Windsor Hills Resort holiday homes
We found 1,220 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor Hills Resort
Showing deals for:12 Dec - 19 Dec
Image gallery for Villa 7757 - 3 mi from Disney, Free Heated Pool/Spa, BBQ, Game/Theater Rm, & PS5
9.89.8 out of 10 rating
Exceptional
(102 reviews)
Villa 7757 - 3 mi from Disney, Free Heated Pool/Spa, BBQ, Game/Theater Rm, & PS5
Kissimmee, FL
7% off
Price is NZ$4,672
NZ$4,672
for 7 nights, 1 home
NZ$667 per night
includes taxes & fees
Image gallery for 2025 Big Summer Blowout! Windsor Hills! 1st Floor-Waterpark! Close to Disney!
1010 out of 10 rating
Exceptional
(16 reviews)
2025 Big Summer Blowout! Windsor Hills! 1st Floor-Waterpark! Close to Disney!
Kissimmee, FL
7% off
Price is NZ$2,691
NZ$2,691
for 7 nights, 1 apartment
NZ$384 per night
includes taxes & fees
Image gallery for 6 Bed - 4 Bath Villa SOUTH FACING POOL - 2 Miles From DISNEY - OVER 100 Reviews
9.89.8 out of 10 rating
Exceptional
(128 reviews)
6 Bed - 4 Bath Villa SOUTH FACING POOL - 2 Miles From DISNEY - OVER 100 Reviews
Kissimmee, FL
7% off
Price is NZ$3,888
NZ$3,888
for 7 nights, 1 villa
NZ$555 per night
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
7% off
Price is NZ$4,841
NZ$4,841
for 7 nights, 1 villa
NZ$692 per night
includes taxes & fees
Image gallery for South Pool/Spa - free pool heat - no rear neighbors- 2 miles to Disney
9.89.8 out of 10 rating
Exceptional
(24 reviews)
South Pool/Spa - free pool heat - no rear neighbors- 2 miles to Disney
Kissimmee, FL
7% off
Price is NZ$7,007
NZ$7,007
for 7 nights, 1 villa
NZ$1,001 per night
includes taxes & fees
Image gallery for FREE Pool Heat - Stay in the BEST Luxury 5 bedroom villa with SOUTH facing pool
9.89.8 out of 10 rating
Exceptional
(126 reviews)
FREE Pool Heat - Stay in the BEST Luxury 5 bedroom villa with SOUTH facing pool
Kissimmee, FL
8% off
Price is NZ$3,380
NZ$3,380
for 7 nights, 1 villa
NZ$483 per night
includes taxes & fees
Image gallery for Luxury 6 bedroom 4 bathroom pool villa in the world renowned Windsor Hills
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Luxury 6 bedroom 4 bathroom pool villa in the world renowned Windsor Hills
Kissimmee, FL
7% off
Price is NZ$4,325
NZ$4,325
for 7 nights, 1 villa
NZ$618 per night
includes taxes & fees
Image gallery for Our DisneyDreamVilla - minutes to DisneyWorld!!!
1010 out of 10 rating
Exceptional
(241 reviews)
Our DisneyDreamVilla - minutes to DisneyWorld!!!
Kissimmee, FL
6% off
Price is NZ$3,518
NZ$3,518
for 7 nights, 1 villa
NZ$503 per night
includes taxes & fees
Image gallery for Villa 2655 - 3 mi from Disney, Free Heated Pool/Spa, BBQ, Game/Theater Rm, & PS5
9.69.6 out of 10 rating
Exceptional
(60 reviews)
Villa 2655 - 3 mi from Disney, Free Heated Pool/Spa, BBQ, Game/Theater Rm, & PS5
Kissimmee, FL
7% off
Price is NZ$4,435
NZ$4,435
for 7 nights, 1 home
NZ$634 per night
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 NZ$5,236
NZ$5,236
for 7 nights, 1 home
NZ$748 per night
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 NZ$4,672
NZ$4,672
for 7 nights, 1 home
NZ$667 per night
includes taxes & fees
Image gallery for Amazing Private Theater and Game Room! Pool/Spa & Star Wars room!
