Windsor Hills Resort vacation rentals
We found 1,182 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 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
All fees included
Price is $331
$331
Image gallery for Paradise Villa 2.5 miles from Disney Gate
1010 out of 10 rating
Exceptional
(22 reviews)
Paradise Villa 2.5 miles from Disney Gate
Kissimmee, FL
8% off
$2,143 for 7 nights
$2,143 for 7 nights
All fees included
Price is $306
$306
Image gallery for Elegantly Upgraded 4 bedroom Windsor Hills home with COMPLIMENTARY POOL HEAT!
9.69.6 out of 10 rating
Exceptional
(77 reviews)
Elegantly Upgraded 4 bedroom Windsor Hills home with COMPLIMENTARY POOL HEAT!
Kissimmee, FL
8% off
$2,037 for 7 nights
$2,037 for 7 nights
All fees included
Price is $291
$291
Image gallery for 🏰 Magical 6-Bed Family Villa ✨[FREE Heated Pool, Spa & BBQ] 5 Mins to Disney 🎢
9.89.8 out of 10 rating
Exceptional
(175 reviews)
🏰 Magical 6-Bed Family Villa ✨[FREE Heated Pool, Spa & BBQ] 5 Mins to Disney 🎢
Kissimmee, FL
9% off
$1,801 for 7 nights
$1,801 for 7 nights
All fees included
Price is $257
$257
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
$1,617 for 7 nights
$1,617 for 7 nights
All fees included
Price is $231
$231
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
All fees included
Price is $683
$683
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
$2,558 for 7 nights
$2,558 for 7 nights
All fees included
Price is $365
$365
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
$2,196 for 7 nights
$2,196 for 7 nights
All fees included
Price is $314
$314
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
$1,697 for 7 nights
$1,697 for 7 nights
All fees included
Price is $242
$242
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
$3,359 for 7 nights
$3,359 for 7 nights
All fees included
Price is $480
$480
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
26% off
$1,082 for 7 nights
$1,082 for 7 nights
All fees included
Price is $155
$155
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
All fees included
Price is $342
$342
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
$2,550 for 7 nights
$2,550 for 7 nights
All fees included
Price is $364
$364
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
$2,439 for 7 nights
$2,439 for 7 nights
All fees included
Price is $348
$348
Image gallery for 4th July Availablity- 6-Bed Villa -Pool & Spa - BBQ -Games Room
9.69.6 out of 10 rating
Exceptional
(111 reviews)
4th July Availablity- 6-Bed Villa -Pool & Spa - BBQ -Games Room
Kissimmee, FL
8% off
$2,008 for 7 nights
$2,008 for 7 nights
All fees included
Price is $287
$287
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
$1,831 for 7 nights
$1,831 for 7 nights
All fees included
Price is $262
$262
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
$2,046 for 7 nights
$2,046 for 7 nights
All fees included
Price is $292
$292
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
$2,141 for 7 nights
$2,141 for 7 nights
All fees included
Price is $306
$306
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
$1,830 for 7 nights
$1,830 for 7 nights
All fees included
Price is $261
$261
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
$1,775 for 7 nights
$1,775 for 7 nights
All fees included
Price is $254
$254
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
$1,741 for 7 nights
$1,741 for 7 nights
All fees included
Price is $249
$249
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
$2,146 for 7 nights
$2,146 for 7 nights
All fees included
Price is $307
$307
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
$1,901 for 7 nights
$1,901 for 7 nights
All fees included
Price is $272
$272
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
$1,276 for 7 nights
$1,276 for 7 nights
All fees included
Price is $182
$182
Find spaces that suit your style
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Find the best place to stay - Windsor Hills Resort
Showing deals for: Sep 23 - Sep 26
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 $166
$166
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 $338
$338
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 $233
$233
All fees included
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 $254
$254
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
45 reviews(45 reviews)
The current price is $330
$330
All fees included
Welcome To Magnolia Blossom Villa! South Facing Pool in Prime Location.
Sleeps 14 · 6 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
51 reviews(51 reviews)
The current price is $288
$288
All fees included
Top rated rentals - Windsor Hills Resort
Wonderful Property
1010 out of 10
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Awesome Resort for a Disney Vacation
1010 out of 10
Exceptionalexceptional
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Great Location and Amenities
1010 out of 10
Exceptionalexceptional
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Family vacation
1010 out of 10
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Your own Paradise Falls!
1010 out of 10
Exceptionalexceptional
80 reviews(80 reviews)
Best property manager ever!
1010 out of 10
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5 stars
1010 out of 10
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122 reviews(122 reviews)
Accessibility is important
1010 out of 10
Exceptionalexceptional
136 reviews(136 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
