Windsor Hills Resort holiday lettings
We found 1,214 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor Hills Resort
Showing deals for:29 Aug - 5 Sept
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 £3,971
£3,971
£567 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 £2,105
£2,105
£301 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
7% off
Price is £1,737
£1,737
£248 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
(38 reviews)
2 King Ensuite on First Floor with Very Private Pool 5BD/5BA 10% Discount!
Kissimmee, FL
6% off
Price is £1,804
£1,804
£258 per night
includes taxes & fees
Image gallery for Family Wanted: For fun, sun, & making memories! Free BBQ & spa heat too!
9.89.8 out of 10 rating
Exceptional
(109 reviews)
Family Wanted: For fun, sun, & making memories! Free BBQ & spa heat too!
Kissimmee, FL
7% off
Price is £1,822
£1,822
£260 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
(116 reviews)
RATED#1 BEST HOME Near Disney! LUXURY 5BEDROOM 5Bath VILLA ,GATED RESORT ,POOL
Kissimmee, FL
7% off
Price is £1,900
£1,900
£271 per night
includes taxes & fees
Image gallery for Free Pool Heat and BBQ! No Rear Neighbors! South Facing Pool!-AC Game Room!
9.89.8 out of 10 rating
Exceptional
(91 reviews)
Free Pool Heat and BBQ! No Rear Neighbors! South Facing Pool!-AC Game Room!
Kissimmee, FL
9% off
Price is £1,591
£1,591
£227 per night
includes taxes & fees
Image gallery for 🪄✨NEWLY THEMED HARRY POTTER BEDROOM! ✨ LUX REMODEL wPOOL & STEPS TO CLUBHOUSE!
1010 out of 10 rating
Exceptional
(72 reviews)
🪄✨NEWLY THEMED HARRY POTTER BEDROOM! ✨ LUX REMODEL wPOOL & STEPS TO CLUBHOUSE!
Kissimmee, FL
9% off
Price is £1,245
£1,245
£178 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
(44 reviews)
Upscale WINDSOR HILLS Private Villa ♥ Pool/Spa, GAME ROOM ♥ 4 mi to DISNEY WORLD
Kissimmee, FL
7% off
Price is £1,650
£1,650
£236 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 £1,137
£1,137
£162 per night
includes taxes & fees
Image gallery for 6 Bedroom Vacation Home with South Facing Pool in Windsor Hills close to Disney
1010 out of 10 rating
Exceptional
(85 reviews)
6 Bedroom Vacation Home with South Facing Pool in Windsor Hills close to Disney
Kissimmee, FL
7% off
Price is £1,987
£1,987
£284 per night
includes taxes & fees
Image gallery for 4mi to Disneyworld
9.29.2 out of 10 rating
Wonderful
(5 reviews)
4mi to Disneyworld
Kissimmee, FL
7% off
Price is £1,108
£1,108
£158 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
7% off
Price is £1,702
£1,702
£243 per night
includes taxes & fees
Image gallery for Disney Vacation Home with Themed Bedrooms
8.08.0 out of 10 rating
Very good
(18 reviews)
Disney Vacation Home with Themed Bedrooms
Kissimmee, FL
6% off
Price is £1,289
£1,289
£184 per night
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
(227 reviews)
10-20% OFF 5 STAR Top Rated Luxury Disney Adventure Villa @ Windsor Hills Resort
Kissimmee, FL
7% off
Price is £2,307
£2,307
£330 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
(27 reviews)
5 Star Spacious Resort Villa - Pool, Game Room, Near Disney
Kissimmee, FL
7% off
Price is £2,439
£2,439
£348 per night
includes taxes & fees
Image gallery for NEW,Luxury,ThemeParks,5B&BA,Pool,Theater,Arcades,Mario Theme
1010 out of 10 rating
Exceptional
(10 reviews)
NEW,Luxury,ThemeParks,5B&BA,Pool,Theater,Arcades,Mario Theme
Kissimmee, FL
7% off
Price is £1,936
£1,936
£277 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
(102 reviews)
Steps from clubhouse. "Be Our Guest" in Windsor Hills-Pool Heat
Kissimmee, FL
7% off
Price is £1,015
£1,015
£145 per night
includes taxes & fees
Image gallery for Poolside/waterpark in backyard. 1st floor Encanto theme w/Arcade next to Disney!
1010 out of 10 rating
Exceptional
(5 reviews)
Poolside/waterpark in backyard. 1st floor Encanto theme w/Arcade next to Disney!
Kissimmee, FL
7% off
Price is £1,032
£1,032
£147 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
7% off
Price is £784
£784
£112 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, Florida
7% off
Price is £1,685
£1,685
£241 per night
includes taxes & fees
Image gallery for 6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ
9.49.4 out of 10 rating
Exceptional
(229 reviews)
6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ
Kissimmee, FL
8% off
Price is £1,414
£1,414
£202 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 £1,634
£1,634
£233 per night
includes taxes & fees
Image gallery for Windsor Hills - Right at Disney's Doorstep. Universal Studios, SeaWorld.
9.09.0 out of 10 rating
Wonderful
(48 reviews)
Windsor Hills - Right at Disney's Doorstep. Universal Studios, SeaWorld.
Kissimmee, FL
18% off
Price is £749
£749
£107 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
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Cottage
Villa
Chalet
Find the best place to stay - Windsor Hills Resort
Showing deals for: 27 Aug - 30 Aug
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)
The current price is £479
£479
for 3 nights, 1 home
£160 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 £854
£854
for 3 nights, 1 villa
£285 per night
includes taxes & fees
Tequilla Sunrise at Windsor Hills
Sleeps 6 · 3 bedrooms · 3+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
64 reviews(64 reviews)
The current price is £507
£507
for 3 nights, 1 home
£169 per night
includes taxes & fees
RATED#1 BEST HOME Near Disney! LUXURY 5BEDROOM 5Bath VILLA ,GATED RESORT ,POOL
Sleeps 12 · 5 bedrooms · 5 bathrooms
9.49.4 out of 10
Exceptionalexceptional
116 reviews(116 reviews)
The current price is £1,153
£1,153
for 3 nights, 1 villa
£384 per night
includes taxes & fees
Disney World 2 Miles! Family condo
Sleeps 6 · 2 bedrooms · 2 bathrooms
8.88.8 out of 10
Excellentexcellent
31 reviews(31 reviews)
The current price is £407
£407
for 3 nights, 1 apartment
£136 per night
includes taxes & fees
Fabulous Lake View/South Facing Pool Home- Game room -2 Miles to Disney!
Sleeps 10 · 5 bedrooms · 5 bathrooms
8.88.8 out of 10
Excellentexcellent
179 reviews(179 reviews)
The current price is £881
£881
for 3 nights, 1 home
£294 per night
includes taxes & fees
Top rated rentals - Windsor Hills Resort
Fabulous stay
1010 out of 10
Exceptionalexceptional
96 reviews(96 reviews)
Honeymoon and second birthday
1010 out of 10
Exceptionalexceptional
112 reviews(112 reviews)
Great location
1010 out of 10
Exceptionalexceptional
104 reviews(104 reviews)
Sun all Day 5 star stay
1010 out of 10
Exceptionalexceptional
60 reviews(60 reviews)
Birthday trip
1010 out of 10
Exceptionalexceptional
85 reviews(85 reviews)
Great place to stay
1010 out of 10
Exceptionalexceptional
102 reviews(102 reviews)
We loved our stay here
1010 out of 10
Exceptionalexceptional
160 reviews(160 reviews)
Another fantastic stay at Pixie Dust
1010 out of 10
Exceptionalexceptional
79 reviews(79 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, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value