Windsor Hills Resort vacation rentals
We found 1,210 vacation rentals — enter your dates for availability
Vacation rentals with weekly discounts - Windsor Hills Resort
Showing deals for:Jul 25 - Aug 1
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 $316
$316
$2,710 total
$2,710 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 ☆ 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
10% off
Price is $271
$271
$2,446 total
$2,446 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 $333
$333
$2,844 total
$2,844 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 Where Jolly Delight and Magical Memories Unite
1010 out of 10 rating
Exceptional
(102 reviews)
Where Jolly Delight and Magical Memories Unite
Kissimmee, FL
10% off
Price is $225
$225
$2,184 total
$2,184 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 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 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 $321
$321
$2,785 total
$2,785 total
Image gallery for 6BR/4B Windsor Hills Villa, Pool & Game Room, 2 Miles from Walt Disney World
9.89.8 out of 10 rating
Exceptional
(71 reviews)
6BR/4B Windsor Hills Villa, Pool & Game Room, 2 Miles from Walt Disney World
Kissimmee, FL
5% off
Price is $288
$288
$2,517 total
$2,517 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 $334
$334
$3,039 total
$3,039 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 $158
$158
$1,406 total
$1,406 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 🩱Waterpark 🩳 Themed rooms 🧳 Near Walt Disney World ®️ ✨️ Private pool 💦
9.89.8 out of 10 rating
Exceptional
(32 reviews)
🩱Waterpark 🩳 Themed rooms 🧳 Near Walt Disney World ®️ ✨️ Private pool 💦
Kissimmee, FL
10% off
Price is $209
$209
$1,808 total
$1,808 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 $296
$296
$2,587 total
$2,587 total
Image gallery for Vibrant Frozen & Lion King Disney-Themed Home
9.09.0 out of 10 rating
Wonderful
(7 reviews)
Vibrant Frozen & Lion King Disney-Themed Home
Kissimmee, FL
10% off
Price is $421
$421
$3,787 total
$3,787 total
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
10% off
Price is $209
$209
$1,779 total
$1,779 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 $405
$405
$3,533 total
$3,533 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
$3,956 total
$3,956 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 $336
$336
$2,939 total
$2,939 total
Image gallery for Windsor Hills Resort - Pool View and 2 miles from Disney World!
1010 out of 10 rating
Exceptional
(15 reviews)
Windsor Hills Resort - Pool View and 2 miles from Disney World!
Kissimmee, FL
5% off
Price is $157
$157
$1,358 total
$1,358 total
Image gallery for Happy Thoughts Windsor Hills Resort 6BR Villa Private Heated Pool Spa Gameroom
9.49.4 out of 10 rating
Exceptional
(9 reviews)
Happy Thoughts Windsor Hills Resort 6BR Villa Private Heated Pool Spa Gameroom
Kissimmee, FL
5% off
Price is $278
$278
$2,552 total
$2,552 total
Find spaces that suit your style
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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
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
176 reviews(176 reviews)
Windsor Hills by Nova
Sleeps 12 · 6 bedrooms
6.06.0 out of 10
2 reviews(2 reviews)
Tequilla Sunrise at Windsor Hills
Sleeps 6 · 3 bedrooms · 3+ bathrooms
9.49.4 out of 10
Exceptionalexceptional
63 reviews(63 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
Great place to stay!
1010 out of 10
Exceptionalexceptional
100 reviews(100 reviews)
Amazing STAY!!
1010 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
Family Vacation with Grandparents
1010 out of 10
Exceptionalexceptional
83 reviews(83 reviews)
Quick trip
1010 out of 10
Exceptionalexceptional
147 reviews(147 reviews)
Wonderful Wonderland!
1010 out of 10
Exceptionalexceptional
80 reviews(80 reviews)
Great spot!
1010 out of 10
Exceptionalexceptional
95 reviews(95 reviews)
Spring Break
1010 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
Family Vacation
1010 out of 10
Exceptionalexceptional
1 review(1 review)
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
