Windley Key holiday rentals

We found 1,375 holiday rentals — enter your dates for availability

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Book a holiday rental for your Windley Key getaway

Learn about the unique charm of Windley Key with a stay in a holiday home rental. This city has something for everyone. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Exploring the natural features in Windley Key

Whether you're looking for adventure or just want to take in the scenery, Windley Key is a great place to get out in nature. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Everglades National Park (29.9 mi / 48.1 km)
  • Islamorada County Park (1.5 mi / 2.5 km)
  • Founders Park (1.6 mi / 2.6 km)
  • Anne's Beach (11.8 mi / 19 km)
  • Fiesta Key (14.8 mi / 23.8 km)
  • Windley Key Fossil Reef Geological State Park (0.7 mi / 1.1 km)

Frequently asked questions

What is the most popular type of holiday home accommodation in Windley Key?
The most popular types of holiday homes in Windley Key are houses. Prefer something different? Stayz has plenty of options to match our guests’ unique needs, so you’ll see holiday homes in loads of sizes and shapes. The perfect fit is ready and waiting for you — lock in yours today.
How much does it cost to rent a holiday home in Windley Key?
Several things affect the price of a holiday home in Windley Key, like the time of year, length of stay and property type. Still, all of our holiday homes have something in common — incredible value. Just enter your travel dates to find your home away from home.
How much does it cost to rent a beach house in Windley Key?
Prices for beach houses in Windley Key vary depending on the size and type of the property and when you plan to travel. All you need to do is enter your travel dates into Stayz and the number of guests to see your home options and prices. From there you can use the filters to narrow down your search by ratings, amenities and more.
What are popular home amenities in Windley Key?
A washing machine, a fridge and off-street parking options are the most popular home amenities in Windley Key. Whether you’re heading away solo, with your sweetheart or a group of best friends, Stayz will help you find a holiday home that fits your tastes with all the conveniences you’re looking for.
Are there large group holiday homes in Windley Key?
Windley Key has three holiday homes that can cater to 10 or more guests. These properties come with the space and privacy you need to enjoy good times with friends and family.
Can I find two-bedroom holiday homes in Windley Key?
You can select from 39 two-bedroom holiday properties in Windley Key. Give the kids the second room or maybe fill it with a couple of your nearest and dearest friends. There’s enough space for whoever’s fortunate enough to come along for the ride.
Are there holiday homes with WiFi in Windley Key?
Whether you’d like to keep up to date with the news, send a few emails or surf your social networks, there are 20 holiday homes with WiFi in Windley Key. Check the “WiFi” box when searching on Stayz and stay connected on your getaway.
How old do you have to be to rent a holiday home in Windley Key?
The minimum age can vary across properties on Stayz, so look at the rules of the holiday home in Windley Key you want to book. But in general, it’s 16, 18 or 21.
How long can I rent a holiday home in Windley Key for?
The amount of time you can rent a Windley Key holiday home for depends on the property. Just tap in your preferred travel dates to see available options offering extended stays. They have all the things you need to make your extended holiday more comfortable such as kitchens and backyards. Some Stayz holiday homes may also offer weekly or monthly discounted prices, so you can hang around longer for less.

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