Windsor Hills Resort holiday rentals
We found 1,177 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor Hills Resort
Showing deals for:21 Nov - 28 Nov
Image gallery for 6 Bed - 4 Bath Villa SOUTH FACING POOL - 2 Miles From DISNEY - OVER 100 Reviews
9.89.8 out of 10 rating
Exceptional
(128 reviews)
6 Bed - 4 Bath Villa SOUTH FACING POOL - 2 Miles From DISNEY - OVER 100 Reviews
Kissimmee, FL
7% off
Price is S$3,192
S$3,192
S$456 nightly
Includes taxes & fees
Image gallery for Stay in the BEST Luxury 5 bedroom villa with SOUTH facing pool
9.89.8 out of 10 rating
Exceptional
(126 reviews)
Stay in the BEST Luxury 5 bedroom villa with SOUTH facing pool
Kissimmee, FL
7% off
Price is S$3,095
S$3,095
S$442 nightly
Includes taxes & fees
Image gallery for 10% Discount! 2 King Ensuite on First Floor with Very Private Pool 5BD/5BA
9.89.8 out of 10 rating
Exceptional
(41 reviews)
10% Discount! 2 King Ensuite on First Floor with Very Private Pool 5BD/5BA
Kissimmee, FL
7% off
Price is S$4,270
S$4,270
S$610 nightly
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$6,688
S$6,688
S$955 nightly
Includes taxes & fees
Image gallery for Incridible Condo - Just 2 miles from Disney
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Incridible Condo - Just 2 miles from Disney
Kissimmee, FL
7% off
Price is S$2,032
S$2,032
S$290 nightly
Includes taxes & fees
Image gallery for 3 Mi to WDW: Windsor Hills Home w/ Game Room!
9.69.6 out of 10 rating
Exceptional
(86 reviews)
3 Mi to WDW: Windsor Hills Home w/ Game Room!
Kissimmee, FL
7% off
Price is S$2,887
S$2,887
S$412 nightly
Includes taxes & fees
Image gallery for Fun in the Sun at Mickey Hideaway Villa. Make memories & Minutes to Attractions
1010 out of 10 rating
Exceptional
(42 reviews)
Fun in the Sun at Mickey Hideaway Villa. Make memories & Minutes to Attractions
Kissimmee, FL
7% off
Price is S$3,397
S$3,397
S$485 nightly
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
7% off
Price is S$3,614
S$3,614
S$516 nightly
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
(40 reviews)
Amazing 6-bedroom Villa with Private Pool Minutes from Disney! 5 Star Theming!
Kissimmee, FL
8% off
Price is S$4,531
S$4,531
S$647 nightly
Includes taxes & fees
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 S$3,045
S$3,045
S$435 nightly
Includes taxes & fees
Image gallery for Beautiful Sunsets at Windsor Hills 5/5 Home with Overlook & Minutes to the Magic
9.69.6 out of 10 rating
Exceptional
(9 reviews)
Beautiful Sunsets at Windsor Hills 5/5 Home with Overlook & Minutes to the Magic
Kissimmee, FL
7% off
Price is S$4,274
S$4,274
S$611 nightly
Includes taxes & fees
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 S$4,201
S$4,201
S$600 nightly
Includes taxes & fees
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
(74 reviews)
6BR/4B Windsor Hills Villa, Pool & Game Room, 2 Miles from Walt Disney World
Kissimmee, FL
6% off
Price is S$4,092
S$4,092
S$585 nightly
Includes taxes & fees
Image gallery for Sun filled south facing pool & spa with no rear neighbors! Game room!
1010 out of 10 rating
Exceptional
(63 reviews)
Sun filled south facing pool & spa with no rear neighbors! Game room!
Kissimmee, FL
7% off
Price is S$3,134
S$3,134
S$448 nightly
Includes taxes & fees
Image gallery for Elegantly Upgraded 4 bedroom Windsor Hills home with COMPLIMENTARY POOL HEAT!
9.69.6 out of 10 rating
Exceptional
(80 reviews)
Elegantly Upgraded 4 bedroom Windsor Hills home with COMPLIMENTARY POOL HEAT!
Kissimmee, FL
8% off
Price is S$3,680
S$3,680
S$526 nightly
Includes taxes & fees
Image gallery for Large Two Story Home with TWO Master Bedrooms with attached full baths.
1010 out of 10 rating
Exceptional
(57 reviews)
Large Two Story Home with TWO Master Bedrooms with attached full baths.
Kissimmee, FL
7% off
Price is S$3,077
S$3,077
S$440 nightly
Includes taxes & fees
Image gallery for Windsor Hills Resort! 6 Bedroom House, 2 miles to Disney, Private Pool & Spa🏝
1010 out of 10 rating
Exceptional
(23 reviews)
Windsor Hills Resort! 6 Bedroom House, 2 miles to Disney, Private Pool & Spa🏝
Kissimmee, FL
7% off
Price is S$3,885
S$3,885
S$555 nightly
Includes taxes & fees
Image gallery for Announcing Dreams Come True Villa, - Close to clubhouse
1010 out of 10 rating
Exceptional
(17 reviews)
Announcing Dreams Come True Villa, - Close to clubhouse
Kissimmee, FL
7% off
Price is S$4,198
S$4,198
S$600 nightly
Includes taxes & fees
Image gallery for Contemporary Disney Villa Minutes from Attractions
9.69.6 out of 10 rating
Exceptional
(25 reviews)
Contemporary Disney Villa Minutes from Attractions
Kissimmee, FL
8% off
Price is S$5,770
S$5,770
S$824 nightly
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
(69 reviews)
😎RELAX at Windsor Hills🌴, minutes to Disney - 5 bed / 5 bath, Private Pool🌞
Kissimmee, FL
8% off
Price is S$3,177
S$3,177
S$454 nightly
Includes taxes & fees
Image gallery for Superhero Mickey Resort Townhome next to Disney World
9.89.8 out of 10 rating
Exceptional
(12 reviews)
Superhero Mickey Resort Townhome next to Disney World
Kissimmee, FL
7% off
Price is S$1,757
S$1,757
S$251 nightly
Includes taxes & fees
Image gallery for Steps from clubhouse. "Be Our Guest" in Windsor Hills-Pool Heat
1010 out of 10 rating
Exceptional
(104 reviews)
Steps from clubhouse. "Be Our Guest" in Windsor Hills-Pool Heat
Kissimmee, FL
7% off
Price is S$2,051
S$2,051
S$293 nightly
Includes taxes & fees
Image gallery for 5 Star Spacious Resort Villa - Pool, Game Room, Near Disney
9.69.6 out of 10 rating
Exceptional
(28 reviews)
5 Star Spacious Resort Villa - Pool, Game Room, Near Disney
Kissimmee, FL
7% off
Price is S$3,495
S$3,495
S$499 nightly
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
(33 reviews)
Retro 50s 3BR Villa with Pool and Waterpark Access Just 2 Miles from Disney
Kissimmee, FL
7% off
Price is S$2,229
S$2,229
S$318 nightly
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
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)
Villa The Dreamers , ultra modern villa , 3 miles from Disney , pool
Sleeps 10 · 5 bedrooms · 5 bathrooms
9.69.6 out of 10
Exceptionalexceptional
197 reviews(197 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)
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
237 reviews(237 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)
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