Let us be your ticket to paradise. Historic Hideaways manages and rents the finest vacation homes in Key West — from private homes with their own pools, to cozy cottages, condominiums, and townhomes, most with pools, in Old Town, Truman Annex, The Meadows, Casa Marina, and Mid & New Town. Homes run from one bedroom to four-plus, many are dog-friendly,... Read More about Historic Hideaways

Ambrosia Key West is a relaxed, pet-friendly bed-and-breakfast comprising several cottages in Old Town Key West's heart, just two blocks from Duval Street. Individually decorated rooms feature themed decor and free Wi-Fi, plus minifridges, microwaves, and coffeemakers. Suites might include 4-poster canopy beds and whirlpool tubs. Private, 2-bedroom cottages add full kitchens and separate living areas. A hot breakfast buffet... Read More about Ambrosia Key West

These three, iconic historic homes including the Bahamian Eyebrow Building, part of the National Registry of Historic Places are a treasure trove of stories. Nestled behind classic picket fences, Ridley House beckons you for a one-of-a-kind stay where Key West’s bohemian vibes meet upscale stays in a prime location.

Originally built in 1911, Weatherstation Inn is excited to have recently joined the Ocean Breeze Inns collection of breezy Florida hotels and resorts. But – with no changes in ownership or operations – we’re still the same adults-only bed and breakfast you know and love, tucked away in a privately gated community in a historic Key West Navy Yard. Experience... Read More about The Weatherstation Inn

The only all male guesthouse on Duval Street. Part of the Bourbon Street Pub complex. Free breakfast, free happy hour, free gym, free wifi, free cover at the Bourbon Street Pub and the 801. Stay where you play!

Enchantment awaits in the vibrant center of Old Town, just steps from Duval Street and the best of Key West. Discover our inviting resort-like retreat where every room is unique and each stay is unforgettable. Playful, expansive and exceptionally lush, with timeless historical architecture and three sun-dappled pools.