Windsor Hills Resort holiday rentals
We found 1,220 holiday rentals — enter your dates for availability
Holiday rentals with weekly discounts - Windsor Hills Resort
Showing deals for:27 Feb - 6 Mar
Image gallery for Weekly discount 10-20% OFF 5 STAR Disney Adventure Villa @ Windsor Hills Resort
9.89.8 out of 10, Exceptional, (228 reviews)
Exceptional
(228 reviews)
Weekly discount 10-20% OFF 5 STAR Disney Adventure Villa @ Windsor Hills Resort
Kissimmee, FL
7% off
Price is S$3,808
S$3,808
for 7 nights, 1 home
S$544 per night
includes taxes & fees
Image gallery for Villa 7757 - 3 mi from Disney, Free Heated Pool/Spa, BBQ, Game/Theater Rm, & PS5
9.89.8 out of 10, Exceptional, (104 reviews)
Exceptional
(104 reviews)
Villa 7757 - 3 mi from Disney, Free Heated Pool/Spa, BBQ, Game/Theater Rm, & PS5
Kissimmee, FL
7% off
Price is S$3,998
S$3,998
for 7 nights, 1 home
S$571 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$3,720
S$3,720
for 7 nights, 1 villa
S$531 per night
includes taxes & fees
Image gallery for Windsor Hills Townhome | Across from Clubhouse | Mickey-Themed Room | Sleeps 6
9.89.8 out of 10, Exceptional, (69 reviews)
Exceptional
(69 reviews)
Windsor Hills Townhome | Across from Clubhouse | Mickey-Themed Room | Sleeps 6
Kissimmee, FL
23% off
Price is S$1,765
S$1,765
for 7 nights, 1 home
S$252 per night
includes taxes & fees
Image gallery for 5★ Disney-Themed Villa – Pool, Renovated, Free Resort Perks – 5 Min to Disney
1010 out of 10, Exceptional, (77 reviews)
Exceptional
(77 reviews)
5★ Disney-Themed Villa – Pool, Renovated, Free Resort Perks – 5 Min to Disney
Kissimmee, FL
8% off
Price is S$3,051
S$3,051
for 7 nights, 1 home
S$436 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
7% off
Price is S$4,406
S$4,406
for 7 nights, 1 villa
S$629 per night
includes taxes & fees
Image gallery for Disney Nearby! Updated Condo with Modern Appliances
9.69.6 out of 10, Exceptional, (52 reviews)
Exceptional
(52 reviews)
Disney Nearby! Updated Condo with Modern Appliances
Kissimmee, FL
13% off
Price is S$2,136
S$2,136
for 7 nights, 1 apartment
S$305 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$4,860
S$4,860
for 7 nights, 1 home
S$694 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, (129 reviews)
Exceptional
(129 reviews)
FREE Pool Heat - Stay in the BEST Luxury 5 bedroom villa with SOUTH facing pool
Kissimmee, FL
8% off
Price is S$3,588
S$3,588
for 7 nights, 1 villa
S$513 per night
includes taxes & fees
Image gallery for Disney Escape | Renovated Windsor Hills Condo w/ Balcony & Themed Bedrooms
9.89.8 out of 10, Exceptional, (22 reviews)
Exceptional
(22 reviews)
Disney Escape | Renovated Windsor Hills Condo w/ Balcony & Themed Bedrooms
Kissimmee, FL
15% off
Price is S$2,941
S$2,941
for 7 nights, 1 apartment
S$420 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$3,506
S$3,506
for 7 nights, 1 home
S$501 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$4,474
S$4,474
for 7 nights, 1 home
S$639 per night
includes taxes & fees
Image gallery for Family Paradise w/ Pvt Pool, BBQ Grill, Themed Bedrooms, Game Room & Club access
9.29.2 out of 10, Wonderful, (9 reviews)
Wonderful
(9 reviews)
Family Paradise w/ Pvt Pool, BBQ Grill, Themed Bedrooms, Game Room & Club access
Kissimmee, FL
7% off
Price is S$4,281
S$4,281
for 7 nights, 1 home
S$612 per night
includes taxes & fees
Image gallery for 6-Bedroom Luxury Villa in Windsor Hills South Facing Pool 3 miles to Disney
9.69.6 out of 10, Exceptional, (154 reviews)
Exceptional
(154 reviews)
6-Bedroom Luxury Villa in Windsor Hills South Facing Pool 3 miles to Disney
Kissimmee, FL
7% off
Price is S$3,559
S$3,559
for 7 nights, 1 home
S$508 per night
includes taxes & fees
Image gallery for Theme Parks, Heated Pool, Theater, Arcades, Mario Kart Bedroom
1010 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)
Theme Parks, Heated Pool, Theater, Arcades, Mario Kart Bedroom
Kissimmee, FL
7% off
Price is S$5,280
S$5,280
for 7 nights, 1 home
S$754 per night
includes taxes & fees
Image gallery for 8 Mins To Disney W/Poolside Theater, South Facing Pool, Game Room And Waterpark
