Historic Key West Vacation Rentals

Historic Key West Vacation Rentals has been placing visitors in Key West houses since 2011. It is a local operation, owned by Key West broker Brenda Donnelly and run from an office on White Street, which means the person recommending a neighborhood to you has probably walked it that morning.

The portfolio runs across seven parts of the island, each with a different personality. Historic Old Town for the gingerbread porches and the walk to everything. Bahama Village for the Cuban bakeries and roosters. Truman Annex for gated quiet beside Fort Zachary Taylor. The Meadows and Mid Town for residential streets where you will meet actual neighbors. Casa Marina for the old resort end of the island near the water. And Sunset Key, a private island a short boat ride off the harbor, for when you want the lights of Duval visible but comfortably far away. Properties include whole houses, cottages, condos, townhouses, duplexes and apartments, in sizes that suit a couple or a family reunion.

You can book a few nights or settle in for a month. The agency keeps a separate category for 30 day stays, which is the sensible route for snowbirds and anyone working remotely through the winter, and nightly stays for the properties licensed to take them.

They hold memberships in the Key West Chamber of Commerce, the Key West Business Guild and the Vacation Rental Management Association, and carry Airbnb Superhost and Vrbo Premier Host status. Call the office and tell them what kind of trip you are after, and they will point you at the right street before they point you at the house.