Windsor Hills Resort holiday rentals
We found 1,214 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor Hills Resort
Showing deals for:30 Jan - 6 Feb
Image gallery for Mickey's Pool House- Minutes away from Disney World
1010 out of 10, Exceptional, (16 reviews)
Exceptional
(16 reviews)
Mickey's Pool House- Minutes away from Disney World
Kissimmee, FL
8% off
Price is S$3,311
S$3,311
for 7 nights, 1 villa
S$473 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, Exceptional, (14 reviews)
Exceptional
(14 reviews)
Luxury 6 bedroom 4 bathroom pool villa in the world renowned Windsor Hills
Kissimmee, FL
7% off
Price is S$3,347
S$3,347
for 7 nights, 1 villa
S$478 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, Exceptional, (23 reviews)
Exceptional
(23 reviews)
Windsor Hills Resort! 6 Bedroom House, 2 miles to Disney, Private Pool & Spa🏝
Kissimmee, FL
7% off
Price is S$3,469
S$3,469
for 7 nights, 1 home
S$496 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, Exceptional, (44 reviews)
Exceptional
(44 reviews)
5% & 10% Discounts 2 King Ensuite on First Floor with Very Private Pool 5BD/5BA
Kissimmee, FL
6% off
Price is S$3,186
S$3,186
for 7 nights, 1 villa
S$455 per night
includes taxes & fees
Image gallery for South Facing Lux 5bd/5ba Pool Home W/spa & Private View 2mi To Disney!
9.29.2 out of 10, Wonderful, (24 reviews)
Wonderful
(24 reviews)
South Facing Lux 5bd/5ba Pool Home W/spa & Private View 2mi To Disney!
Kissimmee, FL
7% off
Price is S$2,844
S$2,844
for 7 nights, 1 villa
S$406 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, Exceptional, (46 reviews)
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$3,616
S$3,616
for 7 nights, 1 home
S$517 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, Exceptional, (128 reviews)
Exceptional
(128 reviews)
FREE Pool Heat - Stay in the BEST Luxury 5 bedroom villa with SOUTH facing pool
Kissimmee, FL
8% off
Price is S$3,350
S$3,350
for 7 nights, 1 villa
S$479 per night
includes taxes & fees
Image gallery for Large Two Story Home with TWO Master Bedrooms with attached full baths.
1010 out of 10, Exceptional, (58 reviews)
Exceptional
(58 reviews)
Large Two Story Home with TWO Master Bedrooms with attached full baths.
Kissimmee, FL
7% off
Price is S$3,097
S$3,097
for 7 nights, 1 home
S$442 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, Exceptional, (75 reviews)
Exceptional
(75 reviews)
6BR/4B Windsor Hills Villa, Pool & Game Room, 2 Miles from Walt Disney World
Kissimmee, FL
8% off
Price is S$3,726
S$3,726
for 7 nights, 1 home
S$532 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, Exceptional, (72 reviews)
Exceptional
(72 reviews)
😎RELAX at Windsor Hills🌴, minutes to Disney - 5 bed / 5 bath, Private Pool🌞
Kissimmee, FL
8% off
Price is S$3,097
S$3,097
for 7 nights, 1 home
S$442 per night
includes taxes & fees
Image gallery for Happy Thoughts Windsor Hills Resort 6BR Villa Private Heated Pool Spa Gameroom
9.49.4 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)
Happy Thoughts Windsor Hills Resort 6BR Villa Private Heated Pool Spa Gameroom
Kissimmee, FL
7% off
Price is S$3,596
S$3,596
for 7 nights, 1 home
S$514 per night
includes taxes & fees
Image gallery for Luxury 5BR Villa Near Disney w/ Pool & Game Room
1010 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
Luxury 5BR Villa Near Disney w/ Pool & Game Room
Kissimmee, FL
8% off
Price is S$2,951
S$2,951
for 7 nights, 1 villa
S$422 per night
includes taxes & fees
Image gallery for South facing pool with no rear neighbors! Free bbq grill and pool & spa heat.
1010 out of 10, Exceptional, (64 reviews)
Exceptional
(64 reviews)
South facing pool with no rear neighbors! Free bbq grill and pool & spa heat.
Kissimmee, FL
7% off
Price is S$3,443
S$3,443
for 7 nights, 1 home
S$492 per night
includes taxes & fees
Image gallery for Amazing 6-bedroom Villa with Private Pool Minutes from Disney! 5 Star Theming!
1010 out of 10, Exceptional, (44 reviews)
Exceptional
(44 reviews)
Amazing 6-bedroom Villa with Private Pool Minutes from Disney! 5 Star Theming!
