Old Town & Truman Annex
Truman Annex and Old Town’s alleyways hold centuries of stories—and cats—just steps from the most famous house on the island.
Walk down Eleanor Street and turn into any of the narrow, shaded alleys—they open into secret gardens with fountains, bougainvillea walls, and catnip patches. The Truman Annex was originally a naval air station, and many courtyards still hide original hangar doors or concrete runways beneath moss-draped palms. Book early if you want a place with a courtyard view: most host just eight to twelve guests, and locals know to reserve before winter rates rise.
The Hemingway House’s six-toed cats are the stars, but locals keep their own colonies—dozens of them, each with nicknames and feeding schedules. If you walk the Annex lanes before dawn, you’ll hear the soft thump of cat food bowls set down at 6 a.m. You’ll see residents checking for wet paws near porches or patching holes in screening so kits stay safe. The best coffee under two blocks of the House comes from the alley-side cart on Whitehead near Ann Street—no lines before 8 a.m., and they use local beans.
Old Town’s quiet streets hide deeper history: the Spanish Consulate on Whitehead has stood since the 1820s, and the old naval hospital now hosts low-impact art shows. Many long-term rentals here include parking—rare in Key West—and include access to shaded courtyards where neighbors share garden tools and recipe swaps. Look for units near South Street: they’re quieter than Duval-facing spots but still walkable to Mallory Square by 6 p.m.
