Understanding Key West Rentals

The beautiful island of Key West measures two miles wide and four miles long. While seemingly small, there are many rental options available to make your ideal Key West vacation happen.

First, choose your length of stay from three days to a week to even extended stays of 28 days or longer. Then, select the Key West neighborhood that best suits you. We have homes and condos located in the Historic Old Town neighborhood and condos and villas close to the beaches. We even have pet-friendly homes in case you want to explore the island with your four-legged bestie. Combine your length of stay to your favorite neighborhood to find your perfect Key West home.


Here's a closer look at each rental type:


Historic District

A vacation rental in the coveted Historic District will put you within walking distance of Duval Street, the Ernest Hemingway Home & Museum, dozens of bars and restaurants, quaint shops, and art galleries. We have lots of rental properties available near all parts of Duval Street, and we have one that's perfect for you. Browse all our Historic District vacation rentals here.

Near Beach

Chances are your ideal Key West vacation includes some sun and sand. If you prefer to sip your morning coffee while peering out on the ocean and be steps away from the beach- we have the hot spots for you! Take a look at our properties located near the beautiful Key West beaches. 

Weekly Rental

Are you looking for your perfect Key West Vacation experience? We have various properties to meet everyone's need for stays of 6 nights or longer. Enjoy the very best of Key West! Browse our property rentals below and find the vacation home that is perfect for you!

Our standard stay is 6 nights unless otherwise required by the governing condominium association. We may consider a shorter stay (no less than 3 nights) within 30 days of the requested dates if the property allows it.


Monthly Rental

Are you looking to visit Key West, Florida for an extended period of time? We have properties available for monthly rentals.

Whether your down for business, or for a tropical vacation, we have the right rental property for you. Browse through our collection of monthly rentals located in the Historic District and/or near the beautiful beaches.

Pet Friendly

Looking to bring the family pet with you on vacation?  The individual owners of the properties set the rules on what pets they will accept.  This should be a starting guide for you in your selection process to find your vacation home.  From here please contact us with respect to size and other requirements set by the owner.

Please note that most condominiums do not allow pets.