Windsor Hills Resort holiday lettings
We found 1,199 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor Hills Resort
Showing deals for:5 Sept - 12 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 £3,947
£3,947
£564 per night
includes taxes & fees
Image gallery for 6 bedrooms, pool and game room - 2 miles to Disney
9.29.2 out of 10 rating
Wonderful
(11 reviews)
6 bedrooms, pool and game room - 2 miles to Disney
Kissimmee, FL
7% off
Price is £1,771
£1,771
£253 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 £1,796
£1,796
£257 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 £1,727
£1,727
£247 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 £1,803
£1,803
£258 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 £1,543
£1,543
£220 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 £1,147
£1,147
£164 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 £1,582
£1,582
£226 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 £1,630
£1,630
£233 per night
includes taxes & fees
Image gallery for Where Jolly Delight and Magical Memories Unite
1010 out of 10 rating
Exceptional
(104 reviews)
Where Jolly Delight and Magical Memories Unite
Kissimmee, FL
7% off
Price is £1,973
£1,973
£282 per night
includes taxes & fees
Image gallery for Enchanting Retreat: A Charming 6-Bd Oasis with Themed Rooms and Pv Pool Bliss
8.68.6 out of 10 rating
Excellent
(37 reviews)
Enchanting Retreat: A Charming 6-Bd Oasis with Themed Rooms and Pv Pool Bliss
Kissimmee, FL
13% off
Price is £1,434
£1,434
£205 per night
includes taxes & fees
Image gallery for Wonderful Vacation Villa/Close to Disney, Epcot, Wide World of Sports and Golf
9.89.8 out of 10 rating
Exceptional
(182 reviews)
Wonderful Vacation Villa/Close to Disney, Epcot, Wide World of Sports and Golf
Kissimmee, FL
7% off
Price is £1,375
£1,375
£196 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 £1,091
£1,091
£156 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 £1,089
£1,089
£156 per night
includes taxes & fees
Image gallery for MEMORIAL DAY SALE! Hogwarts Haven! Windsor Hills 3BR, NEXT TO POOL, near Disney!
1010 out of 10 rating
Exceptional
(45 reviews)
MEMORIAL DAY SALE! Hogwarts Haven! Windsor Hills 3BR, NEXT TO POOL, near Disney!
Kissimmee, FL
7% off
Price is £860
£860
£123 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 £2,101
£2,101
£300 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
(36 reviews)
Star Wars Themed BR Free Resort Waterpark and Pool Heat 2.5 miles to Disney
Kissimmee, FL
7% off
Price is £1,122
£1,122
£160 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 £1,852
£1,852
£265 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 £2,183
£2,183
£312 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
7% off
Price is £1,373
£1,373
£196 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 £1,026
£1,026
£147 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 £1,761
£1,761
£252 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 £1,679
£1,679
£240 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 £817
£817
£117 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: 1 Sept - 4 Sept
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 £444
£444
for 3 nights, 1 home
£148 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 £849
£849
for 3 nights, 1 villa
£283 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
63 reviews(63 reviews)
The current price is £633
£633
for 3 nights, 1 home
£211 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 £479
£479
for 3 nights, 1 home
£160 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 £876
£876
for 3 nights, 1 home
£292 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 £404
£404
for 3 nights, 1 apartment
£135 per night
includes taxes & fees
Top rated rentals - Windsor Hills Resort
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1010 out of 10
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Wonderful stay!
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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