Windsor Hills Resort vacation rentals
We found 1,191 vacation rentals — enter your dates for availability
Vacation rentals with weekly discounts - Windsor Hills Resort
Showing deals for:Nov 7 - Nov 14
Image gallery for Our DisneyDreamVilla - Only minutes to DisneyWorld!!!
1010 out of 10 rating
Exceptional
(240 reviews)
Our DisneyDreamVilla - Only minutes to DisneyWorld!!!
Kissimmee, FL
7% off
Price is $277
$277
$1,941 for 7 nights
$1,941 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 $307
$307
$2,152 for 7 nights
$2,152 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 $369
$369
$2,585 for 7 nights
$2,585 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 $388
$388
$2,718 for 7 nights
$2,718 for 7 nights
All fees included
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 $332
$332
$2,322 for 7 nights
$2,322 for 7 nights
All fees included
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
8% off
Price is $354
$354
$2,476 for 7 nights
$2,476 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 $410
$410
$2,871 for 7 nights
$2,871 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
(12 reviews)
6 bedrooms, pool and game room - 2 miles to Disney
Kissimmee, FL
8% off
Price is $320
$320
$2,237 for 7 nights
$2,237 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 $461
$461
$3,230 for 7 nights
$3,230 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 $312
$312
$2,185 for 7 nights
$2,185 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 $408
$408
$2,859 for 7 nights
$2,859 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 $276
$276
$1,934 for 7 nights
$1,934 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 $359
$359
$2,512 for 7 nights
$2,512 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 $343
$343
$2,398 for 7 nights
$2,398 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
(56 reviews)
Large Two Story Home with TWO Master Bedrooms with attached full baths.
Kissimmee, FL
8% off
Price is $315
$315
$2,208 for 7 nights
$2,208 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 $268
$268
$1,879 for 7 nights
$1,879 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 $465
$465
$3,254 for 7 nights
$3,254 for 7 nights
All fees included
Image gallery for Windsor Hills Resort! 6 Bedroom House, 2 miles to Disney, Private Pool & Spa🏝
1010 out of 10 rating
Exceptional
(22 reviews)
Windsor Hills Resort! 6 Bedroom House, 2 miles to Disney, Private Pool & Spa🏝
Kissimmee, FL
7% off
Price is $310
$310
$2,170 for 7 nights
$2,170 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 $285
$285
$1,992 for 7 nights
$1,992 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 $328
$328
$2,298 for 7 nights
$2,298 for 7 nights
All fees included
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
(33 reviews)
Retro 50s 3BR Villa with Pool and Waterpark Access Just 2 Miles from Disney
Kissimmee, FL
8% off
Price is $244
$244
$1,709 for 7 nights
$1,709 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
(103 reviews)
Steps from clubhouse. "Be Our Guest" in Windsor Hills-Pool Heat
Kissimmee, FL
8% off
Price is $201
$201
$1,406 for 7 nights
$1,406 for 7 nights
All fees included
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
(66 reviews)
Fun for kids and parents 6BR/4BA with private pool & hot tub in resort community
Kissimmee, FL
8% off
Price is $275
$275
$1,925 for 7 nights
$1,925 for 7 nights
All fees included
Image gallery for Jedi Training Camp Top Rated 5 Star Villa
9.89.8 out of 10 rating
Exceptional
(78 reviews)
Jedi Training Camp Top Rated 5 Star Villa
Kissimmee, Florida
8% off
Price is $327
$327
$2,286 for 7 nights
$2,286 for 7 nights
All fees included
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
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
97 reviews(97 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)
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
66 reviews(66 reviews)
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)
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
236 reviews(236 reviews)
Top rated rentals - Windsor Hills Resort
Perfect location
1010 out of 10
Exceptionalexceptional
181 reviews(181 reviews)
Beautiful House!
1010 out of 10
Exceptionalexceptional
83 reviews(83 reviews)
Fantastic House
1010 out of 10
Exceptionalexceptional
67 reviews(67 reviews)
July 4th
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
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
139 reviews(139 reviews)
Wonderful
1010 out of 10
Exceptionalexceptional
110 reviews(110 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
