Monthly Vacation Rentals in Key West

Historic Key West Vacation Rentals' monthly vacation rental properties are the perfect option for an extended stay in our tropical paradise of Key West. Our Key West Monthly Vacation rentals require 28-night minimums. Please keep this in mind when selecting your dates to be sure you meet this minimum night stay rule in order to bring up available options (due to strict city regulations, no exceptions may be made to the minimum stay). Immerse yourself in the warm and tropical paradise all month long and experience all that local living in Key West can offer.  Browse our collection of luxury Key West vacation rentals to make your stay a breeze so that you can unwind and experience the best of the Florida Keys!


Discounts are often available for Key West monthly vacation rentals, especially in the off-season or if staying for multiple months, so please ask! Monthly vacation rentals include utilities such as electricity, water, and propane. Please read our rental policies for other rules & items specifically related to our monthly rentals.

Reservations occurring during "Peak Season" require check-in dates on the 1st of the month and can only be rented in monthly increments.