1010 out of 10 rating
Exceptional
(123 reviews)
Amazing Private Theater and Game Room! Pool/Spa & Star Wars room!
Kissimmee, FL
7% off
Price is NZ$4,052
NZ$4,052
for 7 nights, 1 home
NZ$579 per night
includes taxes & fees
Image gallery for 🏰 Magical 6-Bed Family Villa ✨[FREE Heated Pool, Spa & BBQ] 5 Mins to Disney 🎢
9.89.8 out of 10 rating
Exceptional
(180 reviews)
🏰 Magical 6-Bed Family Villa ✨[FREE Heated Pool, Spa & BBQ] 5 Mins to Disney 🎢
Kissimmee, FL
7% off
Price is NZ$3,510
NZ$3,510
for 7 nights, 1 home
NZ$501 per night
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 NZ$4,833
NZ$4,833
for 7 nights, 1 home
NZ$690 per night
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
(75 reviews)
6BR/4B Windsor Hills Villa, Pool & Game Room, 2 Miles from Walt Disney World
Kissimmee, FL
8% off
Price is NZ$4,813
NZ$4,813
for 7 nights, 1 home
NZ$688 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
(105 reviews)
Steps from clubhouse. "Be Our Guest" in Windsor Hills-Pool Heat
Kissimmee, FL
7% off
Price is NZ$3,081
NZ$3,081
for 7 nights, 1 home
NZ$440 per night
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
8% off
Price is NZ$6,211
NZ$6,211
for 7 nights, 1 home
NZ$887 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
(120 reviews)
RATED#1 BEST HOME Near Disney! LUXURY 5BEDROOM 5Bath VILLA ,GATED RESORT ,POOL
Kissimmee, FL
7% off
Price is NZ$4,849
NZ$4,849
for 7 nights, 1 villa
NZ$693 per night
includes taxes & fees
Image gallery for Newly Upgraded Disney Themed Vacation Retreat
9.89.8 out of 10 rating
Exceptional
(17 reviews)
Newly Upgraded Disney Themed Vacation Retreat
Kissimmee, FL
15% off
Price is NZ$3,073
NZ$3,073
for 7 nights, 1 villa
NZ$439 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
(38 reviews)
Star Wars Themed BR Free Resort Waterpark and Pool Heat 2.5 miles to Disney
Kissimmee, FL
8% off
Price is NZ$3,840
NZ$3,840
for 7 nights, 1 home
NZ$549 per night
includes taxes & fees
Image gallery for Villa 2619 - 3 mi from Disney, Free Heated Pool/Spa, BBQ, Game/Theater Rm, & PS5
1010 out of 10 rating
Exceptional
(83 reviews)
Villa 2619 - 3 mi from Disney, Free Heated Pool/Spa, BBQ, Game/Theater Rm, & PS5
Kissimmee, FL
7% off
Price is NZ$3,807
NZ$3,807
for 7 nights, 1 home
NZ$544 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
(63 reviews)
Sun filled south facing pool & spa with no rear neighbors! Game room!
Kissimmee, FL
7% off
Price is NZ$3,631
NZ$3,631
for 7 nights, 1 home
NZ$519 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, FL
8% off
Price is NZ$4,835
NZ$4,835
for 7 nights, 1 home
NZ$691 per night
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
(7 reviews)
TOP-RATED Windsor Hills Home ♥ THEATER ROOM, Game Room, Pool/Spa ♥4 Mi to Disney
Kissimmee, FL
7% off
Price is NZ$3,974
NZ$3,974
for 7 nights, 1 home
NZ$568 per night
includes taxes & fees
Find spaces that suit your style
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)
😎RELAX at Windsor Hills🌴, minutes to Disney - 5 bed / 5 bath, Private Pool🌞
Sleeps 10 · 5 bedrooms · 5 bathrooms
9.89.8 out of 10
Exceptionalexceptional
70 reviews(70 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
200 reviews(200 reviews)
🌟NO CARPETS - ONE LEVEL🌟Newly Renovated Pool/Theater Home In Windsor Hills
Sleeps 8 · 4 bedrooms · 4 bathrooms
9.89.8 out of 10
Exceptionalexceptional
138 reviews(138 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