Windsor Hills holiday rentals
We found 2,860 holiday rentals — enter your dates for availability
Select from 1006 houses, 332 flats and other holiday rentals to find the perfect place for your stay in Windsor Hills. Whether you’re travelling with friends, family or just with your pet, holiday rentals have the amenities that you expect for your stay, such as air conditioning and Wi-Fi. You'll be able to choose a property to rent for everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Windsor Hills
Showing deals for:23 Jan - 30 Jan
Image gallery for 🏰 Magical 6-Bed Family Villa ✨[FREE Heated Pool, Spa & BBQ] 5 Mins to Disney 🎢
9.89.8 out of 10, Exceptional, (181 reviews)
Exceptional
(181 reviews)
🏰 Magical 6-Bed Family Villa ✨[FREE Heated Pool, Spa & BBQ] 5 Mins to Disney 🎢
Kissimmee, FL
7% off
Price is AU$3,614
AU$3,614
for 7 nights, 1 home
AU$516 per night
includes taxes & fees
Image gallery for Remodeled~ Themed~Arcade~Windsor Hills~2.5 Miles from Disney World Entrance
9.89.8 out of 10, Exceptional, (179 reviews)
Exceptional
(179 reviews)
Remodeled~ Themed~Arcade~Windsor Hills~2.5 Miles from Disney World Entrance
Kissimmee, FL
7% off
Price is AU$3,025
AU$3,025
for 7 nights, 1 apartment
AU$432 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, Exceptional, (24 reviews)
Exceptional
(24 reviews)
South Pool/Spa - free pool heat - no rear neighbors- 2 miles to Disney
Kissimmee, FL
7% off
Price is AU$6,382
AU$6,382
for 7 nights, 1 villa
AU$912 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 AU$3,997
AU$3,997
for 7 nights, 1 villa
AU$571 per night
includes taxes & fees
Image gallery for Our DisneyDreamVilla - minutes to DisneyWorld!!!
1010 out of 10, Exceptional, (242 reviews)
Exceptional
(242 reviews)
Our DisneyDreamVilla - minutes to DisneyWorld!!!
Kissimmee, FL
6% off
Price is AU$3,133
AU$3,133
for 7 nights, 1 villa
AU$448 per night
includes taxes & fees
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 AU$3,954
AU$3,954
for 7 nights, 1 villa
AU$565 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 AU$1,956
AU$1,956
for 7 nights, 1 apartment
AU$279 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 AU$4,080
AU$4,080
for 7 nights, 1 home
AU$583 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 AU$3,637
AU$3,637
for 7 nights, 1 home
AU$520 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 AU$3,634
AU$3,634
for 7 nights, 1 villa
AU$519 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
7% off
Price is AU$4,320
AU$4,320
for 7 nights, 1 home
AU$617 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 AU$3,396
AU$3,396
for 7 nights, 1 villa
AU$485 per night
includes taxes & fees
Image gallery for Windsor Hills - close to Disney, free heated pool, newly renovated bathroom
8.88.8 out of 10, Excellent, (84 reviews)
Excellent
(84 reviews)
Windsor Hills - close to Disney, free heated pool, newly renovated bathroom
Kissimmee, FL
7% off
Price is AU$3,480
AU$3,480
for 7 nights, 1 home
AU$497 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 AU$3,698
AU$3,698
for 7 nights, 1 home
AU$528 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 AU$4,451
AU$4,451
for 7 nights, 1 home
AU$636 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 AU$3,485
AU$3,485
for 7 nights, 1 villa
AU$498 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, (71 reviews)
Exceptional
(71 reviews)
😎RELAX at Windsor Hills🌴, minutes to Disney - 5 bed / 5 bath, Private Pool🌞
Kissimmee, FL
8% off
Price is AU$3,699
AU$3,699
for 7 nights, 1 home
AU$528 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
7% off
Price is AU$4,502
AU$4,502
for 7 nights, 1 home
AU$643 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 AU$3,950
AU$3,950
for 7 nights, 1 home
AU$564 per night
includes taxes & fees
Image gallery for Vacation Rental near Disney, Univeral Studios, Epic, w/free parking and Wi-Fi.
9.29.2 out of 10, Wonderful, (218 reviews)
Wonderful
(218 reviews)
Vacation Rental near Disney, Univeral Studios, Epic, w/free parking and Wi-Fi.
Kissimmee, FL
7% off
Price is AU$1,624
AU$1,624
for 7 nights, 1 apartment
AU$232 per night
includes taxes & fees
Image gallery for GREAT DEALS , STAR WARS, HARRY POTTER, MINIONS THEMED BEDROOMS
1010 out of 10, Exceptional, (51 reviews)
Exceptional
(51 reviews)
GREAT DEALS , STAR WARS, HARRY POTTER, MINIONS THEMED BEDROOMS
Kissimmee, FL
8% off
Price is AU$5,206
AU$5,206
for 7 nights, 1 home
AU$744 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 AU$3,270
AU$3,270
for 7 nights, 1 home
AU$467 per night
includes taxes & fees
Image gallery for Steps from Waterpark/Pool. Next to Disney w/ Frozen, Aladdin, Beauty&Beast theme
1010 out of 10, Exceptional, (223 reviews)
Exceptional
(223 reviews)
Steps from Waterpark/Pool. Next to Disney w/ Frozen, Aladdin, Beauty&Beast theme
Kissimmee, FL
7% off
Price is AU$2,532
AU$2,532
for 7 nights, 1 apartment
AU$362 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 AU$4,621
AU$4,621
for 7 nights, 1 home
AU$660 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Windsor Hills
Our DisneyDreamVilla - minutes to DisneyWorld!!!
Sleeps 11 · 5 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
242 reviews(242 reviews)
☆ Location matters! Private palm paradise view from pool - 1 block to waterpark
Sleeps 10 · 5 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
16 reviews(16 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)
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)
Family Friendly Windsor Hills 5BR/5BA Villa-SW Facing Pool, 2 mi. from Disney
Sleeps 11 · 5 bedrooms · 5 bathrooms
9.69.6 out of 10
Exceptionalexceptional
103 reviews(103 reviews)
TOP-RATED Windsor Hills Home ♥ THEATER ROOM, Game Room, Pool/Spa ♥4 Mi to Disney
Sleeps 10 · 5 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
8 reviews(8 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
Frequently asked questions
How much does it cost to rent a holiday home in Windsor Hills?
Season, property type and length of stay are some of the things that can affect the price of a holiday home. Simply add your travel dates to find your perfect escape. From homey country cottages to expansive villas, all Stayz holiday homes offer terrific value.
How much does it cost to rent a beach house in Windsor Hills?
When you travel and the style and size of the property will help determine the cost of your beachside holiday home. Put in your Windsor Hills travel dates to see your options on Stayz. Can't live without a private pool? Use our filters to select the amenities and features you want in your beach house.
What are the top attractions for families in Windsor Hills?
Keep your kids occupied at these fabulous family-friendly attractions in Windsor Hills:
- Surfari Water Park
- Northeast Regional Park
- Lake Davenport
How old do you have to be to rent a holiday home in Windsor Hills?
The minimum age requirements can differ across properties on Stayz, so check the rules of the holiday home in Windsor Hills you want to book. But typically, it's 16, 18 or 21.
How long can I rent a holiday home in Windsor Hills for?
The amount of time you can stay in a Windsor Hills holiday home for is down to the property. Just tap in your dates of travel to view options offering longer term stays. They feature everything you need to make your extended break more comfortable and enjoyable, like air conditioning and kitchens. Some Stayz holiday homes may also offer discounted weekly or monthly prices, so you can stay longer for less money.