Windsor Hills Resort holiday rentals
We found 1,195 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor Hills Resort
Showing deals for:5 Dec - 12 Dec
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
8% off
Price is S$3,286
S$3,286
for 7 nights, 1 villa
S$469 nightly
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
8% off
Price is S$3,840
S$3,840
for 7 nights, 1 home
S$549 nightly
Includes taxes & fees
Image gallery for AWESOME 6BR/4BA Resort Private Pool/Spa - 2 mi to Disney - Game Room/Theme Rooms
9.89.8 out of 10 rating
Exceptional
(46 reviews)
AWESOME 6BR/4BA Resort Private Pool/Spa - 2 mi to Disney - Game Room/Theme Rooms
Kissimmee, FL
8% off
Price is S$3,589
S$3,589
for 7 nights, 1 home
S$513 nightly
Includes taxes & fees
Image gallery for Elegantly Upgraded 4 bedroom Windsor Hills home with COMPLIMENTARY POOL HEAT!
9.69.6 out of 10 rating
Exceptional
(80 reviews)
Elegantly Upgraded 4 bedroom Windsor Hills home with COMPLIMENTARY POOL HEAT!
Kissimmee, FL
7% off
Price is S$2,785
S$2,785
for 7 nights, 1 home
S$398 nightly
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
(38 reviews)
Enchanting Retreat: A Charming 6-Bd Oasis with Themed Rooms and Pv Pool Bliss
Kissimmee, FL
7% off
Price is S$2,754
S$2,754
for 7 nights, 1 home
S$393 nightly
Includes taxes & fees
Image gallery for Stay in the BEST Luxury 5 bedroom villa with SOUTH facing pool
9.89.8 out of 10 rating
Exceptional
(126 reviews)
Stay in the BEST Luxury 5 bedroom villa with SOUTH facing pool
Kissimmee, FL
8% off
Price is S$2,596
S$2,596
for 7 nights, 1 villa
S$371 nightly
Includes taxes & fees
Image gallery for 5% & 10% Discounts 2 King Ensuite on First Floor with Very Private Pool 5BD/5BA
9.89.8 out of 10 rating
Exceptional
(42 reviews)
5% & 10% Discounts 2 King Ensuite on First Floor with Very Private Pool 5BD/5BA
Kissimmee, FL
6% off
Price is S$3,149
S$3,149
for 7 nights, 1 villa
S$450 nightly
Includes taxes & fees
Image gallery for Villa Sonrisa - 5 Bedroom/5 Bath Luxury, Minutes To Disney In Windsor Hills
1010 out of 10 rating
Exceptional
(219 reviews)
Villa Sonrisa - 5 Bedroom/5 Bath Luxury, Minutes To Disney In Windsor Hills
Kissimmee, FL
7% off
Price is S$3,200
S$3,200
for 7 nights, 1 home
S$457 nightly
Includes taxes & fees
Image gallery for 6BR/4B Windsor Hills Villa, Pool & Game Room, 2 Miles from Walt Disney World
9.89.8 out of 10 rating
Exceptional
(74 reviews)
6BR/4B Windsor Hills Villa, Pool & Game Room, 2 Miles from Walt Disney World
Kissimmee, FL
8% off
Price is S$3,698
S$3,698
for 7 nights, 1 home
S$528 nightly
Includes taxes & fees
Image gallery for Windsor Hills Resort! 6 Bedroom House, 2 miles to Disney, Private Pool & Spa🏝
1010 out of 10 rating
Exceptional
(23 reviews)
Windsor Hills Resort! 6 Bedroom House, 2 miles to Disney, Private Pool & Spa🏝
Kissimmee, FL
7% off
Price is S$4,025
S$4,025
for 7 nights, 1 home
S$575 nightly
Includes taxes & fees
Image gallery for 5-star family home with water park, private pool/hot tub- 2 stoplights to Disney
9.89.8 out of 10 rating
Exceptional
(111 reviews)
5-star family home with water park, private pool/hot tub- 2 stoplights to Disney
Kissimmee, FL
8% off
Price is S$3,284
S$3,284
for 7 nights, 1 home
S$469 nightly
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
(96 reviews)
Free Pool Heat and BBQ! No Rear Neighbors! South Facing Pool!-AC Game Room!
Kissimmee, FL
8% off
Price is S$3,476
S$3,476
for 7 nights, 1 home
S$497 nightly
Includes taxes & fees
Image gallery for Large Two Story Home with TWO Master Bedrooms with attached full baths.
1010 out of 10 rating
Exceptional
(57 reviews)
Large Two Story Home with TWO Master Bedrooms with attached full baths.
