steps to Clubhouse! 🪄NEW Harry Potter Room!✨
1010 out of 10 rating
Exceptional
(72 reviews)
✨Remodeled Luxury Retreat with Pool-Steps to Clubhouse! 🪄NEW Harry Potter Room!✨
Kissimmee, FL
8% off
Price is $194
$194
$1,357 for 7 nights
$1,357 for 7 nights
All fees included
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
8% off
Price is $306
$306
$2,141 for 7 nights
$2,141 for 7 nights
All fees included
Image gallery for 6 Bed Villa, Pool & Spa, Games Room, Themed Bedroom JULY 4TH AVAILABILITY 🇺🇸
9.69.6 out of 10 rating
Exceptional
(111 reviews)
6 Bed Villa, Pool & Spa, Games Room, Themed Bedroom JULY 4TH AVAILABILITY 🇺🇸
Kissimmee, FL
8% off
Price is $280
$280
$1,957 for 7 nights
$1,957 for 7 nights
All fees included
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
Price is $342
$342
$2,391 for 7 nights
$2,391 for 7 nights
All fees included
Image gallery for FREE: Waterpark, South facing pool, Game room, Themed rooms, 2 Miles to Disney.
9.69.6 out of 10 rating
Exceptional
(138 reviews)
FREE: Waterpark, South facing pool, Game room, Themed rooms, 2 Miles to Disney.
Kissimmee, FL
9% off
Price is $254
$254
$1,776 for 7 nights
$1,776 for 7 nights
All fees included
Image gallery for 4mi to Disneyworld
9.29.2 out of 10 rating
Wonderful
(5 reviews)
4mi to Disneyworld
Kissimmee, FL
8% off
Price is $183
$183
$1,282 for 7 nights
$1,282 for 7 nights
All fees included
Image gallery for Star Wars Themed BR Free Resort Waterpark and Pool Heat 2.5 miles to Disney
1010 out of 10 rating
Exceptional
(36 reviews)
Star Wars Themed BR Free Resort Waterpark and Pool Heat 2.5 miles to Disney
Kissimmee, FL
8% off
Price is $185
$185
$1,298 for 7 nights
$1,298 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 $362
$362
$2,535 for 7 nights
$2,535 for 7 nights
All fees included
Image gallery for 5 Star Spacious Resort Villa - Pool, Game Room, Near Disney
9.69.6 out of 10 rating
Exceptional
(27 reviews)
5 Star Spacious Resort Villa - Pool, Game Room, Near Disney
Kissimmee, FL
8% off
Price is $359
$359
$2,510 for 7 nights
$2,510 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
(60 reviews)
Sun filled south facing pool & spa with no rear neighbors! Game room!
Kissimmee, FL
8% off
Price is $303
$303
$2,118 for 7 nights
$2,118 for 7 nights
All fees included
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
8% off
Price is $185
$185
$1,295 for 7 nights
$1,295 for 7 nights
All fees included
Image gallery for Casa Mickey 3-bed Townhome near Disney with private Splash Pool in Windsor Hills
9.09.0 out of 10 rating
Wonderful
(43 reviews)
Casa Mickey 3-bed Townhome near Disney with private Splash Pool in Windsor Hills
Kissimmee, FL
8% off
Price is $156
$156
$1,094 for 7 nights
$1,094 for 7 nights
All fees included
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 $293
$293
$2,049 for 7 nights
$2,049 for 7 nights
All fees included
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 $295
$295
$2,067 for 7 nights
$2,067 for 7 nights
All fees included
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
Price is $266
$266
$1,861 for 7 nights
$1,861 for 7 nights
All fees included
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
8% off
Price is $166
$166
$1,161 for 7 nights
$1,161 for 7 nights
All fees included
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 $144
$144
$1,009 for 7 nights
$1,009 for 7 nights
All fees included
Image gallery for Lake View and Top floor on Disney's doorstep - Great location
9.89.8 out of 10 rating
Exceptional
(50 reviews)
Lake View and Top floor on Disney's doorstep - Great location
Kissimmee, FL
8% off
Price is $163
$163
$1,142 for 7 nights
$1,142 for 7 nights
All fees included
Find spaces that suit your style
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Find the best place to stay - Windsor Hills Resort
Showing deals for: Sep 12 - Sep 15
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)
The current price is $187
$187
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 $336
$336
All fees included
Tequilla Sunrise at Windsor Hills
Sleeps 6 · 3 bedrooms · 3+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
64 reviews(64 reviews)
The current price is $190
$190
All fees included
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
44 reviews(44 reviews)
The current price is $343
$343
All fees included
Fabulous Lake View/South Facing Pool Home- Game room -2 Miles to Disney!
Sleeps 10 · 5 bedrooms · 5 bathrooms
8.88.8 out of 10
Excellentexcellent
179 reviews(179 reviews)
The current price is $314
$314
All fees included
Welcome To Magnolia Blossom Villa! South Facing Pool in Prime Location.
Sleeps 14 · 6 bedrooms · 4 bathrooms
9.89.8 out of 10
Exceptionalexceptional
50 reviews(50 reviews)
The current price is $333
$333
All fees included
Top rated rentals - Windsor Hills Resort
Amazing place
1010 out of 10
Exceptionalexceptional
62 reviews(62 reviews)
Perfect for short getaway
1010 out of 10
Exceptionalexceptional
44 reviews(44 reviews)
Family vacation
1010 out of 10
Exceptionalexceptional
149 reviews(149 reviews)
Your own Paradise Falls!
1010 out of 10
Exceptionalexceptional
80 reviews(80 reviews)
Coolest House Ever
1010 out of 10
Exceptionalexceptional
66 reviews(66 reviews)
Disney trip
1010 out of 10
Exceptionalexceptional
97 reviews(97 reviews)
Family vacation
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Disney Magic
1010 out of 10
Exceptionalexceptional
161 reviews(161 reviews)