Windsor Hills holiday rentals
We found 2,751 holiday rentals — enter your dates for availability
Select from 976 houses, 325 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:12 Sept - 19 Sept
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$7,934
AU$7,934
AU$1,133 per night
includes taxes & fees
Image gallery for MAJESTIC RETREAT - THEATRE, SPLASH PAD!, MICKEY POOL!, HOT TUB DISNEY 2 mi
1010 out of 10 rating
Exceptional
(25 reviews)
MAJESTIC RETREAT - THEATRE, SPLASH PAD!, MICKEY POOL!, HOT TUB DISNEY 2 mi
Kissimmee, FL
8% off
Price is AU$5,586
AU$5,586
AU$798 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
(38 reviews)
2 King Ensuite on First Floor with Very Private Pool 5BD/5BA 10% Discount!
Kissimmee, FL
6% off
Price is AU$3,192
AU$3,192
AU$456 per night
includes taxes & fees
Image gallery for Disney theme rooms,Splashpad, Movie Theater, Private Pool
1010 out of 10 rating
Exceptional
(219 reviews)
Disney theme rooms,Splashpad, Movie Theater, Private Pool
Kissimmee, FL
7% off
Price is AU$5,728
AU$5,728
AU$818 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
(116 reviews)
RATED#1 BEST HOME Near Disney! LUXURY 5BEDROOM 5Bath VILLA ,GATED RESORT ,POOL
Kissimmee, FL
7% off
Price is AU$3,157
AU$3,157
AU$451 per night
includes taxes & fees
Image gallery for Formosa luxury villa - Welcome to The Oasis
9.89.8 out of 10 rating
Exceptional
(8 reviews)
Formosa luxury villa - Welcome to The Oasis
Kissimmee, FL
7% off
Price is AU$7,758
AU$7,758
AU$1,108 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
7% off
Price is AU$3,842
AU$3,842
AU$549 per night
includes taxes & fees
Image gallery for Family Wanted: For fun, sun, & making memories! Free BBQ & spa heat too!
9.89.8 out of 10 rating
Exceptional
(110 reviews)
Family Wanted: For fun, sun, & making memories! Free BBQ & spa heat too!
Kissimmee, FL
7% off
Price is AU$3,675
AU$3,675
AU$525 per night
includes taxes & fees
Image gallery for Blue Belle - Minutes to Disney - Heated Pool- Luxury Home
1010 out of 10 rating
Exceptional
(5 reviews)
Blue Belle - Minutes to Disney - Heated Pool- Luxury Home
Kissimmee, FL
8% off
Price is AU$7,495
AU$7,495
AU$1,071 per night
includes taxes & fees
Image gallery for Awesome new dram vacation home 5 min. from Disney
1010 out of 10 rating
Exceptional
(14 reviews)
Awesome new dram vacation home 5 min. from Disney
Kissimmee, FL
7% off
Price is AU$2,983
AU$2,983
AU$426 per night
includes taxes & fees
Image gallery for Big Pool&Spa/Themed rooms/Private yard/ CLOSE TO EVERYTHING, Lakeview,Playground
1010 out of 10 rating
Exceptional
(151 reviews)
Big Pool&Spa/Themed rooms/Private yard/ CLOSE TO EVERYTHING, Lakeview,Playground
Kissimmee, FL
7% off
Price is AU$4,030
AU$4,030
AU$576 per night
includes taxes & fees
Image gallery for 3. Magical Disney Dream Townhouse!
9.69.6 out of 10 rating
Exceptional
(5 reviews)
3. Magical Disney Dream Townhouse!
Kissimmee, FL
7% off
Price is AU$2,109
AU$2,109
AU$301 per night
includes taxes & fees
Image gallery for ✨Remodeled Luxury Retreat with Pool-Steps to Clubhouse! 🪄NEW Harry Potter Room!✨
1010 out of 10 rating
Exceptional
(72 reviews)
✨Remodeled Luxury Retreat with Pool-Steps to Clubhouse! 🪄NEW Harry Potter Room!✨
Kissimmee, FL
7% off
Price is AU$2,355
AU$2,355
AU$336 per night
includes taxes & fees
Image gallery for 3 Miles from Disney!!!!! 4 Bedroom Villa with Private Pool/Game Room
1010 out of 10 rating
Exceptional
(15 reviews)
3 Miles from Disney!!!!! 4 Bedroom Villa with Private Pool/Game Room
Kissimmee, FL
7% off
Price is AU$2,850
AU$2,850
AU$407 per night
includes taxes & fees
Image gallery for Free Pool Heat and BBQ! No Rear Neighbors! South Facing Pool!-AC Game Room!
