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Florida Keys Beaches Cottage Rentals & Holiday Homes

Find the best cottages in Florida Keys Beaches - We found 105 exact matches

About Florida Keys Beaches Cottage Rentals on PickleTrip

Searching for cottages to rent near Florida Keys Beaches? PickleTrip™ features more than 105 cottages that are perfect for your next pickleball getaway. Plan your ultimate holiday and discover luxury cottage rentals that are a few miles away from the lake or beach and have access to private courts or nearby facilities. These cottage rentals in Florida Keys Beaches have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. PickleTrip™’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Florida Keys Beaches.

Are you planning to travel to the lakeside, beach, or mountain area? PickleTrip™’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.

PickleTrip™ boasts of 105 holiday cottages and places to stay in Florida Keys Beaches. The site provides unique Airbnb, VRBO, pickleball-ready cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday — all fitting within your budget.

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Frequently Asked Questions About Florida Keys Beaches Rental Cottages

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

Yes, here are the top cottage rentals in Florida Keys Beaches that allow you to bring your pet:

See all pet-friendly vacation rentals in Florida Keys Beaches on PickleTrip

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Florida Keys Beaches to find one that works for you.
As of 2026, the data from PickleTrip shows that there are Over 105 private swimming pools or cottages with indoor pools in the Florida Keys Beaches area along with other great amenities.
About 105 cottages in Florida Keys Beaches boast of premium hot tubs. Some of the popular places to stay with hot tubs include:See all holiday vacation rentals in Florida Keys Beaches on PickleTrip
Yes, there are luxury cottages in Florida Keys Beaches. Find more luxury, lakefront, winter, & last-minute cottage rentals near Florida Keys Beaches.