Windsor Hills Resort holiday homes
We found 1,195 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$4,687
NZ$4,687
NZ$670 per night
includes taxes & fees
Image gallery for Luxury Villa, Themed Rooms, Close to DW, Gated Community!
1010 out of 10 rating
Exceptional
(6 reviews)
Luxury Villa, Themed Rooms, Close to DW, Gated Community!
Kissimmee, FL
14% off
Price is NZ$2,579
NZ$2,579
NZ$368 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 NZ$5,487
NZ$5,487
NZ$784 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$3,910
NZ$3,910
NZ$559 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$3,515
NZ$3,515
NZ$502 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$5,216
NZ$5,216
NZ$745 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$4,356
NZ$4,356
NZ$622 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$5,951
NZ$5,951
NZ$850 per night
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 NZ$3,943
NZ$3,943
NZ$563 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$3,945
NZ$3,945
NZ$564 per night
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 NZ$6,304
NZ$6,304
NZ$901 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$2,990
NZ$2,990
NZ$427 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$4,011
NZ$4,011
NZ$573 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$3,529
NZ$3,529
NZ$504 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$5,778
NZ$5,778
NZ$825 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$3,620
NZ$3,620
NZ$517 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$2,639
NZ$2,639
NZ$377 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$3,971
NZ$3,971
NZ$567 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$3,977
NZ$3,977
NZ$568 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$3,520
NZ$3,520
NZ$503 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, FL
8% off
Price is NZ$4,116
NZ$4,116
NZ$588 per night
includes taxes & fees
Image gallery for Special July 19-Aug14 USD250. Windsor Hills Resort 6-bedroom House with Pool&Spa
9.09.0 out of 10 rating
Wonderful
(111 reviews)
Special July 19-Aug14 USD250. Windsor Hills Resort 6-bedroom House with Pool&Spa
Kissimmee, FL
14% off
Price is NZ$3,501
NZ$3,501
NZ$500 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$3,197
NZ$3,197
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$3,416
NZ$3,416
NZ$488 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