9.89.8 out of 10 rating
Exceptional
(91 reviews)
Free Pool Heat and BBQ! No Rear Neighbors! South Facing Pool!-AC Game Room!
Kissimmee, FL
9% off
Price is AU$3,045
AU$3,045
AU$435 per night
includes taxes & fees
Image gallery for 4mi to Disneyworld
9.29.2 out of 10 rating
Wonderful
(5 reviews)
4mi to Disneyworld
Kissimmee, FL
7% off
Price is AU$2,228
AU$2,228
AU$318 per night
includes taxes & fees
Image gallery for Near Disney With A Private Pool-New House ECOLAB SANITIZED, FENCED POOL
9.29.2 out of 10 rating
Wonderful
(43 reviews)
Near Disney With A Private Pool-New House ECOLAB SANITIZED, FENCED POOL
Kissimmee, FL
5% off
Price is AU$4,184
AU$4,184
AU$598 per night
includes taxes & fees
Image gallery for Serene & Clean Pool House 8 mins to Disney
8.68.6 out of 10 rating
Excellent
(10 reviews)
Serene & Clean Pool House 8 mins to Disney
Kissimmee, FL
11% off
Price is AU$2,484
AU$2,484
AU$355 per night
includes taxes & fees
Image gallery for ☀️6 BED VILLA - POOL & SPA - BBQ - GAMES ROOM -MILITARY DISCOUNT All DAY SUN
9.69.6 out of 10 rating
Exceptional
(111 reviews)
☀️6 BED VILLA - POOL & SPA - BBQ - GAMES ROOM -MILITARY DISCOUNT All DAY SUN
Kissimmee, FL
8% off
Price is AU$3,322
AU$3,322
AU$475 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
(36 reviews)
Star Wars Themed BR Free Resort Waterpark and Pool Heat 2.5 miles to Disney
Kissimmee, FL
7% off
Price is AU$2,255
AU$2,255
AU$322 per night
includes taxes & fees
Image gallery for FREE: Waterpark, South facing pool, Game room, Themed rooms, 2 Miles to Disney.
9.69.6 out of 10 rating
Exceptional
(138 reviews)
FREE: Waterpark, South facing pool, Game room, Themed rooms, 2 Miles to Disney.
Kissimmee, FL
8% off
Price is AU$3,065
AU$3,065
AU$438 per night
includes taxes & fees
Image gallery for Resort Style Living 2 miles from Disney World
9.29.2 out of 10 rating
Wonderful
(93 reviews)
Resort Style Living 2 miles from Disney World
Kissimmee, FL
7% off
Price is AU$1,762
AU$1,762
AU$252 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
(60 reviews)
Sun filled south facing pool & spa with no rear neighbors! Game room!
Kissimmee, FL
7% off
Price is AU$3,590
AU$3,590
AU$513 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$2,844
AU$2,844
AU$406 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: 12 Sept - 15 Sept
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$971
AU$971
for 3 nights, 1 home
AU$324 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
Fabulous Lake View/South Facing Pool Home- Game room -2 Miles to Disney!
Sleeps 10 · 5 bedrooms · 5 bathrooms
8.88.8 out of 10
Excellentexcellent
179 reviews(179 reviews)
The current price is AU$1,633
AU$1,633
for 3 nights, 1 home
AU$544 per night
includes taxes & fees
Tequilla Sunrise at Windsor Hills
Sleeps 6 · 3 bedrooms · 3+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
64 reviews(64 reviews)
The current price is AU$998
AU$998
for 3 nights, 1 home
AU$333 per night
includes taxes & fees
Welcome To Magnolia Blossom Villa! South Facing Pool in Prime Location.
Sleeps 14 · 6 bedrooms · 4 bathrooms
9.89.8 out of 10
Exceptionalexceptional
50 reviews(50 reviews)
The current price is AU$1,714
AU$1,714
for 3 nights, 1 villa
AU$571 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$1,673
AU$1,673
for 3 nights, 1 villa
AU$558 per night
includes taxes & fees
Top rated rentals - Windsor Hills
Great range of bedrooms for everyone
1010 out of 10
Exceptionalexceptional
44 reviews(44 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.