Windsor Hills holiday rentals

We found 2,782 holiday rentals — enter your dates for availability

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August 2025

September 2025

Select from 959 houses, 322 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:21 Nov - 28 Nov

SOUTH facing pool! Plenty of lounge chairs and tables. New pool/spa heater 2023

Exceptional

(128 reviews)

6 Bed - 4 Bath Villa SOUTH FACING POOL - 2 Miles From DISNEY - OVER 100 Reviews

Kissimmee, FL

7% off

AU$546 per night

includes taxes & fees

Exceptional

(41 reviews)

10% Discount! 2 King Ensuite on First Floor with Very Private Pool 5BD/5BA

Kissimmee, FL

7% off

AU$731 per night

includes taxes & fees

Exceptional

(24 reviews)

South Saltwater Pool/Spa - free pool heat - no rear neighbors- 2 miles to Disney

Kissimmee, FL

7% off

AU$1,145 per night

includes taxes & fees

Exceptional

(9 reviews)

Beautiful Sunsets at Windsor Hills 5/5 Home with Overlook & Minutes to the Magic

Kissimmee, FL

7% off

AU$731 per night

includes taxes & fees

Exceptional

(42 reviews)

Fun in the Sun at Mickey Hideaway Villa. Make memories & Minutes to Attractions

Kissimmee, FL

7% off

AU$582 per night

includes taxes & fees

Exceptional

(40 reviews)

Amazing 6-bedroom Villa with Private Pool Minutes from Disney! 5 Star Theming!

Kissimmee, FL

8% off

AU$775 per night

includes taxes & fees

Exceptional

(23 reviews)

Windsor Hills Resort! 6 Bedroom House, 2 miles to Disney, Private Pool & Spa🏝

Kissimmee, FL

7% off

AU$665 per night

includes taxes & fees

Enter the magical world of the Minions in our beautifully decorated bedroom

Wonderful

(9 reviews)

Family Paradise w/ Pvt Pool, BBQ Grill, Themed Bedrooms, Game Room & Club access

Kissimmee, FL

7% off

AU$692 per night

includes taxes & fees

Welcome to Retro Retreat at Windsor Hills! Minutes from the Magic!

Exceptional

(33 reviews)

Retro 50s 3BR Villa with Pool and Waterpark Access Just 2 Miles from Disney

Kissimmee, FL

7% off

AU$388 per night

includes taxes & fees

Exceptional

(56 reviews)

Large Two Story Home with TWO Master Bedrooms with attached full baths.

Kissimmee, FL

7% off

AU$527 per night

includes taxes & fees

Exceptional

(69 reviews)

😎RELAX at Windsor Hills🌴, minutes to Disney - 5 bed / 5 bath, Private Pool🌞

Kissimmee, FL

8% off

AU$544 per night

includes taxes & fees

Exceptional

(74 reviews)

6BR/4B Windsor Hills Villa, Pool & Game Room, 2 Miles from Walt Disney World

Kissimmee, FL

6% off

AU$700 per night

includes taxes & fees

Exceptional

(111 reviews)

SOUTH FACING 6 BED VILLA - POOL & SPA - GAMES ROOM - THEMED ROOMS - BBQ ☀️☀️☀️

Kissimmee, FL

8% off

AU$521 per night

includes taxes & fees

Unforgettable Disney Mickey Mouse Star Wars room at our rental

Exceptional

(38 reviews)

Star Wars Themed BR Free Resort Waterpark and Pool Heat 2.5 miles to Disney

Kissimmee, FL

8% off

AU$431 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Windsor Hills

Resort Style Living 2 miles from Disney World

Sleeps 8 · 3 bedrooms · 3 bathrooms

Once Upon A Dream Villa, a beautiful 6 bed / 4 bath home in Windsor Hills Resort

Sleeps 14 · 6 bedrooms · 4 bathrooms

TOP-RATED Windsor Hills Home ♥ THEATER ROOM, Game Room, Pool/Spa, 4 Mi to Disney

Sleeps 10 · 5 bedrooms · 5 bathrooms

A gated resort community with water slides and many facilities

Fun for kids and parents 6BR/4BA with private pool & hot tub in resort community

Sleeps 12 · 6 bedrooms · 4 bathrooms

*Special Deals! FROZEN Bedroom. Closest To Disney 6BR/4BA Pool No Rear Neighbors

Sleeps 13 · 6 bedrooms · 4 bathrooms

Top rated rentals - Windsor Hills

Air Conditioned Game Room - Billiards, Pinball, Multi-Arcade, Bubble Hockey

Premier Host

Family vacation twin granddaughters off to college in Fall.

The home is absolutely gorgeous! Ten members of my family stayed there and having 5 bedrooms and 5 bathrooms was awesome, especially with 5 girls 😊The house was very clean. Family also loved the game room there was entertainment for everyone. Plenty of space for you time if needed. Easy access to parks and other family activities. Juli one of the owners was truly accommodating with any issue or concerns. She was very pleasant and accessible. I believe my family’s stay was pleasant and hope to return. Thank you Juli (Greg was very pleasant and helpful during our stay 😊)

Patricia B.

Stayed July 2023

Premier Host

A spacious, comfortable condo

We stayed for 10 days. It was exactly as the photos depicted. A really bright and cosy condo. It was well stocked and also well located for the pool and club house while being at the end of the block so through traffic (both cars and people) were minimal. Our only complaint would be the very noisy neighbours we had above us for 9 out of 10 nights of our stay who sounded like they were tap dancing for hours on their return each evening. Now the fault of the condo but something to be aware of or to pack ear plugs. Thank you for your fantastic communication and letting us use your lovely condo.

Kate S.

Stayed Oct 2022

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More quality time
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All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More 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.