Windsor Hills holiday rentals
We found 2,794 holiday rentals — enter your dates for availability
Select from 977 houses, 323 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:3 Oct - 10 Oct
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 AU$3,885
AU$3,885
AU$555 per night
includes taxes & fees
Image gallery for Windsor Palms Villa w/South Facing Private Pool & Hot Tub Close to Disney & Golf
9.89.8 out of 10 rating
Exceptional
(94 reviews)
Windsor Palms Villa w/South Facing Private Pool & Hot Tub Close to Disney & Golf
Kissimmee, FL
7% off
Price is AU$2,343
AU$2,343
AU$335 per night
includes taxes & fees
Image gallery for 3 Miles from Disney!!!!! 4 Bedroom Villa with Private Pool/Game Room
9.89.8 out of 10 rating
Exceptional
(18 reviews)
3 Miles from Disney!!!!! 4 Bedroom Villa with Private Pool/Game Room
Kissimmee, FL
7% off
Price is AU$2,832
AU$2,832
AU$405 per night
includes taxes & fees
Image gallery for Welcome to The new Star, 5 bedrooms , 4 bathrooms southfacing pool and spa
9.29.2 out of 10 rating
Wonderful
(108 reviews)
Welcome to The new Star, 5 bedrooms , 4 bathrooms southfacing pool and spa
Kissimmee, FL
10% off
Price is AU$2,870
AU$2,870
AU$410 per night
includes taxes & fees
Image gallery for Private South Facing Pool w/ Jacuzzi & Kiddy pool - 4 bed, 3 bath
1010 out of 10 rating
Exceptional
(31 reviews)
Private South Facing Pool w/ Jacuzzi & Kiddy pool - 4 bed, 3 bath
Kissimmee, FL
5% off
Price is AU$3,004
AU$3,004
AU$429 per night
includes taxes & fees
Image gallery for Spacious Villa with private pool and gameroom ! ( King / King / Queen/ 2 Twins )
9.89.8 out of 10 rating
Exceptional
(87 reviews)
Spacious Villa with private pool and gameroom ! ( King / King / Queen/ 2 Twins )
Kissimmee, FL
8% off
Price is AU$2,636
AU$2,636
AU$377 per night
includes taxes & fees
Image gallery for South Saltwater Pool/Spa - free pool heat - no rear neighbors- 2 miles to Disney
9.89.8 out of 10 rating
Exceptional
(24 reviews)
South Saltwater Pool/Spa - free pool heat - no rear neighbors- 2 miles to Disney
Kissimmee, FL
7% off
Price is AU$7,883
AU$7,883
AU$1,126 per night
includes taxes & fees
Image gallery for Luxurious Pool Villa, Minutes From Walt Disney World
1010 out of 10 rating
Exceptional
(5 reviews)
Luxurious Pool Villa, Minutes From Walt Disney World
Kissimmee, FL
8% off
Price is AU$3,101
AU$3,101
AU$443 per night
includes taxes & fees
Image gallery for ☆ Location matters! Private palm paradise view from pool - 1 block to waterpark
1010 out of 10 rating
Exceptional
(14 reviews)
☆ Location matters! Private palm paradise view from pool - 1 block to waterpark
Kissimmee, FL
8% off
Price is AU$5,305
AU$5,305
AU$758 per night
includes taxes & fees
Image gallery for 2 King Ensuite on First Floor with Very Private Pool 5BD/5BA 10% Discount!
9.89.8 out of 10 rating
Exceptional
(39 reviews)
2 King Ensuite on First Floor with Very Private Pool 5BD/5BA 10% Discount!
Kissimmee, FL
6% off
Price is AU$3,653
AU$3,653
AU$522 per night
includes taxes & fees
Image gallery for 3 Miles to Disney; Game Room, 100 Yards from Community Center
9.69.6 out of 10 rating
Exceptional
(35 reviews)
3 Miles to Disney; Game Room, 100 Yards from Community Center
Kissimmee, FL
5% off
Price is AU$3,029
AU$3,029
AU$433 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 rating
Exceptional
(9 reviews)
Happy Thoughts Windsor Hills Resort 6BR Villa Private Heated Pool Spa Gameroom
Kissimmee, FL
7% off
Price is AU$3,837
AU$3,837
AU$548 per night
includes taxes & fees
Image gallery for 4-bedroom villa just 9 minutes to Walt Disney World® Resort
8.28.2 out of 10 rating
Very good
(10 reviews)
4-bedroom villa just 9 minutes to Walt Disney World® Resort
Kissimmee, FL
15% off
Price is AU$2,007
AU$2,007
AU$287 per night
includes taxes & fees
Image gallery for 5 Star - Always free pool heat and Wifi
9.69.6 out of 10 rating
Exceptional
(138 reviews)
5 Star - Always free pool heat and Wifi
Kissimmee, FL
7% off
Price is AU$2,519
AU$2,519
AU$360 per night
includes taxes & fees
Image gallery for Magical Memories 5-Bedroom Pool Home
8.88.8 out of 10 rating
Excellent