9.89.8 out of 10, Exceptional, (44 reviews)
Exceptional
(44 reviews)
8 Mins To Disney W/Poolside Theater, South Facing Pool, Game Room And Waterpark
Kissimmee, FL
7% off
Price is S$5,185
S$5,185
for 7 nights, 1 home
S$741 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, Wonderful, (14 reviews)
Wonderful
(14 reviews)
Magical Adv 5 Star Villa Movie Room Arcade Pool and More
Kissimmee, FL
7% off
Price is S$4,427
S$4,427
for 7 nights, 1 home
S$632 per night
includes taxes & fees
Image gallery for Star Wars & Harry Potter-Themed Lakeview Pool Home Near Disney
8.28.2 out of 10, Very good, (20 reviews)
Very good
(20 reviews)
Star Wars & Harry Potter-Themed Lakeview Pool Home Near Disney
Kissimmee, FL
7% off
Price is S$4,037
S$4,037
for 7 nights, 1 villa
S$577 per night
includes taxes & fees
Image gallery for Villa Sonrisa - 5 Bedroom/5 Bath Luxury, Minutes To Disney In Windsor Hills
1010 out of 10, Exceptional, (221 reviews)
Exceptional
(221 reviews)
Villa Sonrisa - 5 Bedroom/5 Bath Luxury, Minutes To Disney In Windsor Hills
Kissimmee, FL
7% off
Price is S$2,832
S$2,832
for 7 nights, 1 home
S$405 per night
includes taxes & fees
Image gallery for Jedi Training Camp Top Rated 5 Star Villa
9.89.8 out of 10, Exceptional, (81 reviews)
Exceptional
(81 reviews)
Jedi Training Camp Top Rated 5 Star Villa
Kissimmee, FL
8% off
Price is S$4,667
S$4,667
for 7 nights, 1 home
S$667 per night
includes taxes & fees
Image gallery for Frozen & Star Wars-Themed Villa with Private Pool Near Disney
8.08.0 out of 10, Very good, (19 reviews)
Very good
(19 reviews)
Frozen & Star Wars-Themed Villa with Private Pool Near Disney
Kissimmee, FL
7% off
Price is S$3,417
S$3,417
for 7 nights, 1 home
S$488 per night
includes taxes & fees
Image gallery for Ohana House: 5 Min to WDW! | 100% Renovated | Modern, Luxury, Lakeview, Gameroom
1010 out of 10, Exceptional, (139 reviews)
Exceptional
(139 reviews)
Ohana House: 5 Min to WDW! | 100% Renovated | Modern, Luxury, Lakeview, Gameroom
Kissimmee, FL
11% off
Price is S$4,601
S$4,601
for 7 nights, 1 home
S$657 per night
includes taxes & fees
Image gallery for Windsor Hills Resort- Free Heated Pool. 5 bedrooms plus an office with 3.5 bath
8.88.8 out of 10, Excellent, (86 reviews)
Excellent
(86 reviews)
Windsor Hills Resort- Free Heated Pool. 5 bedrooms plus an office with 3.5 bath
Kissimmee, FL
7% off
Price is S$2,963
S$2,963
for 7 nights, 1 home
S$423 per night
includes taxes & fees
Image gallery for Star Wars & Harry Potter Villa with Pool, Game Room Near Disney
8.88.8 out of 10, Excellent, (41 reviews)
Excellent
(41 reviews)
Star Wars & Harry Potter Villa with Pool, Game Room Near Disney
Kissimmee, FL
7% off
Price is S$3,657
S$3,657
for 7 nights, 1 home
S$522 per night
includes taxes & fees
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Find the best place to stay - Windsor Hills Resort
Showing deals for: 23 Feb - 26 Feb
Fun for kids and parents 6BR/4BA with private pool & hot tub in resort community
Sleeps 12 · 6 bedrooms · 4 bathrooms
9.69.6 out of 10
Exceptionalexceptional
70 reviews(70 reviews)
The current price is S$1,515
S$1,515
for 3 nights, 1 home
S$505 per night
includes taxes & fees
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)
The current price is S$1,620
S$1,620
for 3 nights, 1 villa
S$540 per night
includes taxes & fees
Vacation Rental near Disney, Univeral Studios, Epic, w/free parking and Wi-Fi.
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.29.2 out of 10
Wonderfulwonderful
220 reviews(220 reviews)
The current price is S$845
S$845
for 3 nights, 1 apartment
S$282 per night
includes taxes & fees
AWESOME 6BR/4BA Resort Private Pool/Spa - 2 mi to Disney - Game Room/Theme Rooms
Sleeps 12 · 6 bedrooms · 4 bathrooms
9.89.8 out of 10
Exceptionalexceptional
46 reviews(46 reviews)
The current price is S$1,762
S$1,762
for 3 nights, 1 home
S$587 per night
includes taxes & fees
Pandora's Paradise 3-bedroom townhome with water park and 10 minutes from Disney
Sleeps 6 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
70 reviews(70 reviews)
The current price is S$933
S$933
for 3 nights, 1 home
S$311 per night
includes taxes & fees