Windsor Hills Resort holiday lettings
We found 1,200 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor Hills Resort
Showing deals for:12 Sept - 19 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 £3,960
£3,960
£566 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 £1,914
£1,914
£273 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 £1,555
£1,555
£222 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 £1,566
£1,566
£224 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
(110 reviews)
Family Wanted: For fun, sun, & making memories! Free BBQ & spa heat too!
Kissimmee, FL
7% off
Price is £1,809
£1,809
£258 per night
includes taxes & fees
Image gallery for Magical retreat just 4 miles from Disney World with Private Pool and Game Room!
9.89.8 out of 10 rating
Exceptional
(13 reviews)
Magical retreat just 4 miles from Disney World with Private Pool and Game Room!
Kissimmee, FL
7% off
Price is £2,306
£2,306
£329 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 £1,502
£1,502
£215 per night
includes taxes & fees
Image gallery for ✨Remodeled Luxury Home with Pool – Steps to Clubhouse! 🏰 NEW Harry Potter Room!✨
1010 out of 10 rating
Exceptional
(72 reviews)
✨Remodeled Luxury Home with Pool – Steps to Clubhouse! 🏰 NEW Harry Potter Room!✨
Kissimmee, FL
9% off
Price is £1,134
£1,134
£162 per night
includes taxes & fees
Image gallery for Large Two Story Home with TWO Master Bedrooms with attached full baths.
1010 out of 10 rating
Exceptional
(55 reviews)
Large Two Story Home with TWO Master Bedrooms with attached full baths.
Kissimmee, FL
7% off
Price is £1,809
£1,809
£258 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 £1,635
£1,635
£234 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 £1,095
£1,095
£156 per night
includes taxes & fees
Image gallery for Where Jolly Delight and Magical Memories Unite
1010 out of 10 rating
Exceptional
(106 reviews)
Where Jolly Delight and Magical Memories Unite
Kissimmee, FL
7% off
Price is £1,979
£1,979
£283 per night
includes taxes & fees
Image gallery for FREE: Waterpark, South facing pool, Game room, Themed rooms, 2 Miles to Disney.
9.69.6 out of 10 rating
Exceptional
(137 reviews)
FREE: Waterpark, South facing pool, Game room, Themed rooms, 2 Miles to Disney.
Kissimmee, FL
8% off
Price is £1,512
£1,512
£216 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 £1,093
£1,093
£156 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 £1,134
£1,134
£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 £2,092
£2,092
£299 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 £2,085
£2,085
£298 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 £1,124
£1,124
£161 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 £1,767
£1,767
£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 £1,724
£1,724
£246 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 £1,301
£1,301
£186 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 £819
£819
£117 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 £994
£994
£142 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 £1,580
£1,580
£226 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Windsor Hills Resort
Showing deals for: 9 Sept - 12 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 £445
£445
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 £851
£851
for 3 nights, 1 villa
£284 per night
includes taxes & fees
*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)
The current price is £598
£598
for 3 nights, 1 home
£199 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 £480
£480
for 3 nights, 1 home
£160 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
44 reviews(44 reviews)
The current price is £856
£856
for 3 nights, 1 home
£285 per night
includes taxes & fees
Welcome To Magnolia Blossom Villa! South Facing Pool in Prime Location.
Sleeps 14 · 6 bedrooms · 4 bathrooms
9.89.8 out of 10
Exceptionalexceptional
50 reviews(50 reviews)
The current price is £756
£756
for 3 nights, 1 villa
£252 per night
includes taxes & fees
Top rated rentals - Windsor Hills Resort
Mr David Hillson
1010 out of 10
Exceptionalexceptional
106 reviews(106 reviews)
Lovely holiday home
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Charles Funhouse and Games Orlando
1010 out of 10
Exceptionalexceptional
15 reviews(15 reviews)
The Perfect Place to Stay
1010 out of 10
Exceptionalexceptional
107 reviews(107 reviews)
Great location
1010 out of 10
Exceptionalexceptional
105 reviews(105 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)
Brilliant location , wonderful attention to detail
1010 out of 10
Exceptionalexceptional
39 reviews(39 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