Windward Cay vacation rentals

We found 1,377 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 16 homes, 14 villas, and vacation rentals in Windward Cay that are perfect for your trip. Whether you’re staying in a vacation home with family, friends, or just your furry companion, you'll have the amenities you expect and more, including parking and a TV. Whatever you're looking for, you'll be sure to find a rental to meet everyone's needs, including accessible or non-smoking choices.

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Frequently asked questions

What is the most popular type of vacation 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 vacation 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 vacation rental in Windward Cay?

The average price for a vacation 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 traveling. 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 vacation rentals in Windward Cay?

Yes. You can pick from 24 vacation rentals that cater to pets in Windward Cay. Lots of our pet-friendly vacation 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 vacation 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 vacation 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 vacation homes include the best amenities for hanging out with the people you love.

Are there large group vacation 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 vacation rentals in Windward Cay that welcome kids?

Windward Cay has 24 family-friendly vacation 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 vacation 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 vacation homes with WiFi in Windward Cay. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.

How can I find vacation rentals with air conditioning in Windward Cay?

Windward Cay has 23 vacation 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 vacation rental in Windward Cay?

You'll need to check with the Windward Cay vacation home you're looking at on Vrbo as age restrictions differ. However, generally it's 16, 18 or 21.

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