Historic Key West bed and breakfasts give visitors a more personal way to stay in Old Town, with restored island homes, charming guest rooms, tropical courtyards, porch seating, garden pools, and walkable access to Duval Street, the Historic Seaport, Mallory Square, local restaurants, galleries, museums, beaches, and nightlife. This category is designed to help guests compare Key West B&Bs, boutique inns, and historic guest houses that offer a quieter, more local alternative to large hotel stays.
Many Key West bed and breakfasts are set inside renovated Victorian, cigar-maker, conch-style, or historic Old Town homes, giving each property its own character, layout, and atmosphere. Visitors can look for romantic rooms, private balconies, courtyard gardens, breakfast service, pool areas, adults-only settings, pet-friendly options, and convenient locations near the island’s most popular attractions.
Use the listings below to explore Key West bed and breakfasts by style, location, amenities, and guest experience. For current room options, rates, and direct reservations, use the Reserve a Room button on each listing.
Almond Tree Inn
Almond Tree Inn Key West sets an elevated standard for adult-only luxury accommodations in the vibrant Old Town district, offering a serene retreat designed for travelers seeking comfort, style, and r...
Ambrosia Key West
Ambrosia Key West delivers a tranquil island retreat surrounded by the vibrant culture of the Old Town Historic District. This tropical Key West resort features an appealing variety of accommodations,...
Andrew’s Inn - Boutique Guesthouse in Old Town Key West
Andrew’s Inn offers a charming boutique guesthouse experience in the heart of Old Town Key West, tucked along quiet Eanes Lane just steps from Duval Street and near the Ernest Hemingway Home and Museu...
Authors Key West Guesthouse - Historic Key West B&B
Authors Key West Guesthouse offers a charming literary-inspired bed and breakfast experience on White Street in Key West, blending historic Conch-style character with a relaxed tropical setting. Desig...
Avalon Bed and Breakfast
Avalon Bed and Breakfast offers an adults-only Key West guesthouse experience on the quieter southern end of Duval Street, blending the charm of a restored historic property with access to the larger ...
Azul Key West
Azul Key West Historic Hotel presents an idyllic adults-only retreat set within one of Key West’s most distinguished Victorian-era mansions, crafted in 1899 by expert shipwrights for a notable cigar b...
Caribbean House - Authentic Key West B&B in Bahama Village
Caribbean House Bed & Breakfast delivers a classic Key West bed and breakfast Bahama Village experience at one of the island’s most culturally rich addresses: 226 Petronia Street. This intimate, t...
Coco Plum Inn Key West - Historic Old Town Hotel
Coco Plum Inn Key West offers a historic Old Town lodging experience in two restored Victorian houses on Whitehead Street, just one block from Duval Street and a short walk from the Hemingway Home, Ke...
Cornish Suite Key West - Historic Adults-Only 2BR Retreat at the Inn on Flemming
The Cornish Suite at Inn on Fleming stands as the premier third-floor sanctuary within this restored 1894 Key West mansion, offering sophisticated comfort for adults seeking elevated island tranquilit...