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.