Windsor Hills Resort holiday lettings
We found 1,206 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor Hills Resort
Showing deals for:22 Aug - 29 Aug
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 £1,930
£1,930
£276 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 £1,931
£1,931
£276 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 £1,719
£1,719
£246 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 £2,173
£2,173
£310 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 £1,908
£1,908
£273 per night
includes taxes & fees
Image gallery for Guardians Theater 5BR Home Resort w Pool Hot Tub
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Guardians Theater 5BR Home Resort w Pool Hot Tub
Kissimmee, FL
7% off
Price is £2,359
£2,359
£337 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 £1,838
£1,838
£263 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 £1,112
£1,112
£159 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 £1,381
£1,381
£197 per night
includes taxes & fees
Image gallery for *Great Privacy Backyard*6BR Luxury Villa Pool/Spa
8.08.0 out of 10 rating
Very good
(18 reviews)
*Great Privacy Backyard*6BR Luxury Villa Pool/Spa
Kissimmee, FL
7% off
Price is £1,630
£1,630
£233 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 £1,810
£1,810
£259 per night
includes taxes & fees
Image gallery for Paradise Villa 2.5 miles from Disney Gate
1010 out of 10 rating
Exceptional
(21 reviews)
Paradise Villa 2.5 miles from Disney Gate
Kissimmee, FL
7% off
Price is £2,044
£2,044
£292 per night
includes taxes & fees
Image gallery for NEW,Luxury,ThemeParks,5B&BA,Pool,Theater,Arcades,Mario Theme
1010 out of 10 rating
Exceptional
(9 reviews)
NEW,Luxury,ThemeParks,5B&BA,Pool,Theater,Arcades,Mario Theme
Kissimmee, FL
7% off
Price is £2,108
£2,108
£301 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 £1,011
£1,011
£144 per night
includes taxes & fees
Image gallery for Contemporary Disney Villa Minutes from Attractions
9.69.6 out of 10 rating
Exceptional
(20 reviews)
Contemporary Disney Villa Minutes from Attractions
Kissimmee, FL
7% off
Price is £1,787
£1,787
£255 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 £1,137
£1,137
£162 per night
includes taxes & fees
Image gallery for Windsor Hills Waterpark Community, NEW 2025 Game Room! Pool/Spa, Disney Rooms
1010 out of 10 rating
Exceptional
(8 reviews)
Windsor Hills Waterpark Community, NEW 2025 Game Room! Pool/Spa, Disney Rooms
Kissimmee, FL
5% off
Price is £1,745
£1,745
£249 per night
includes taxes & fees
Image gallery for Flexible Cancellation Policy-Upgraded 4-Bed/4 Bath, Pool/Spa 2 Miles to Disney
1010 out of 10 rating
Exceptional
(112 reviews)
Flexible Cancellation Policy-Upgraded 4-Bed/4 Bath, Pool/Spa 2 Miles to Disney
Kissimmee, FL
8% off
Price is £2,409
£2,409
£344 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 £1,731
£1,731
£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
(93 reviews)
Resort Style Living 2 miles from Disney World
Kissimmee, FL
7% off
Price is £878
£878
£125 per night
includes taxes & fees
Image gallery for New Luxury Townhome at Windsor Hills Resort 2 Miles from Disney
1010 out of 10 rating
Exceptional
(22 reviews)
New Luxury Townhome at Windsor Hills Resort 2 Miles from Disney
Kissimmee, FL
15% off
Price is £1,483
£1,483
£212 per night
includes taxes & fees
Image gallery for 😎RELAX at Windsor Hills🌴, minutes to Disney - 5 bed / 5 bath, Private Pool🌞
9.89.8 out of 10 rating
Exceptional
(65 reviews)
😎RELAX at Windsor Hills🌴, minutes to Disney - 5 bed / 5 bath, Private Pool🌞
Kissimmee, FL
7% off
Price is £1,889
£1,889
£270 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
(48 reviews)
Lake View and Top floor on Disney's doorstep - Great location
Kissimmee, FL
7% off
Price is £1,009
£1,009
£144 per night
includes taxes & fees
Image gallery for Mickey's Pool House- Minutes away from Disney World
1010 out of 10 rating
Exceptional
(16 reviews)
Mickey's Pool House- Minutes away from Disney World
Kissimmee, FL
7% off
Price is £1,963
£1,963
£280 per night
includes taxes & fees
Find spaces that suit your style
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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)
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)
*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)
Windsor Hills by Nova
6.06.0 out of 10
2 reviews(2 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)
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
101 reviews(101 reviews)
Top rated rentals - Windsor Hills Resort
Fabulous Villa
1010 out of 10
Exceptionalexceptional
63 reviews(63 reviews)
Sun all Day 5 star stay
1010 out of 10
Exceptionalexceptional
60 reviews(60 reviews)
We loved our stay here
1010 out of 10
Exceptionalexceptional
160 reviews(160 reviews)
Spacious, comfortable and well equipped house
1010 out of 10
Exceptionalexceptional
231 reviews(231 reviews)
Ten Out of Ten Stay
1010 out of 10
Exceptionalexceptional
66 reviews(66 reviews)
Great condo, super location, fully equipped
1010 out of 10
Exceptionalexceptional
160 reviews(160 reviews)
Summer 23
1010 out of 10
Exceptionalexceptional
157 reviews(157 reviews)
Great Location
1010 out of 10
Exceptionalexceptional
117 reviews(117 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