Windsor Hills Resort holiday rentals
We found 1,207 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor Hills Resort
Showing deals for:15 Aug - 22 Aug
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 S$6,767
S$6,767
S$967 per night
includes taxes & fees
Image gallery for Spacious 5BR Villa with Frozen Room Downstairs Suite for Multigenerational Stays
1010 out of 10 rating
Exceptional
(5 reviews)
Spacious 5BR Villa with Frozen Room Downstairs Suite for Multigenerational Stays
Kissimmee, FL
7% off
Price is S$3,713
S$3,713
S$530 per night
includes taxes & fees
Image gallery for Where Jolly Delight and Magical Memories Unite
1010 out of 10 rating
Exceptional
(104 reviews)
Where Jolly Delight and Magical Memories Unite
Kissimmee, FL
7% off
Price is S$3,427
S$3,427
S$490 per night
includes taxes & 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 S$3,597
S$3,597
S$514 per night
includes taxes & 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
(116 reviews)
RATED#1 BEST HOME Near Disney! LUXURY 5BEDROOM 5Bath VILLA ,GATED RESORT ,POOL
Kissimmee, FL
7% off
Price is S$3,714
S$3,714
S$531 per night
includes taxes & fees
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
7% off
Price is S$4,020
S$4,020
S$574 per night
includes taxes & 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
7% off
Price is S$3,126
S$3,126
S$447 per night
includes taxes & 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
7% off
Price is S$2,089
S$2,089
S$298 per night
includes taxes & 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
6% off
Price is S$3,088
S$3,088
S$441 per night
includes taxes & fees
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
7% off
Price is S$2,975
S$2,975
S$425 per night
includes taxes & fees
Image gallery for 4mi to Disneyworld
9.29.2 out of 10 rating
Wonderful
(5 reviews)
4mi to Disneyworld
Kissimmee, FL
7% off
Price is S$2,333
S$2,333
S$333 per night
includes taxes & fees
Image gallery for ☀️6 BED VILLA - POOL & SPA - BBQ - GAMES ROOM -MILITARY DISCOUNT All DAY SUN
9.69.6 out of 10 rating
Exceptional
(111 reviews)
☀️6 BED VILLA - POOL & SPA - BBQ - GAMES ROOM -MILITARY DISCOUNT All DAY SUN
Kissimmee, FL
7% off
Price is S$3,093
S$3,093
S$442 per night
includes taxes & fees
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
7% off
Price is S$4,085
S$4,085
S$584 per night
includes taxes & fees
Image gallery for Contemporary Disney Villa Minutes from Attractions
9.69.6 out of 10 rating
Exceptional
(20 reviews)
Contemporary Disney Villa Minutes from Attractions
Kissimmee, FL
7% off
Price is S$3,741
S$3,741
S$534 per night
includes taxes & fees
Image gallery for Stunning 6BR Villa with Pvt Pool, Outdoor Kitchen, and Entertainment Paradise
9.69.6 out of 10 rating
Exceptional
(32 reviews)
Stunning 6BR Villa with Pvt Pool, Outdoor Kitchen, and Entertainment Paradise
Kissimmee, FL
6% off
Price is S$3,392
S$3,392
S$485 per night
includes taxes & 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
7% off
Price is S$1,981
S$1,981
S$283 per night
includes taxes & 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 S$4,104
S$4,104
S$586 per night
includes taxes & 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 S$3,270
S$3,270
S$467 per night
includes taxes & fees
Image gallery for Resort Style Living 2 miles from Disney World
9.29.2 out of 10 rating
Wonderful
(93 reviews)
Resort Style Living 2 miles from Disney World
Kissimmee, FL
8% off
Price is S$1,482
S$1,482
S$212 per night
includes taxes & fees
Image gallery for Ground Floor 3BR Condo Steps to Pool Ideal for Seniors Families Near Disney
9.89.8 out of 10 rating
Exceptional
(26 reviews)
Ground Floor 3BR Condo Steps to Pool Ideal for Seniors Families Near Disney
Kissimmee, FL
7% off
Price is S$1,900
S$1,900
S$271 per night
includes taxes & fees
Image gallery for 3 mile to Disney, South facing pool with spa, Free wifi, 6 br/4 full bathroom
9.49.4 out of 10 rating
Exceptional
(25 reviews)
3 mile to Disney, South facing pool with spa, Free wifi, 6 br/4 full bathroom
Kissimmee, FL
5% off
Price is S$2,660
S$2,660
S$380 per night
includes taxes & fees
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
15% off
Price is S$2,524
S$2,524
S$361 per night
includes taxes & fees
Image gallery for Amazing 6-bedroom Villa with Private Pool Minutes from Disney! 5 Star Theming!
1010 out of 10 rating
Exceptional
(38 reviews)
Amazing 6-bedroom Villa with Private Pool Minutes from Disney! 5 Star Theming!
Kissimmee, FL
8% off
Price is S$4,125
S$4,125
S$589 per night
includes taxes & fees
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
Price is S$3,228
S$3,228
S$461 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Windsor Hills Resort
Showing deals for: 13 Aug - 16 Aug
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 S$781
S$781
for 3 nights, 1 home
S$260 per night
includes taxes & fees
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
116 reviews(116 reviews)
The current price is S$1,991
S$1,991
for 3 nights, 1 villa
S$664 per night
includes taxes & fees
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 S$1,479
S$1,479
for 3 nights, 1 villa
S$493 per night
includes taxes & fees
Newly Remodeled & Furnished! Largest Windsor Hills Condo!Kid-Friendly Water Park
Sleeps 7 · 3 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
111 reviews(111 reviews)
The current price is S$793
S$793
for 3 nights, 1 apartment
S$264 per night
includes taxes & fees
Disney World 2 Miles! Family condo
Sleeps 6 · 2 bedrooms · 2 bathrooms
8.88.8 out of 10
Excellentexcellent
31 reviews(31 reviews)
The current price is S$712
S$712
for 3 nights, 1 apartment
S$237 per night
includes taxes & fees
Disney World... Minutes Away! Luxury 6 BR/4 BA 5 Star Villa in Winds
Sleeps 12 · 6 bedrooms · 4 bathrooms
8.08.0 out of 10
Very goodvery good
69 reviews(69 reviews)
The current price is S$1,520
S$1,520
for 3 nights, 1 villa
S$507 per night
includes taxes & fees
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value