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Florida Keys Winter Rentals & Holiday Homes

Discover winter rentals Florida Keys - We found 220 exact matches

Frequently Asked Questions About Florida Keys Winter Rental

What are the top rated Winter Rentals in Florida Keys?

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

How much does it cost to rent a place to stay near Florida Keys in the wintertime?

The average cost for winter rentals in Florida Keys is $966 per night. Luxurysicilyvilla has a wide list of great winter places to stay near Florida Keys that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.

Are there any winter cottages/chalets in Florida Keys that allow pets?

Yes, here are the top cottage/chalet rentals in Florida Keys that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Florida Keys on Luxurysicilyvilla

Do you have any winter rentals in Florida Keys that are suitable for families?

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Florida Keys to find what works for you.

Are there winter accommodations in Florida Keys that have indoor swimming pools?

As of 2026, the data from Luxurysicilyvilla shows that there are over 220 private swimming pools or indoor pools accommodations near Florida Keys along with other great amenities.