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 26 - Oct 3
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
Includes all 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
8% off
Price is $480
$480
$3,359 for 7 nights
$3,359 for 7 nights
Includes all 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
(118 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
Includes all fees
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 $314
$314
$2,196 for 7 nights
$2,196 for 7 nights
Includes all fees
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
10% off
Price is $220
$220
$1,540 for 7 nights
$1,540 for 7 nights
Includes all fees
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
Includes all fees
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
Price is $261
$261
$1,830 for 7 nights
$1,830 for 7 nights
Includes all fees
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
Includes all fees
Image gallery for 6 BED VILLA - 7 MINUTES TO DISNEY - POOL & SPA - BBQ - GAMES ROOM SOUTH FACING
9.69.6 out of 10 rating
Exceptional
(111 reviews)
6 BED VILLA - 7 MINUTES TO DISNEY - POOL & SPA - BBQ - GAMES ROOM SOUTH FACING
Kissimmee, FL
8% off
Price is $287
$287
$2,008 for 7 nights
$2,008 for 7 nights
Includes all 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
15% off
Price is $243
$243
$1,702 for 7 nights
$1,702 for 7 nights
Includes all 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
8% off
Price is $182
$182
$1,276 for 7 nights
$1,276 for 7 nights
Includes all fees
Image gallery for MEMORIAL DAY SALE! Hogwarts Haven! Windsor Hills 3BR, NEXT TO POOL, near Disney!
1010 out of 10 rating
Exceptional
(45 reviews)
MEMORIAL DAY SALE! Hogwarts Haven! Windsor Hills 3BR, NEXT TO POOL, near Disney!
Kissimmee, FL
8% off
Price is $153
$153
$1,072 for 7 nights
$1,072 for 7 nights
Includes all 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
15% off
Price is $249
$249
$1,746 for 7 nights
$1,746 for 7 nights
Includes all fees
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 $190
$190
$1,332 for 7 nights
$1,332 for 7 nights
Includes all 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 $365
$365
$2,556 for 7 nights
$2,556 for 7 nights
Includes all fees
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 $206
$206
$1,441 for 7 nights
$1,441 for 7 nights
Includes all fees
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 $292
$292
$2,046 for 7 nights
$2,046 for 7 nights
Includes all 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
(63 reviews)
Fun for kids and parents 6BR/4BA with private pool & hot tub in resort community
Kissimmee, FL
7% off
Price is $198
$198
$1,383 for 7 nights
$1,383 for 7 nights
Includes all fees
Image gallery for Magical Adv 5 Star Villa Movie Room Arcade Pool and More
9.29.2 out of 10 rating
Wonderful
(13 reviews)
Magical Adv 5 Star Villa Movie Room Arcade Pool and More
Kissimmee, Florida
8% off
Price is $255
$255
$1,783 for 7 nights
$1,783 for 7 nights
Includes all fees
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 $160
$160
$1,119 for 7 nights
$1,119 for 7 nights
Includes all fees
Image gallery for Flexible Cancellation Policy-Upgraded 4-Bed/4 Bath, Pool/Spa 2 Miles to Disney
1010 out of 10 rating
Exceptional
(112 reviews)
Flexible Cancellation Policy-Upgraded 4-Bed/4 Bath, Pool/Spa 2 Miles to Disney
Kissimmee, FL
8% off
Price is $365
$365
$2,558 for 7 nights
$2,558 for 7 nights
Includes all fees
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 $309
$309
$2,160 for 7 nights
$2,160 for 7 nights
Includes all 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
8% off
Price is $307
$307
$2,152 for 7 nights
$2,152 for 7 nights
Includes all fees
Image gallery for Villa 7748 - Arcade Rm Updated Mar 2025! 3 mi from Disney, Pool Heat, BBQ & PS5
1010 out of 10 rating
Exceptional
(65 reviews)
Villa 7748 - Arcade Rm Updated Mar 2025! 3 mi from Disney, Pool Heat, BBQ & PS5
Kissimmee, FL
8% off
Price is $348
$348
$2,439 for 7 nights
$2,439 for 7 nights
Includes all fees
Find spaces that suit your style
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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
93 reviews(93 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)
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)
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
63 reviews(63 reviews)
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)
Top rated rentals - Windsor Hills Resort
Vacation
1010 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
PERFECTION!
1010 out of 10
Exceptionalexceptional
169 reviews(169 reviews)
Great location
1010 out of 10
Exceptionalexceptional
77 reviews(77 reviews)
Coolest House Ever
1010 out of 10
Exceptionalexceptional
66 reviews(66 reviews)
Wonderful Spring Break!
1010 out of 10
Exceptionalexceptional
102 reviews(102 reviews)
Convenient
1010 out of 10
Exceptionalexceptional
158 reviews(158 reviews)
A perfect stay!
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Wonderful Property
1010 out of 10
Exceptionalexceptional
118 reviews(118 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
