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Key West Winter Rentals & Cabins

Discover winter rentals Key West - We found 2389 exact matches

About Key West Winter Rental on Cabinns.ca

At Cabinns.ca, we feature a wide range of listings for accommodations in Key West, FL that are perfect for your winter trip or seasonal escape. Our listings include hotels, private vacation homes, cabins, condos, villas, resorts, or pet-friendly apartments that travelers are sure to love. Cabinns.ca winter vacation homes have top amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Whether you are escaping the snow or running to it, Cabinns.ca helps connect you to the best cabins, bungalows, lodges, and rent-by-owner homes, as well as the best places to stay in both sun and ski resorts. Cabinns.ca will make your winter getaway an unforgettable experience.

Cabinns.ca offers luxury finds for travelers planning on renting a place in Key West, to enjoy these benefits and to book your winter vacation homes, go to the Cabinns.ca filter option, enter your travel date, check the filters to narrow down your property type and amenities, then choose from a long list of incredible winter vacation rentals without hassle. Our interactive map is also available, so you can view destinations spanning the globe or around Key West and unlock even more amazing deals. Stay Close to Nature with Cabinns.ca.

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Frequently Asked Questions About Key West Winter Rentals

There are a lot of options in Key West. If you plan on staying in the Key West area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Key West:

The average cost for winter rentals in Key West is $776 per night. Cabinns.ca has a wide list of great winter places to stay near Key West that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage/chalet rentals in Key West that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Key West on Cabinns.ca

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Key West to find what works for you.
As of 2026, the data from Cabinns.ca shows that there are over 2389 private swimming pools or indoor pools accommodations near Key West along with other great amenities.

About 2389 holiday rentals in Key West boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:

Yes, there are many luxury places to stay in Key West for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Key West with all the best amenities for your next trip.