Windsor Hills Resort vacation rentals
We found 1,204 vacation rentals — enter your dates for availability
Vacation rentals with weekly discounts - Windsor Hills Resort
Showing deals for:Jul 18 - Jul 25
Image gallery for Luxury Villa 2 miles from Disney
9.69.6 out of 10 rating
Exceptional
(22 reviews)
Luxury Villa 2 miles from Disney
Kissimmee, FL
5% off
Price is $305
$305
$2,628 total
$2,628 total
Image gallery for Where Dreams Come True! - Only few minutes from Disney!
9.29.2 out of 10 rating
Wonderful
(15 reviews)
Where Dreams Come True! - Only few minutes from Disney!
Kissimmee, FL
5% off
Price is $256
$256
$2,246 total
$2,246 total
Image gallery for FROZEN, HARRY POTTER, MICKEY THEMED ROOMS 5 MINUTES FROM DISNEY
1010 out of 10 rating
Exceptional
(23 reviews)
FROZEN, HARRY POTTER, MICKEY THEMED ROOMS 5 MINUTES FROM DISNEY
Kissimmee, FL
5% off
Price is $327
$327
$2,799 total
$2,799 total
Image gallery for South Facing Lux 5bd/5ba Pool Home W/spa & Private View 2mi To Disney!
9.29.2 out of 10 rating
Wonderful
(23 reviews)
South Facing Lux 5bd/5ba Pool Home W/spa & Private View 2mi To Disney!
Kissimmee, FL
5% off
Price is $238
$238
$2,107 total
$2,107 total
Image gallery for GREAT DEALS , STAR WARS, HARRY POTTER, MINIONS THEMED BEDROOMS
1010 out of 10 rating
Exceptional
(51 reviews)
GREAT DEALS , STAR WARS, HARRY POTTER, MINIONS THEMED BEDROOMS
Kissimmee, FL
10% off
Price is $305
$305
$2,627 total
$2,627 total
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
10% off
Price is $354
$354
$3,042 total
$3,042 total
Image gallery for RATED#1 BEST HOME Near Disney! LUXURY 5BEDROOM 5Bath VILLA ,GATED RESORT ,POOL!
9.49.4 out of 10 rating
Exceptional
(114 reviews)
RATED#1 BEST HOME Near Disney! LUXURY 5BEDROOM 5Bath VILLA ,GATED RESORT ,POOL!
Kissimmee, FL
10% off
Price is $293
$293
$2,611 total
$2,611 total
Image gallery for ☆✴2 miles to Disney, W/Free WaterPark, Heated Pool, Hot tub, Game Room🕹 Mickey☆
9.89.8 out of 10 rating
Exceptional
(19 reviews)
☆✴2 miles to Disney, W/Free WaterPark, Heated Pool, Hot tub, Game Room🕹 Mickey☆
Kissimmee, FL
5% off
Price is $157
$157
$1,405 total
$1,405 total
Image gallery for Upscale WINDSOR HILLS Private Home ♥ Pool/Spa, GAME ROOM ♥ 4 mi to DISNEY WORLD!
1010 out of 10 rating
Exceptional
(41 reviews)
Upscale WINDSOR HILLS Private Home ♥ Pool/Spa, GAME ROOM ♥ 4 mi to DISNEY WORLD!
Kissimmee, FL
10% off
Price is $252
$252
$2,224 total
$2,224 total
Image gallery for Guardians Theater 5BR Home Resort w Pool Hot Tub
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Guardians Theater 5BR Home Resort w Pool Hot Tub
Kissimmee, FL
10% off
Price is $315
$315
$2,825 total
$2,825 total
Image gallery for SUMMER SALE! Hogwarts Haven - Universal Epic! Windsor Hills 3BR, near Disney!
1010 out of 10 rating
Exceptional
(42 reviews)
SUMMER SALE! Hogwarts Haven - Universal Epic! Windsor Hills 3BR, near Disney!
