Windsor Hills Resort holiday rentals
We found 1,198 holiday rentals — enter your dates for availability
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 AU$3,854
AU$3,854
AU$551 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 AU$7,820
AU$7,820
AU$1,117 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
8% off
Price is AU$5,262
AU$5,262
AU$752 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 AU$3,624
AU$3,624
AU$518 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 AU$3,806
AU$3,806
AU$544 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 AU$4,438
AU$4,438
AU$634 per night
includes taxes & fees
Image gallery for 7BRThemed - Poolside BBQ - Pool Heat - Near Disney
9.69.6 out of 10 rating
Exceptional
(5 reviews)
7BRThemed - Poolside BBQ - Pool Heat - Near Disney
Kissimmee, FL
8% off
Price is AU$4,426
AU$4,426
AU$632 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 AU$3,020
AU$3,020
AU$431 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 AU$3,097
AU$3,097
AU$442 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 AU$3,051
AU$3,051
AU$436 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 AU$2,280
AU$2,280
AU$326 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 AU$4,303
AU$4,303
AU$615 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 AU$3,567
AU$3,567
AU$510 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 AU$3,396
AU$3,396
AU$485 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 AU$2,096
AU$2,096
AU$299 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
7% off
Price is AU$2,548
AU$2,548
AU$364 per night
includes taxes & fees
Image gallery for Jedi Training Camp Top Rated 5 Star Villa
9.89.8 out of 10 rating
Exceptional
(77 reviews)
Jedi Training Camp Top Rated 5 Star Villa
Kissimmee, Florida
7% off
Price is AU$3,197
AU$3,197
AU$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
(60 reviews)
Sun filled south facing pool & spa with no rear neighbors! Game room!
Kissimmee, FL
7% off
Price is AU$3,068
AU$3,068
AU$438 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 AU$3,111
AU$3,111
AU$444 per night
includes taxes & fees
Image gallery for ✨CLEAN Luxury Retreat wPool✨FREE Waterpark
1010 out of 10 rating
Exceptional
(73 reviews)
✨CLEAN Luxury Retreat wPool✨FREE Waterpark
Kissimmee, FL
9% off
Price is AU$2,759
AU$2,759
AU$394 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
(64 reviews)
Fun for kids and parents 6BR/4BA with private pool & hot tub in resort community
Kissimmee, FL
7% off
Price is AU$2,676
AU$2,676
AU$382 per night
includes taxes & fees
Image gallery for Magical Adv 5 Star Villa Movie Room Arcade Pool and More
9.29.2 out of 10 rating
Wonderful
(13 reviews)
Magical Adv 5 Star Villa Movie Room Arcade Pool and More
Kissimmee, Florida
8% off
Price is AU$3,640
AU$3,640
AU$520 per night
includes taxes & fees
Image gallery for Disney World 2 Miles! Family condo
8.88.8 out of 10 rating
Excellent
(31 reviews)
Disney World 2 Miles! Family condo
Kissimmee, FL
6% off
Price is AU$1,562
AU$1,562
AU$223 per night
includes taxes & fees
Image gallery for Resort Style Living 2 miles from Disney World
9.29.2 out of 10 rating
Wonderful
(93 reviews)
Resort Style Living 2 miles from Disney World
Kissimmee, FL
7% off
Price is AU$1,737
AU$1,737
AU$248 per night
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
93 reviews(93 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
64 reviews(64 reviews)
Once Upon A Dream Villa, a beautiful 6 bed / 4 bath home in Windsor Hills Resort
Sleeps 14 · 6 bedrooms · 4 bathrooms
9.29.2 out of 10
Wonderfulwonderful
103 reviews(103 reviews)
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)
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