Kissimmee, FL
7% off
Price is S$3,073
S$3,073
for 7 nights, 1 home
S$439 nightly
Includes taxes & fees
Image gallery for Upscale WINDSOR HILLS Private Home ♥ Pool/Spa, GAME ROOM ♥ 4 mi to DISNEY WORLD
9.89.8 out of 10 rating
Exceptional
(49 reviews)
Upscale WINDSOR HILLS Private Home ♥ Pool/Spa, GAME ROOM ♥ 4 mi to DISNEY WORLD
Kissimmee, FL
7% off
Price is S$2,974
S$2,974
for 7 nights, 1 home
S$425 nightly
Includes taxes & fees
Image gallery for Water Park & Fantastic Pool only Minutes To Walt Disney World's Front Gate!!!
9.89.8 out of 10 rating
Exceptional
(214 reviews)
Water Park & Fantastic Pool only Minutes To Walt Disney World's Front Gate!!!
Kissimmee, FL
7% off
Price is S$1,871
S$1,871
for 7 nights, 1 apartment
S$267 nightly
Includes taxes & fees
Image gallery for Superhero Mickey Resort Townhome next to Disney World
9.89.8 out of 10 rating
Exceptional
(12 reviews)
Superhero Mickey Resort Townhome next to Disney World
Kissimmee, FL
7% off
Price is S$1,754
S$1,754
for 7 nights, 1 home
S$251 nightly
Includes taxes & fees
Image gallery for Steps from clubhouse. "Be Our Guest" in Windsor Hills-Pool Heat
1010 out of 10 rating
Exceptional
(105 reviews)
Steps from clubhouse. "Be Our Guest" in Windsor Hills-Pool Heat
Kissimmee, FL
7% off
Price is S$1,767
S$1,767
for 7 nights, 1 home
S$252 nightly
Includes taxes & fees
Image gallery for NEW,Luxury,ThemeParks,5B&BA,Pool,Theater,Arcades,Mario Theme
1010 out of 10 rating
Exceptional
(11 reviews)
NEW,Luxury,ThemeParks,5B&BA,Pool,Theater,Arcades,Mario Theme
Kissimmee, FL
7% off
Price is S$3,998
S$3,998
for 7 nights, 1 home
S$571 nightly
Includes taxes & fees
Image gallery for ✨LUXURIOUS REMODEL wPOOL✨FREE Waterpark
1010 out of 10 rating
Exceptional
(76 reviews)
✨LUXURIOUS REMODEL wPOOL✨FREE Waterpark
Kissimmee, FL
7% off
Price is S$2,345
S$2,345
for 7 nights, 1 home
S$335 nightly
Includes taxes & fees
Image gallery for 5 Stars Resort, 2 Miles To Disney, 3 BD, 3 BA, Private Pool, Free Wifi
9.69.6 out of 10 rating
Exceptional
(131 reviews)
5 Stars Resort, 2 Miles To Disney, 3 BD, 3 BA, Private Pool, Free Wifi
Kissimmee, FL
7% off
Price is S$1,565
S$1,565
for 7 nights, 1 home
S$224 nightly
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, FL
8% off
Price is S$3,313
S$3,313
for 7 nights, 1 home
S$473 nightly
Includes taxes & fees
Image gallery for TOP-RATED Windsor Hills Home ♥ THEATER ROOM, Game Room, Pool/Spa ♥4 Mi to Disney
1010 out of 10 rating
Exceptional
(5 reviews)
TOP-RATED Windsor Hills Home ♥ THEATER ROOM, Game Room, Pool/Spa ♥4 Mi to Disney
Kissimmee, FL
7% off
Price is S$3,053
S$3,053
for 7 nights, 1 home
S$436 nightly
Includes taxes & fees
Image gallery for High End Disney Condo, Better Known As The Animal Kingdom...
9.89.8 out of 10 rating
Exceptional
(53 reviews)
High End Disney Condo, Better Known As The Animal Kingdom...
Kissimmee, FL
7% off
Price is S$1,803
S$1,803
for 7 nights, 1 apartment
S$258 nightly
Includes taxes & fees
Image gallery for Getaway with Mickey in Windsor Hills!
9.89.8 out of 10 rating
Exceptional
(147 reviews)
Getaway with Mickey in Windsor Hills!
Kissimmee, FL
7% off
Price is S$1,625
S$1,625
for 7 nights, 1 apartment
S$232 nightly
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
97 reviews(97 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)
*NEW* Windsor Hills - Ohana Oasis Pool Home Near Disney 4bd/4ba
Sleeps 9 · 4 bedrooms · 4 bathrooms
9.69.6 out of 10
Exceptionalexceptional
19 reviews(19 reviews)
6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ
Sleeps 14 · 6 bedrooms · 4 bathrooms
9.49.4 out of 10
Exceptionalexceptional
240 reviews(240 reviews)
Villa The Dreamers , ultra modern villa , 3 miles from Disney , pool
Sleeps 10 · 5 bedrooms · 5 bathrooms
9.69.6 out of 10
Exceptionalexceptional
199 reviews(199 reviews)
Stay in the BEST Luxury 5 bedroom villa with SOUTH facing pool
Sleeps 10 · 5 bedrooms · 5 bathrooms
9.89.8 out of 10
Exceptionalexceptional
126 reviews(126 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, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value