1. The Southernmost Inn
Location: 525 United St (Simonton Street), Key West, FL 33040. TheSouthermostInn.com
Historic credentials: Housed in a restored 1800s cigar factory.
Features: 38 guest rooms, neo-colonial design, in-suite modern comforts (flat-screen TVs, AC, kitchen in some units) + two pools and hot-tub area.
Advantage: Combines historic architecture + boutique scale + modern amenities, in a quieter part of Old Town yet close enough to everything.
2. The Conch House Heritage Inn
Location: 625 Truman Ave, Key West, FL 33040. +8 rooms…
Historic credentials: One of the island’s pioneer estates, Victorian architecture with Bahamian influences (wrap-around porches, tin roof, gingerbread trim) and still operated by descendants of original owners. ConchHouse.com
Features: Tranquil garden/pool setting, short walk to Duval Street, Hemingway House museum etc.
Advantage: Offers rich sense of place (historic home + tropical setting) with fewer rooms, making it more intimate than big resorts.
Advantages of historic inns vs. larger resorts / standard hotels
Here are some of the key benefits of choosing a historic inn in Key West:
Character & sense of place: Historic inns often are housed in restored buildings with original architectural features (wood floors, porches, decorative trim) that reflect Key West’s heritage. Staying there gives you more of a “local story” than a standardized hotel tower.
Smaller scale / more personal service: With fewer rooms, you typically get more personalized attention, quieter ambiance, and a more relaxed pace — fewer crowds, fewer masses of guests moving in/out.
Prime walkable locations in Old Town: Many historic inns are located in the heart of Old Town Key West, making it easy to walk to dining, bars, sights — often better than some resorts that are on the outskirts or more spread out.
Uniqueness in design & rooms: Each room may be different, built within the context of the historic structure, so you often get more uniqueness than a cookie-cutter hotel room.
Often more tranquil / boutique-feel: For travelers seeking a quieter getaway, rather than a big resort with large crowds, historic inns can deliver a more peaceful, charming stay.
What to watch / trade-offs
Historic inns might have fewer amenities compared to large resorts but if amenities aren’t your thing, then other fun options exist…
Room size/bathrooms may be more modest compared to brand-new builds but that may add to the charm.
Because they’re in historic buildings, sometimes quirks like narrower stairs or older fixtures may exist.
Pricing can still be high because of the desirable location and character. Keep in mind that Key West is small, 2x4 miles.