
Windsor Hills holiday homes
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 NZ$8,739
NZ$8,739
NZ$1,248 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 NZ$6,044
NZ$6,044
NZ$863 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 NZ$3,457
NZ$3,457
NZ$494 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 NZ$6,193
NZ$6,193
NZ$885 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 NZ$3,416
NZ$3,416
NZ$488 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 NZ$8,544
NZ$8,544
NZ$1,221 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 NZ$4,163
NZ$4,163
NZ$595 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 NZ$8,256
NZ$8,256
NZ$1,179 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 NZ$3,985
NZ$3,985
NZ$569 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 NZ$3,230
NZ$3,230
NZ$461 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 NZ$4,362
NZ$4,362
NZ$623 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 NZ$2,258
NZ$2,258
NZ$323 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 NZ$3,087
NZ$3,087
NZ$441 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 NZ$2,522
NZ$2,522
NZ$360 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 NZ$3,298
NZ$3,298
NZ$471 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 NZ$2,384
NZ$2,384
NZ$341 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 NZ$4,528
NZ$4,528
NZ$647 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 NZ$2,659
NZ$2,659
NZ$380 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
7% off
Price is NZ$3,602
NZ$3,602
NZ$515 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 NZ$2,413
NZ$2,413
NZ$345 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 NZ$3,318
NZ$3,318
NZ$474 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
8% off
Price is NZ$1,875
NZ$1,875
NZ$268 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 NZ$3,893
NZ$3,893
NZ$556 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 NZ$3,082
NZ$3,082
NZ$440 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
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)
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
63 reviews(63 reviews)
*NEW* Windsor Hills - Ohana Oasis Pool Home Near Disney 4bd/4ba
Sleeps 9 · 4 bedrooms · 4 bathrooms
9.69.6 out of 10
Exceptionalexceptional
18 reviews(18 reviews)
Once Upon A Dream Villa, a beautiful 6 bed / 4 bath home in Windsor Hills Resort
Sleeps 14 · 6 bedrooms · 4 bathrooms
9.29.2 out of 10
Wonderfulwonderful
103 reviews(103 reviews)
RATED#1 BEST HOME Near Disney! LUXURY 5BEDROOM 5Bath VILLA ,GATED RESORT ,POOL
Sleeps 12 · 5 bedrooms · 5 bathrooms
9.49.4 out of 10
Exceptionalexceptional
116 reviews(116 reviews)
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)
- 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 Bookabach 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 Bookabach. 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 Bookabach, 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 Bookabach holiday homes may also offer discounted weekly or monthly prices, so you can stay longer for less money.