Windsor Hills Resort holiday lettings
We found 1,211 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 £3,973
£3,973
£568 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 £1,850
£1,850
£264 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 £1,738
£1,738
£248 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 £1,815
£1,815
£259 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 £1,986
£1,986
£284 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 £1,553
£1,553
£222 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 £1,159
£1,159
£166 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 £1,592
£1,592
£227 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 £1,443
£1,443
£206 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 £1,640
£1,640
£234 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 £1,383
£1,383
£198 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 £1,099
£1,099
£157 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 £2,278
£2,278
£325 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 £1,096
£1,096
£157 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 £865
£865
£124 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 £1,864
£1,864
£266 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 £1,142
£1,142
£163 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 £1,276
£1,276
£182 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 £2,185
£2,185
£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 £1,409
£1,409
£201 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 £1,024
£1,024
£146 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 £1,890
£1,890
£270 per night
includes taxes & fees
Image gallery for Villa 7748 - Arcade Rm Updated Mar 2025! 3 mi from Disney, Pool Heat, BBQ & PS5
1010 out of 10 rating
Exceptional
(63 reviews)
Villa 7748 - Arcade Rm Updated Mar 2025! 3 mi from Disney, Pool Heat, BBQ & PS5
Kissimmee, FL
7% off
Price is £2,058
£2,058
£294 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 £795
£795
£114 per night
includes taxes & fees
Find spaces that suit your style
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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)
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)
*NEW* Windsor Hills - Ohana Oasis Pool Home Near Disney 4bd/4ba
Sleeps 9 · 4 bedrooms · 4 bathrooms
9.69.6 out of 10
Exceptionalexceptional
18 reviews(18 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
102 reviews(102 reviews)
Tequilla Sunrise at Windsor Hills
Sleeps 6 · 3 bedrooms · 3+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
64 reviews(64 reviews)
Top rated rentals - Windsor Hills Resort
Netherland
1010 out of 10
Exceptionalexceptional
112 reviews(112 reviews)
Lovely holiday home
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Honeymoon and second birthday
1010 out of 10
Exceptionalexceptional
112 reviews(112 reviews)
Birthday trip
1010 out of 10
Exceptionalexceptional
85 reviews(85 reviews)
Great place to stay
1010 out of 10
Exceptionalexceptional
103 reviews(103 reviews)
Spacious, comfortable and well equipped house
1010 out of 10
Exceptionalexceptional
232 reviews(232 reviews)
Great Stay
1010 out of 10
Exceptionalexceptional
156 reviews(156 reviews)
Wonderful stay!
1010 out of 10
Exceptionalexceptional
169 reviews(169 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