Historic Hideaways/Key West Realty

Historic Hideaways has been renting Key West homes since 1996, which in a town where rental companies come and go is most of the useful information right there. It is locally owned and run, with about thirty-three properties on the books, and the staff answering the phone are the ones who have walked through every one of them.

The collection runs from private villas and cottages up through townhomes, condominiums and full-size houses, so it scales from a couple to a family reunion. Some have their own pool or a walled tropical courtyard, and some sit in buildings with shared resort amenities. Properties carry names rather than unit numbers, which tells you something: Paradise Grand, Truman House, Boomerang Boathouse. Most are in the Old Town Historic District, where you can walk to dinner, and some are in the gated quiet of Truman Annex.

Stays are weekly, monthly or seasonal. That shapes the trip in a good way. You unpack properly, you shop for groceries, you find the coffee place that becomes yours, and you stop looking at your watch. It also means the winter season books out early, so plan ahead if you want January.

The office is on Duval Street, and there is a separate concierge line for local advice and for booking trips and tours, which is worth calling before you arrive because the popular ones sell out.