Kissimmee, FL
8% off
Price is S$3,753
S$3,753
for 7 nights, 1 home
S$536 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, Exceptional, (112 reviews)
Exceptional
(112 reviews)
5-star family home with water park, private pool/hot tub- 2 stoplights to Disney
Kissimmee, FL
8% off
Price is S$3,309
S$3,309
for 7 nights, 1 home
S$473 per night
includes taxes & fees
Image gallery for Star Wars and Harry Potter Themed Lakeview Pool Home with Spa Near Disney World
8.28.2 out of 10, Very good, (20 reviews)
Very good
(20 reviews)
Star Wars and Harry Potter Themed Lakeview Pool Home with Spa Near Disney World
Kissimmee, FL
7% off
Price is S$2,906
S$2,906
for 7 nights, 1 villa
S$415 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, Exceptional, (85 reviews)
Exceptional
(85 reviews)
6 Bedroom Vacation Home with South Facing Pool in Windsor Hills close to Disney
Kissimmee, FL
8% off
Price is S$3,717
S$3,717
for 7 nights, 1 home
S$531 per night
includes taxes & fees
Image gallery for Ultimate Adventure Villa Top Rated 5 Star Disney more
1010 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
Ultimate Adventure Villa Top Rated 5 Star Disney more
Kissimmee, FL
8% off
Price is S$3,467
S$3,467
for 7 nights, 1 home
S$495 per night
includes taxes & fees
Image gallery for Disney South facing Pool Home, 5 minutes from Disney, Complimentary pool Heat!
1010 out of 10, Exceptional, (159 reviews)
Exceptional
(159 reviews)
Disney South facing Pool Home, 5 minutes from Disney, Complimentary pool Heat!
Kissimmee, FL
8% off
Price is S$3,017
S$3,017
for 7 nights, 1 home
S$431 per night
includes taxes & fees
Image gallery for Frozen and Star Wars Themed Villa with Pool and Game Room Near Disney Parks
8.88.8 out of 10, Excellent, (18 reviews)
Excellent
(18 reviews)
Frozen and Star Wars Themed Villa with Pool and Game Room Near Disney Parks
Kissimmee, FL
7% off
Price is S$2,881
S$2,881
for 7 nights, 1 villa
S$412 per night
includes taxes & fees
Image gallery for Modern Themed home 10mins from Disney with Pool, Resort, Game room and Free BBQ
1010 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)
Modern Themed home 10mins from Disney with Pool, Resort, Game room and Free BBQ
Kissimmee, FL
7% off
Price is S$4,011
S$4,011
for 7 nights, 1 home
S$573 per night
includes taxes & fees
Image gallery for Getaway with Mickey in Windsor Hills!
9.89.8 out of 10, Exceptional, (147 reviews)
Exceptional
(147 reviews)
Getaway with Mickey in Windsor Hills!
Kissimmee, FL
7% off
Price is S$1,637
S$1,637
for 7 nights, 1 apartment
S$234 per night
includes taxes & fees
Image gallery for NEW,Luxury,ThemeParks,5B&BA,Pool,Theater,Arcades,Mario Theme
1010 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)
NEW,Luxury,ThemeParks,5B&BA,Pool,Theater,Arcades,Mario Theme
Kissimmee, FL
7% off
Price is S$3,846
S$3,846
for 7 nights, 1 home
S$549 per night
includes taxes & fees
Image gallery for Where Jolly Delight and Magical Memories Unite
1010 out of 10, Exceptional, (110 reviews)
Exceptional
(110 reviews)
Where Jolly Delight and Magical Memories Unite
Kissimmee, FL
7% off
Price is S$3,647
S$3,647
for 7 nights, 1 home
S$521 per night
includes taxes & fees
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Find the best place to stay - Windsor Hills Resort
FREE Pool Heat - 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
128 reviews(128 reviews)
Relaxing 6BDR Villa just 15 mins from Disney w/ a Private Pool & Clubhouse!
Sleeps 12 · 6 bedrooms · 3+ bathrooms
6.06.0 out of 10
1 review(1 review)
*NEW* Windsor Hills - Ohana Oasis Pool Home Near Disney 4bd/4ba
Sleeps 9 · 4 bedrooms · 4 bathrooms
9.69.6 out of 10
Exceptionalexceptional
20 reviews(20 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
243 reviews(243 reviews)
Our DisneyDreamVilla - minutes to DisneyWorld!!!
Sleeps 11 · 5 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
242 reviews(242 reviews)
South facing pool with no rear neighbors! Free bbq grill and pool & spa heat.
Sleeps 12 · 6 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
64 reviews(64 reviews)