(5 reviews)
Magical Memories 5-Bedroom Pool Home
Kissimmee, FL
7% off
Price is AU$2,669
AU$2,669
AU$381 per night
includes taxes & fees
Image gallery for Luxury Lakeside Disney Villa
1010 out of 10 rating
Exceptional
(43 reviews)
Luxury Lakeside Disney Villa
Kissimmee, FL
7% off
Price is AU$8,023
AU$8,023
AU$1,146 per night
includes taxes & fees
Image gallery for Flexible Cancellation Policy-Upgraded 4-Bed/4 Bath, Pool/Spa 2 Miles to Disney
1010 out of 10 rating
Exceptional
(112 reviews)
Flexible Cancellation Policy-Upgraded 4-Bed/4 Bath, Pool/Spa 2 Miles to Disney
Kissimmee, FL
8% off
Price is AU$4,474
AU$4,474
AU$639 per night
includes taxes & fees
Image gallery for Dreaming of Disney? Luxury 3 Bedroom Condo-3 Miles from Disney
9.69.6 out of 10 rating
Exceptional
(12 reviews)
Dreaming of Disney? Luxury 3 Bedroom Condo-3 Miles from Disney
Kissimmee, FL
11% off
Price is AU$1,393
AU$1,393
AU$199 per night
includes taxes & fees
Image gallery for 7BRThemed - Poolside BBQ - Pool Heat - Near Disney
9.69.6 out of 10 rating
Exceptional
(5 reviews)
7BRThemed - Poolside BBQ - Pool Heat - Near Disney
Kissimmee, FL
8% off
Price is AU$4,462
AU$4,462
AU$637 per night
includes taxes & fees
Image gallery for Themed Room Lake Retreat Near Disney Magic
8.28.2 out of 10 rating
Very good
(20 reviews)
Themed Room Lake Retreat Near Disney Magic
Kissimmee, FL
7% off
Price is AU$3,044
AU$3,044
AU$435 per night
includes taxes & fees
Image gallery for 2024-2026- Inquire now for more details and information
9.69.6 out of 10 rating
Exceptional
(107 reviews)
2024-2026- Inquire now for more details and information
Kissimmee, FL
6% off
Price is AU$2,530
AU$2,530
AU$361 per night
includes taxes & fees
Image gallery for Welcome to Star Wars Villa, 3 miles from Disney World, private pool/spa, wifi
9.29.2 out of 10 rating
Wonderful
(26 reviews)
Welcome to Star Wars Villa, 3 miles from Disney World, private pool/spa, wifi
Kissimmee, FL
9% off
Price is AU$2,454
AU$2,454
AU$351 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 rating
Wonderful
(9 reviews)
Family Paradise w/ Pvt Pool, BBQ Grill, Themed Bedrooms, Game Room & Club access
Kissimmee, FL
14% off
Price is AU$3,122
AU$3,122
AU$446 per night
includes taxes & fees
Image gallery for Upscale WINDSOR HILLS Private Villa ♥ Pool/Spa, GAME ROOM ♥ 4 mi to DISNEY WORLD
1010 out of 10 rating
Exceptional
(45 reviews)
Upscale WINDSOR HILLS Private Villa ♥ Pool/Spa, GAME ROOM ♥ 4 mi to DISNEY WORLD
Kissimmee, FL
7% off
Price is AU$3,076
AU$3,076
AU$439 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
Showing deals for: 28 Sept - 1 Oct
Resort Style Living 2 miles from Disney World
Sleeps 8 · 3 bedrooms · 3 bathrooms
9.29.2 out of 10
Wonderfulwonderful
93 reviews(93 reviews)
The current price is AU$917
AU$917
for 3 nights, 1 home
AU$306 per night
includes taxes & fees
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
64 reviews(64 reviews)
The current price is AU$1,321
AU$1,321
for 3 nights, 1 home
AU$440 per night
includes taxes & fees
Upscale WINDSOR HILLS Private Villa ♥ Pool/Spa, GAME ROOM ♥ 4 mi to DISNEY WORLD
Sleeps 11 · 5 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
45 reviews(45 reviews)
The current price is AU$1,689
AU$1,689
for 3 nights, 1 home
AU$563 per night
includes taxes & fees
Family Friendly Windsor Hills 5BR/5BA Villa-SW Facing Pool, 2 mi. from Disney
Sleeps 11 · 5 bedrooms · 5 bathrooms
9.89.8 out of 10
Exceptionalexceptional
98 reviews(98 reviews)
The current price is AU$1,538
AU$1,538
for 3 nights, 1 villa
AU$513 per night
includes taxes & fees
Windsor Hills Resort Home with Private Pool , 5 Mins from Disney
Sleeps 13 · 7 bedrooms · 4 bathrooms
8.88.8 out of 10
Excellentexcellent
9 reviews(9 reviews)
The current price is AU$1,380
AU$1,380
for 3 nights, 1 home
AU$460 per night
includes taxes & fees
Tequilla Sunrise at Windsor Hills
Sleeps 6 · 3 bedrooms · 3+ bathrooms
9.49.4 out of 10
Exceptionalexceptional
65 reviews(65 reviews)
The current price is AU$997
AU$997
for 3 nights, 1 home
AU$332 per night
includes taxes & fees
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.