Windsor Hills Resort holiday rentals
We found 1,199 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor Hills Resort
Showing deals for:3 Oct - 10 Oct
Image gallery for Dream Disney Family Vacation, Best Resort, 2 Miles To Disney, Space For 8
8.88.8 out of 10 rating
Excellent
(85 reviews)
Dream Disney Family Vacation, Best Resort, 2 Miles To Disney, Space For 8
Kissimmee, FL
7% off
Price is AU$1,559
AU$1,559
AU$223 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$1,565
AU$1,565
AU$224 per night
includes taxes & fees
Image gallery for Mickey's Hangout - Quiet but close to Clubhouse & Pool - Under NEW MANAGEMENT
8.68.6 out of 10 rating
Excellent
(162 reviews)
Mickey's Hangout - Quiet but close to Clubhouse & Pool - Under NEW MANAGEMENT
Kissimmee, FL
7% off
Price is AU$1,587
AU$1,587
AU$227 per night
includes taxes & fees
Image gallery for Hidden Gem less than 2 miles to Disney! NEW FLOORS and much more! 2 bed/2 bath
9.49.4 out of 10 rating
Exceptional
(29 reviews)
Hidden Gem less than 2 miles to Disney! NEW FLOORS and much more! 2 bed/2 bath
Kissimmee, FL
7% off
Price is AU$1,717
AU$1,717
AU$245 per night
includes taxes & fees
Image gallery for Windsor Hills - Large 3BR/2BA - 5 Min to Disney
9.29.2 out of 10 rating
Wonderful
(214 reviews)
Windsor Hills - Large 3BR/2BA - 5 Min to Disney
Kissimmee, FL
7% off
Price is AU$1,731
AU$1,731
AU$247 per night
includes taxes & fees
Image gallery for Resort Style Living 2 miles from Disney World
9.29.2 out of 10 rating
Wonderful
(94 reviews)
Resort Style Living 2 miles from Disney World
Kissimmee, FL
7% off
Price is AU$1,740
AU$1,740
AU$249 per night
includes taxes & fees
Image gallery for 2785 Family apartment located near Disney!
9.29.2 out of 10 rating
Wonderful
(9 reviews)
2785 Family apartment located near Disney!
Kissimmee, FL
7% off
Price is AU$1,742
AU$1,742
AU$249 per night
includes taxes & fees
Image gallery for 2025 Big Summer Blowout! Windsor Hills! 1st Floor-Waterpark! Close to Disney!
1010 out of 10 rating
Exceptional
(16 reviews)
2025 Big Summer Blowout! Windsor Hills! 1st Floor-Waterpark! Close to Disney!
Kissimmee, FL
7% off
Price is AU$1,854
AU$1,854
AU$265 per night
includes taxes & fees
Image gallery for Luxury, Direct Entry Condo 2BR-2BA - Windsor Hills - Only 2 miles to Disney
8.48.4 out of 10 rating
Very good
(7 reviews)
Luxury, Direct Entry Condo 2BR-2BA - Windsor Hills - Only 2 miles to Disney
Kissimmee, FL
7% off
Price is AU$1,861
AU$1,861
AU$266 per night
includes taxes & fees
Image gallery for 5 Stars Resort, 2 Miles To Disney, 3 BD, 3 BA, Private Pool, Free Wifi
9.69.6 out of 10 rating
Exceptional
(127 reviews)
5 Stars Resort, 2 Miles To Disney, 3 BD, 3 BA, Private Pool, Free Wifi
Kissimmee, FL
7% off
Price is AU$1,869
AU$1,869
AU$267 per night
includes taxes & fees
Image gallery for Casa Mickey 3-bed Townhome near Disney with private Splash Pool on Windsor Hills
9.09.0 out of 10 rating
Wonderful
(43 reviews)
Casa Mickey 3-bed Townhome near Disney with private Splash Pool on Windsor Hills
Kissimmee, FL
8% off
Price is AU$1,898
AU$1,898
AU$271 per night
includes taxes & fees
Image gallery for Getaway with Mickey in Windsor Hills!
9.89.8 out of 10 rating
Exceptional
(145 reviews)
Getaway with Mickey in Windsor Hills!
