Windward Cay holiday rentals

We found 1,362 holiday rentals — enter your dates for availability

Discover a selection of holiday rentals in Windward Cay that are perfect for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a washer and dryer. Whatever you're looking for, you'll find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Windward Cay

Showing deals for:15 May - 22 May

Image gallery for 8BR/5BA pool home,Near Disney,SeaWorld,Convention Center

8br/5ba 3680sqft pool villa
9.0 out of 10, Wonderful, (15 reviews)
Wonderful
(15 reviews)

8BR/5BA pool home,Near Disney,SeaWorld,Convention Center

Kissimmee

22% off
Price is S$2,315
for 7 nights, 1 home
S$331 per night
includes taxes & fees
8BR/5BA pool home,Near Disney,SeaWorld,Convention Center

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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

What is the most popular type of holiday rental accommodation in Windward Cay?
According to our research, villas are the most in-demand type of property in Windward Cay. But as you might expect, everyone's idea of an epic stay can differ. Vrbo has holiday homes in a variety of sizes and shapes, so you're sure to discover your ideal match.
How much does it cost to rent a holiday rental in Windward Cay?
The average price for a holiday rental in Windward Cay is determined by a number of factors, like length of stay, property type and season. Whether you prefer a sprawling villa with lots of bedrooms or a quaint cabin for you and your other half, just add your travel dates to discover stays that offer great value.
How much does it cost to rent a beach house in Windward Cay?
Prices for beach houses in Windward Cay can differ depending on the size and style of the property and when you're travelling. Just enter your travel dates into Vrbo and how many guests to view your rental options and prices. From there you can use the filters to narrow down your search by nearby activities, ratings, amenities and more.
Are there pet-friendly holiday rentals in Windward Cay?
Yes. You can pick from 24 holiday rentals that cater to pets in Windward Cay. Lots of our pet-friendly holiday rentals even have an area outdoors for your four-legged pal to play around in, doggie beds, complimentary treats and proximity to parks or green space. Apply the "Pets allowed" filter to find your pawfect holiday home on Vrbo.
Can I rent a house with a pool in Windward Cay?
Pack your swimwear and inflatable flamingo, because there are 23 houses with a private pool in Windward Cay. Unwind at one of these terrific holiday rentals and every day will be a pool day. Simply enter your travel dates into Vrbo, then check the "pool" filter to find the perfect place to make a splash!
What are popular rental amenities in Windward Cay?
The most popular rental amenities people look for in Windward Cay include nearby museums, a barbecue grill and a lake view. Whether you're on a trip with family, your besties or even pets, Vrbo holiday homes include the best amenities for hanging out with the people you love.
Are there large group holiday rentals in Windward Cay?
Take your pick of 17 Vrbo properties in Windward Cay that can host five or more guests. You'll enjoy all the privacy and room you need to kick back with your nearest and dearest — and no one else.
Are there holiday rentals in Windward Cay that welcome kids?
Windward Cay has 24 family-friendly holiday homes. And tracking down a stay that welcomes children is a cinch with Vrbo's "Properties good for families" filter. On top of having the entire place to yourselves, you'll get access to perks and conveniences like bunk beds, kitchens and private pools.
What are the top attractions for families in Windward Cay?
Keeping the kids occupied during your stay in Windward Cay is a breeze with these exciting family-friendly attractions:

  • Fun Spot America
  • Island H2O Live!
  • Kissimmee Go-Karts

Are there holiday rentals with WiFi in Windward Cay?
Whether you'd like to keep up with the headlines, send some emails or update your social media, there are seven holiday homes with WiFi in Windward Cay. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.
How can I find holiday rentals with air conditioning in Windward Cay?
Windward Cay has 23 holiday rentals where you can chill out in air-conditioned comfort. To find a stay on Vrbo that comes with this perk, enter your desired travel dates and use the handy filter tool to select the "air conditioning" box.
How old do you have to be to rent a holiday rental in Windward Cay?
You'll need to check with the Windward Cay holiday home you're looking at on Vrbo as age restrictions differ. However, generally it's 16, 18 or 21.
How long can I rent a holiday rental in Windward Cay for?
The amount of time you can stay in a Windward Cay holiday rental for differs depending on the property. Simply enter your preferred travel dates to browse available options that offer extended stays. They feature all the things you need to make your extended getaway more enjoyable and convenient, like kitchens and air conditioning. Some holiday homes might also offer weekly or monthly discounted prices, so you can have a longer stay for less.

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