752+ Luxury Vacation Rentals & Cabins in Windley Key |
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Windley Key Cabin Rentals

About Windley Key Vacation Rentals

There are more than 752 incredible getaway rentals that are available in Windley Key. These choices include cabins, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Stay Close to Nature with Cabinns.ca and uncover great stays in Windley Key.

Cabinns.ca features numerous last-minute deals on private villas, hotels, and cabin rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With Cabinns.ca in Windley Key, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the Cabinns.ca vacation rentals, resorts, and Airbnb-style properties in Windley Key. Places to stay near Windley Key are 720.72 ft² on average, with prices averaging CA $1,026 a night.

Cabinns.ca helps you find the ideal holiday rental to create a lifetime of travel memories in Windley Key. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect cabin retreat today.

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Top Cabin Rentals, Cottages, and Holiday Home Rentals in Windley Key

Type Count
Vacation Homes 498
Holiday Apartments 70
Villas 34
Others 12
Cottages 6
Unique Vacation Rentals 5

Use these Quick Filters to Find a Vacation Rental in Windley Key

★ Pro Tip: Cabinns.ca is a cabin vacation rental website, pulling some of the top cabins, luxury resorts, and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible cabin resorts and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Windley Key with Cabinns.ca.

Weather in Windley Key, FL

View the weather forecast for Windley Key before booking your Windley Key Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Activities Windley Key Guest Reviews Local Attractions

A Large Selection of Cabins and Vacation Rentals from Around the World Windley Key. Discover Top Attractions For Your Next Outdoor Adventure.


Theater of the Sea
Windley Key Fossil Reef Geological State Park
John Pennekamp Coral Reef State Park
Jimmy Johnson's Big Chill
Key Largo Undersea Park
Dolphins Plus Bayside
Dolphin Cove
Bud n' Mary's Dive Center
Founders Park
Anne's Beach
Caribbean Club Bar
Dolphins Plus
Harry Harris Park
Bluefin Rock Harbor Marina
Florida Keys Dive Center
Harry Harris Park
Florida Keys Flats Fishing
Islamorada County Park
Fiesta Key
Florida Keys Wild Bird Rehabilitation Center

Find Nearby Cabin Rentals in these Cities & Neighborhoods


Theater of the Sea 738 Properties
Windley Key Fossil Reef Geological State Park 726 Properties

Frequently Asked Questions About Windley Key?

What are the top cabins, lake houses & summer homes in Windley Key?

We provide an array of great vacation destinations in Windley Key. If you are looking to stay in or around the Windley Key area, make sure to browse our options to find a premium cabin resort or rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Windley Key:

How many cabin rentals and resorts have private pools in Windley Key?

We have 116 cabins, luxury resorts, and holiday home rentals featuring a private pool in and near Windley Key. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which cabin rental, resort, or holiday home in Windley Key is best for families?

Searching for a family-friendly cabin in Windley Key? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfectly fit families of all sizes.

How many hotels, resorts, or cabin rentals are available in Windley Key?

Cabinns.ca offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Cabinns.ca in 2025 is over 752 in the Windley Key area, and that number rises every day. By combining listings from multiple websites and travel providers, Cabinns.ca can provide you with a diverse amount of choices of the best luxury stays in Windley Key.

Nearby Neighborhood (1) 
Neighborhood Property Count
Venetian Shores Rental Cabins and Private Getaways in Florida 47

People Also Ask

There are 70 hotels in Windley Key 29 resorts, and 602 rentals

Recently Booked Private Villas, Cabin Resorts, and Rentals Windley Key