Kissimmee, FL
7% off
Price is AU$1,939
AU$1,939
AU$277 per night
includes taxes & fees
Image gallery for Welcome to Dream Weaver, 3/2 top floor condo with elevators, 3 miles from Disney
9.89.8 out of 10 rating
Exceptional
(81 reviews)
Welcome to Dream Weaver, 3/2 top floor condo with elevators, 3 miles from Disney
Kissimmee, FL
9% off
Price is AU$1,947
AU$1,947
AU$278 per night
includes taxes & fees
Image gallery for Magnolia Style Condo at Windsor Hills with Disney Theme Bunk Room
1010 out of 10 rating
Exceptional
(141 reviews)
Magnolia Style Condo at Windsor Hills with Disney Theme Bunk Room
Kissimmee, FL
7% off
Price is AU$1,984
AU$1,984
AU$283 per night
includes taxes & fees
Image gallery for Lake View and Top floor on Disney's doorstep - Great location
9.89.8 out of 10 rating
Exceptional
(51 reviews)
Lake View and Top floor on Disney's doorstep - Great location
Kissimmee, FL
7% off
Price is AU$1,997
AU$1,997
AU$285 per night
includes taxes & fees
Image gallery for Luxary villa close to disney
9.69.6 out of 10 rating
Exceptional
(15 reviews)
Luxary villa close to disney
Kissimmee, FL
7% off
Price is AU$2,022
AU$2,022
AU$289 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$2,132
AU$2,132
AU$305 per night
includes taxes & fees
Image gallery for High End Disney Condo, Better Known As The Animal Kingdom...
9.89.8 out of 10 rating
Exceptional
(53 reviews)
High End Disney Condo, Better Known As The Animal Kingdom...
Kissimmee, FL
7% off
Price is AU$2,140
AU$2,140
AU$306 per night
includes taxes & fees
Image gallery for Fully Remodeled~Windsor Hills~2.5 Miles from Disney World Main Entrance
1010 out of 10 rating
Exceptional
(158 reviews)
Fully Remodeled~Windsor Hills~2.5 Miles from Disney World Main Entrance
Kissimmee, FL
7% off
Price is AU$2,169
AU$2,169
AU$310 per night
includes taxes & fees
Image gallery for Newly Renovated! Your Disney Getaway! Water slides, pool arcade and more!
9.69.6 out of 10 rating
Exceptional
(150 reviews)
Newly Renovated! Your Disney Getaway! Water slides, pool arcade and more!
Kissimmee, FL
7% off
Price is AU$2,210
AU$2,210
AU$316 per night
includes taxes & fees
Image gallery for **L@@K** Windsor Hills Resort! ~ 3BD/2BA ~ Sleeps 7!
9.89.8 out of 10 rating
Exceptional
(39 reviews)
**L@@K** Windsor Hills Resort! ~ 3BD/2BA ~ Sleeps 7!
Kissimmee, FL
7% off
Price is AU$2,319
AU$2,319
AU$331 per night
includes taxes & fees
Image gallery for You can't get any closer to Disney!!
9.69.6 out of 10 rating
Exceptional
(57 reviews)
You can't get any closer to Disney!!
Kissimmee, FL
7% off
Price is AU$2,327
AU$2,327
AU$332 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$2,414
AU$2,414
AU$345 per night
includes taxes & fees
Image gallery for SUNNY DISNEY ESCAPE: as close to Disney as you can get with the comforts of home
1010 out of 10 rating
Exceptional
(149 reviews)
SUNNY DISNEY ESCAPE: as close to Disney as you can get with the comforts of home
Kissimmee, FL
7% off
Price is AU$2,505
AU$2,505
AU$358 per night
includes taxes & fees
Find spaces that suit your style
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Chalet
Find the best place to stay - Windsor Hills Resort
Showing deals for: 2 Oct - 5 Oct
Resort Style Living 2 miles from Disney World
Sleeps 8 · 3 bedrooms · 3 bathrooms
9.29.2 out of 10
Wonderfulwonderful
94 reviews(94 reviews)
The current price is AU$959
AU$959
for 3 nights, 1 home
AU$320 per night
includes taxes & fees
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)
The current price is AU$1,705
AU$1,705
for 3 nights, 1 villa
AU$568 per night
includes taxes & fees
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)
The current price is AU$1,435
AU$1,435
for 3 nights, 1 home
AU$478 per night
includes taxes & fees
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)
The current price is AU$1,714
AU$1,714
for 3 nights, 1 home
AU$571 per night
includes taxes & fees
Tequilla Sunrise at Windsor Hills
Sleeps 6 · 3 bedrooms · 3+ bathrooms
9.49.4 out of 10
Exceptionalexceptional
65 reviews(65 reviews)
The current price is AU$980
AU$980
for 3 nights, 1 home
AU$327 per night
includes taxes & fees
Windsor Hills Resort Home with Private Pool , 5 Mins from Disney
Sleeps 13 · 7 bedrooms · 4 bathrooms
8.88.8 out of 10
Excellentexcellent
10 reviews(10 reviews)
The current price is AU$1,362
AU$1,362
for 3 nights, 1 home
AU$454 per night
includes taxes & fees
Top rated rentals - Windsor Hills Resort
Great range of bedrooms for everyone
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