Windsor Hills Resort holiday rentals
We found 1,180 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor Hills Resort
Showing deals for:14 Nov - 21 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$2,832
S$2,832
S$405 nightly
Includes taxes & fees
Image gallery for Our DisneyDreamVilla - Only minutes to DisneyWorld!!!
1010 out of 10 rating
Exceptional
(241 reviews)
Our DisneyDreamVilla - Only minutes to DisneyWorld!!!
Kissimmee, FL
6% off
Price is S$2,694
S$2,694
S$385 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
8% off
Price is S$2,986
S$2,986
S$427 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$6,631
S$6,631
S$947 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
(40 reviews)
10% Discount! 2 King Ensuite on First Floor with Very Private Pool 5BD/5BA
Kissimmee, FL
7% off
Price is S$3,499
S$3,499
S$500 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$2,874
S$2,874
S$411 nightly
Includes taxes & fees
Image gallery for Frozen & Star Wars Fun Near Disney/NICE 7829
8.88.8 out of 10 rating
Excellent
(18 reviews)
Frozen & Star Wars Fun Near Disney/NICE 7829
Kissimmee, FL
7% off
Price is S$2,997
S$2,997
S$428 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$3,026
S$3,026
S$432 nightly
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
18% off
Price is S$2,376
S$2,376
S$339 nightly
Includes taxes & fees
Image gallery for LUXURY WINDSOR HILLS 4/5 BR 5BA POOL HOME 2.5 MILES to DSNY w/ RESORT WATER PARK
9.89.8 out of 10 rating
Exceptional
(151 reviews)
LUXURY WINDSOR HILLS 4/5 BR 5BA POOL HOME 2.5 MILES to DSNY w/ RESORT WATER PARK
Kissimmee, FL
7% off
Price is S$4,073
S$4,073
S$582 nightly
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$4,135
S$4,135
S$591 nightly
Includes taxes & fees
Image gallery for ☆ Location matters! Private palm paradise view from pool - 1 block to waterpark
1010 out of 10 rating
Exceptional
(15 reviews)
☆ Location matters! Private palm paradise view from pool - 1 block to waterpark
Kissimmee, FL
14% off
Price is S$2,940
S$2,940
S$420 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$3,031
S$3,031
S$433 nightly
Includes taxes & fees
Image gallery for 🌟NO CARPETS - ONE LEVEL🌟Newly Renovated Pool/Theater Home In Windsor Hills
9.89.8 out of 10 rating
Exceptional
(135 reviews)
🌟NO CARPETS - ONE LEVEL🌟Newly Renovated Pool/Theater Home In Windsor Hills
Kissimmee, FL
7% off
Price is S$2,739
S$2,739
S$391 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
8% off
Price is S$3,685
S$3,685
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
(56 reviews)
Large Two Story Home with TWO Master Bedrooms with attached full baths.
Kissimmee, FL
7% off
Price is S$3,063
S$3,063
S$438 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$2,608
S$2,608
S$373 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
7% off
Price is S$3,326
S$3,326
S$475 nightly
Includes taxes & fees
Image gallery for Stay near the magic! 3-bedroom home, just 6 minutes to Walt Disney World® Parks!
1010 out of 10 rating
Exceptional
(110 reviews)
Stay near the magic! 3-bedroom home, just 6 minutes to Walt Disney World® Parks!
Kissimmee, FL
7% off
Price is S$1,945
S$1,945
S$278 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$3,012
S$3,012
S$430 nightly
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
(228 reviews)
10-20% OFF 5 STAR Top Rated Luxury Disney Adventure Villa @ Windsor Hills Resort
Kissimmee, FL
8% off
Price is S$3,540
S$3,540
S$506 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
7% off
Price is S$2,665
S$2,665
S$381 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$3,216
S$3,216
S$459 nightly
Includes taxes & fees
Image gallery for 10/10 EXCEPTIONAL RATINGS! Ultra-Clean 3 Bedroom Townhome with Private Pool
1010 out of 10 rating
Exceptional
(115 reviews)
10/10 EXCEPTIONAL RATINGS! Ultra-Clean 3 Bedroom Townhome with Private Pool
Kissimmee, FL
7% off
Price is S$2,593
S$2,593
S$370 nightly
Includes taxes & fees
Find spaces that suit your style
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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)
*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)
Villa The Dreamers , ultra modern villa , 3 miles from Disney , pool
Sleeps 10 · 5 bedrooms · 5 bathrooms
9.69.6 out of 10
Exceptionalexceptional
195 reviews(195 reviews)
TOP-RATED Windsor Hills Home ♥ THEATER ROOM, Game Room, Pool/Spa, 4 Mi to Disney
Sleeps 10 · 5 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
5 reviews(5 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