Windsor Hills Resort holiday homes
We found 1,191 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor Hills Resort
Showing deals for:7 Nov - 14 Nov
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
(40 reviews)
2 King Ensuite on First Floor with Very Private Pool 5BD/5BA 10% Discount!
Kissimmee, FL
7% off
Price is NZ$4,699
NZ$4,699
NZ$671 per night
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
(125 reviews)
Stay in the BEST Luxury 5 bedroom villa with SOUTH facing pool
Kissimmee, FL
8% off
Price is NZ$3,920
NZ$3,920
NZ$560 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
(15 reviews)
☆ Location matters! Private palm paradise view from pool - 1 block to waterpark
Kissimmee, FL
14% off
Price is NZ$3,524
NZ$3,524
NZ$503 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
(40 reviews)
Amazing 6-bedroom Villa with Private Pool Minutes from Disney! 5 Star Theming!
Kissimmee, FL
8% off
Price is NZ$5,230
NZ$5,230
NZ$747 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
(114 reviews)
Flexible Cancellation Policy-Upgraded 4-Bed/4 Bath, Pool/Spa 2 Miles to Disney
Kissimmee, FL
8% off
Price is NZ$4,952
NZ$4,952
NZ$707 per night
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 NZ$4,368
NZ$4,368
NZ$624 per night
includes taxes & fees
Image gallery for 7BRThemed - Poolside BBQ - Pool Heat - Near Disney
9.89.8 out of 10 rating
Exceptional
(6 reviews)
7BRThemed - Poolside BBQ - Pool Heat - Near Disney
Kissimmee, FL
7% off
Price is NZ$5,936
NZ$5,936
NZ$848 per night
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
(22 reviews)
Windsor Hills Resort! 6 Bedroom House, 2 miles to Disney, Private Pool & Spa🏝
Kissimmee, FL
7% off
Price is NZ$3,955
NZ$3,955
NZ$565 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
(33 reviews)
Retro 50s 3BR Villa with Pool and Waterpark Access Just 2 Miles from Disney
Kissimmee, FL
7% off
Price is NZ$3,111
NZ$3,111
NZ$444 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
(56 reviews)
Large Two Story Home with TWO Master Bedrooms with attached full baths.
Kissimmee, FL
7% off
Price is NZ$4,022
NZ$4,022
NZ$575 per night
includes taxes & fees
Image gallery for Our DisneyDreamVilla - Only minutes to DisneyWorld!!!
1010 out of 10 rating
Exceptional
(240 reviews)
Our DisneyDreamVilla - Only minutes to DisneyWorld!!!
Kissimmee, FL
6% off
Price is NZ$3,538
NZ$3,538
NZ$505 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
8% off
Price is NZ$5,809
NZ$5,809
NZ$830 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
(69 reviews)
😎RELAX at Windsor Hills🌴, minutes to Disney - 5 bed / 5 bath, Private Pool🌞
Kissimmee, FL
8% off
Price is NZ$3,630
NZ$3,630
NZ$519 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 NZ$2,663
NZ$2,663
NZ$380 per night
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 NZ$3,981
NZ$3,981
NZ$569 per night
includes taxes & fees
Image gallery for Life is short...Bring the whole family!
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Life is short...Bring the whole family!
Kissimmee, FL
7% off
Price is NZ$3,992
NZ$3,992
NZ$570 per night
includes taxes & fees
Image gallery for Dream Vacation Home at Windsor Hills Resort Homes
9.09.0 out of 10 rating
Wonderful
(13 reviews)
Dream Vacation Home at Windsor Hills Resort Homes
Kissimmee, FL
6% off
Price is NZ$3,529
NZ$3,529
NZ$504 per night
includes taxes & fees
Image gallery for Jedi Training Camp Top Rated 5 Star Villa
9.89.8 out of 10 rating
Exceptional
(78 reviews)
Jedi Training Camp Top Rated 5 Star Villa
Kissimmee, Florida
8% off
Price is NZ$4,139
NZ$4,139
NZ$591 per night
includes taxes & fees
Image gallery for Star Wars Themed BR Free Resort Waterpark and Pool Heat 2.5 miles to Disney
1010 out of 10 rating
Exceptional
(38 reviews)
Star Wars Themed BR Free Resort Waterpark and Pool Heat 2.5 miles to Disney
Kissimmee, FL
8% off
Price is NZ$3,199
NZ$3,199
NZ$457 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
(62 reviews)
Sun filled south facing pool & spa with no rear neighbors! Game room!
Kissimmee, FL
7% off
Price is NZ$3,425
NZ$3,425
NZ$489 per night
includes taxes & fees
Image gallery for Fun for kids and parents 6BR/4BA with private pool & hot tub in resort community
9.69.6 out of 10 rating
Exceptional
(66 reviews)
Fun for kids and parents 6BR/4BA with private pool & hot tub in resort community
Kissimmee, FL
7% off
Price is NZ$3,546
NZ$3,546
NZ$507 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, FL
8% off
Price is NZ$4,603
NZ$4,603
NZ$658 per night
includes taxes & fees
Image gallery for TOP-RATED Windsor Hills Home ♥ THEATER ROOM, Game Room, Pool/Spa, 4 Mi to Disney
1010 out of 10 rating
Exceptional
(5 reviews)
TOP-RATED Windsor Hills Home ♥ THEATER ROOM, Game Room, Pool/Spa, 4 Mi to Disney
Kissimmee, FL
7% off
Price is NZ$3,511
NZ$3,511
NZ$502 per night
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 NZ$4,240
NZ$4,240
NZ$606 per night
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)
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)
Upscale WINDSOR HILLS Private Home ♥ Pool/Spa, GAME ROOM ♥ 4 mi to DISNEY WORLD
Sleeps 11 · 5 bedrooms · 5 bathrooms
9.89.8 out of 10
Exceptionalexceptional
47 reviews(47 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
236 reviews(236 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