Windsor Hills Resort holiday rentals
We found 1,201 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor Hills Resort
Showing deals for:3 Oct - 10 Oct
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
Price is S$3,261
S$3,261
S$466 per night
includes taxes & fees
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$6,633
S$6,633
S$948 per night
includes taxes & fees
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
(39 reviews)
2 King Ensuite on First Floor with Very Private Pool 5BD/5BA 10% Discount!
Kissimmee, FL
6% off
Price is S$2,976
S$2,976
S$425 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$3,757
S$3,757
S$537 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
14% off
Price is S$2,490
S$2,490
S$356 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
25% off
Price is S$2,137
S$2,137
S$305 per night
includes taxes & fees
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
7% off
Price is S$4,455
S$4,455
S$636 per night
includes taxes & fees
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
7% off
Price is S$3,344
S$3,344
S$478 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
8% off
Price is S$3,020
S$3,020
S$431 per night
includes taxes & fees
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
(227 reviews)
10-20% OFF 5 STAR Top Rated Luxury Disney Adventure Villa @ Windsor Hills Resort
Kissimmee, FL
7% off
Price is S$3,547
S$3,547
S$507 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$3,825
S$3,825
S$546 per night
includes taxes & fees
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
7% off
Price is S$3,163
S$3,163
S$452 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
(118 reviews)
RATED#1 BEST HOME Near Disney! LUXURY 5BEDROOM 5Bath VILLA ,GATED RESORT ,POOL
Kissimmee, FL
7% off
Price is S$2,633
S$2,633
S$376 per night
includes taxes & fees
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
7% off
Price is S$2,896
S$2,896
S$414 per night
includes taxes & fees
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
7% off
Price is S$3,176
S$3,176
S$454 per night
includes taxes & fees
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
7% off
Price is S$2,583
S$2,583
S$369 per night
includes taxes & fees
Image gallery for Top-Rated Amazing Villa! Salt💧Pool, Game Room + Pool Heat, BBQ & Baby Gear
1010 out of 10 rating
Exceptional
(349 reviews)
Top-Rated Amazing Villa! Salt💧Pool, Game Room + Pool Heat, BBQ & Baby Gear
Kissimmee, FL
8% off
Price is S$4,225
S$4,225
S$604 per night
includes taxes & fees
Image gallery for Themed Room Lake Retreat Near Disney Magic
8.28.2 out of 10 rating
Very good
(20 reviews)
Themed Room Lake Retreat Near Disney Magic
Kissimmee, FL
7% off
Price is S$2,548
S$2,548
S$364 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$1,906
S$1,906
S$272 per night
includes taxes & fees
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
14% off
Price is S$2,616
S$2,616
S$374 per night
includes taxes & fees
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
6% off
Price is S$2,876
S$2,876
S$411 per night
includes taxes & fees
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
7% off
Price is S$1,769
S$1,769
S$253 per night
includes taxes & fees
Image gallery for Fully Remodeled in Windsor Hills ~ 2.5 Miles to Disney World Entrance
9.89.8 out of 10 rating
Exceptional
(176 reviews)
Fully Remodeled in Windsor Hills ~ 2.5 Miles to Disney World Entrance
Kissimmee, FL
7% off
Price is S$2,396
S$2,396
S$342 per night
includes taxes & fees
Image gallery for NEW,Luxury,ThemeParks,5B&BA,Pool,Theater,Arcades,Mario Theme
1010 out of 10 rating
Exceptional
(11 reviews)
NEW,Luxury,ThemeParks,5B&BA,Pool,Theater,Arcades,Mario Theme
Kissimmee, FL
7% off
Price is S$3,560
S$3,560
S$509 per night
includes taxes & fees
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
Showing deals for: 27 Sept - 30 Sept
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$763
S$763
for 3 nights, 1 home
S$254 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$1,444
S$1,444
for 3 nights, 1 villa
S$481 per night
includes taxes & fees
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
64 reviews(64 reviews)
The current price is S$1,166
S$1,166
for 3 nights, 1 home
S$389 per night
includes taxes & fees
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 S$1,435
S$1,435
for 3 nights, 1 home
S$478 per night
includes taxes & fees
Tequilla Sunrise at Windsor Hills
Sleeps 6 · 3 bedrooms · 3+ bathrooms
9.49.4 out of 10
Exceptionalexceptional
65 reviews(65 reviews)
The current price is S$848
S$848
for 3 nights, 1 home
S$283 per night
includes taxes & fees
Windsor Hills Resort Home with Private Pool , 5 Mins from Disney
Sleeps 13 · 7 bedrooms · 4 bathrooms
8.88.8 out of 10
Excellentexcellent
9 reviews(9 reviews)
The current price is S$1,163
S$1,163
for 3 nights, 1 home
S$388 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