Kissimmee, FL
10% off
Price is $179
$179
$1,574 total
$1,574 total
Image gallery for *Great Privacy Backyard*6BR Luxury Villa Pool/Spa
8.08.0 out of 10 rating
Very Good
(18 reviews)
*Great Privacy Backyard*6BR Luxury Villa Pool/Spa
Kissimmee, FL
10% off
Price is $317
$317
$2,885 total
$2,885 total
Image gallery for 4mi to Disneyworld
9.29.2 out of 10 rating
Wonderful
(5 reviews)
4mi to Disneyworld
Kissimmee, FL
10% off
Price is $198
$198
$1,753 total
$1,753 total
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 $302
$302
$2,633 total
$2,633 total
Image gallery for Mickey Star Wars Themed BR Heated Pool Free Resort Waterpark 3 miles to Disney
1010 out of 10 rating
Exceptional
(36 reviews)
Mickey Star Wars Themed BR Heated Pool Free Resort Waterpark 3 miles to Disney
Kissimmee, FL
10% off
Price is $244
$244
$2,073 total
$2,073 total
Image gallery for Family Paradise w/ Pvt Pool, BBQ Grill, Themed Bedrooms, Game Room & Club access
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Family Paradise w/ Pvt Pool, BBQ Grill, Themed Bedrooms, Game Room & Club access
Kissimmee, FL
8% off
Price is $349
$349
$3,040 total
$3,040 total
Image gallery for NEW,Luxury,ThemeParks,5B&BA,Pool,Theater,Arcades,Mario Theme
1010 out of 10 rating
Exceptional
(9 reviews)
NEW,Luxury,ThemeParks,5B&BA,Pool,Theater,Arcades,Mario Theme
Kissimmee, FL
10% off
Price is $411
$411
$3,580 total
$3,580 total
Image gallery for EPIC Renovated Immersive Themed Pool Villa l VR Game Room l 3 miles to Disney
9.89.8 out of 10 rating
Exceptional
(6 reviews)
EPIC Renovated Immersive Themed Pool Villa l VR Game Room l 3 miles to Disney
Kissimmee, FL
5% off
Price is $454
$454
$3,954 total
$3,954 total
Image gallery for Villa 7748 - Arcade Rm Updated Mar 2025! 3 mi from Disney, Pool Heat, BBQ & PS5
1010 out of 10 rating
Exceptional
(61 reviews)
Villa 7748 - Arcade Rm Updated Mar 2025! 3 mi from Disney, Pool Heat, BBQ & PS5
Kissimmee, FL
10% off
Price is $340
$340
$2,989 total
$2,989 total
Image gallery for Happy Thoughts Windsor Hills Resort 6BR Villa Private Heated PoolSpa Gameroom
9.49.4 out of 10 rating
Exceptional
(9 reviews)
Happy Thoughts Windsor Hills Resort 6BR Villa Private Heated PoolSpa Gameroom
Kissimmee, FL
5% off
Price is $287
$287
$2,620 total
$2,620 total
Image gallery for Steps from clubhouse. "Be Our Guest" in Windsor Hills-Pool Heat
1010 out of 10 rating
Exceptional
(100 reviews)
Steps from clubhouse. "Be Our Guest" in Windsor Hills-Pool Heat
Kissimmee, FL
10% off
Price is $205
$205
$1,775 total
$1,775 total
Image gallery for Vibrant, Poolside Condo with Encanto Magic right next to Disney!!
1010 out of 10 rating
Exceptional
(5 reviews)
Vibrant, Poolside Condo with Encanto Magic right next to Disney!!
Kissimmee, FL
10% off
Price is $186
$186
$1,633 total
$1,633 total
Image gallery for Casa Mickey 3-bed Townhome near Disney with private Splash Pool on Windsor Hills
9.09.0 out of 10 rating
Wonderful
(42 reviews)
Casa Mickey 3-bed Townhome near Disney with private Splash Pool on Windsor Hills
Kissimmee, FL
10% off
Price is $144
$144
$1,328 total
$1,328 total
Image gallery for Paradise Villa 2.5 miles from Disney Gate
1010 out of 10 rating
Exceptional
(21 reviews)
Paradise Villa 2.5 miles from Disney Gate
Kissimmee, FL
10% off
Price is $323
$323
$2,816 total
$2,816 total
Find spaces that suit your style
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Cabin
Cottage
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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
91 reviews(91 reviews)
RATED#1 BEST HOME Near Disney! LUXURY 5BEDROOM 5Bath VILLA ,GATED RESORT ,POOL!
Sleeps 12 · 5 bedrooms · 5 bathrooms
9.49.4 out of 10
Exceptionalexceptional
114 reviews(114 reviews)
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
175 reviews(175 reviews)
Tequilla Sunrise at Windsor Hills
Sleeps 6 · 3 bedrooms · 3+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
62 reviews(62 reviews)
Windsor Hills by Nova
Sleeps 12 · 6 bedrooms
6.06.0 out of 10
2 reviews(2 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
18 reviews(18 reviews)
Top rated rentals - Windsor Hills Resort
Wonderful Stay
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Great for families
1010 out of 10
Exceptionalexceptional
73 reviews(73 reviews)
Wonderful Wonderland!
1010 out of 10
Exceptionalexceptional
80 reviews(80 reviews)
Great for a family
1010 out of 10
Exceptionalexceptional
154 reviews(154 reviews)
Awesome experience
1010 out of 10
Exceptionalexceptional
48 reviews(48 reviews)
Spring Break
1010 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
Family Vacation
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Family trip
1010 out of 10
Exceptionalexceptional
97 reviews(97 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
