Florida Keys is a popular travel destination for local charm, sunny weather, and pretty beaches. For those wanting a particularly quaint experience, there are several hotels and inns located in historic buildings — some even frequented by President Harry Truman and Ernest Hemingway. We visited the area’s top hotels to evaluate how every feature stacks up against the competition, from the rooms to the pools to the restaurants. So if you’re planning a getaway and need a place to start, you’ve come to the right place. Take a look at the best historic hotels in the Florida Keys and get inspired!

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The Weatherstation Inn

Key West, Florida, United States

This charming, 8-room property is housed in a historic building on a quiet street in Old Town Key West, within walking distance to some of the major tourist attractions, and to a couple of good beaches. Each of its rooms has a distinct character and few amenities (a flat-screen TV and little more), but they come with charming decor (four-poster beds, antique touches) and relaxing views of the well-tended grounds. The hotel has no amenities whatsoever -- just a tiny pool -- but there are some great freebies like free Wi-Fi, free parking, and a free quality continental breakfast.


Marquesa Hotel

Key West, Florida, United States

Refurbished from 1884 conch houses, the Marquesa Hotel is a compound of four buildings surrounding lovely interior gardens and two pools. A narrow staircase off the lobby leads to the individually decorated rooms. Light and airy rooms feature flat-screen TVs, mini-fridges, and cozy sitting areas with ottomans. Bathrooms are basic and clean with shower/tub combos and marble sinks. Suites have private terraces with cute wicker furniture and some are adjacent to one of the hotel's pools. An appealing on-site restaurant, Cafe Marquesa, serves fresh local seafood. No children under 14 are allowed at the hotel, providing this property with a distinctly romantic feel. Free Wi-Fi and parking add value, and the Old Town location two blocks from Duval Street is convenient.


The Conch House Heritage Inn

Key West, Florida, United States

The 10-room Conch House Heritage Inn is an historic, competitively priced retreat in Old Town Key West in walking distance to Duval Street. This charming, mid-range property draws repeat guests with its warm hospitality, free homemade breakfast, daily happy hour, and tropically landscaped outdoor pool area. Guest rooms are individually decorated with antiques, and have mini-fridges and flat-screen TVs; the suite offers a full kitchen. The unheated pool, though, can be a bit chilly for comfort. Note that kids under age 12 aren't allowed. Another option may be The Mermaid & The Alligator Bed & Breakfast, which has a heated pool. 


La Mer Hotel and Dewey House at Southernmost Beach Resort

The 19-room La Mer Hotel and Dewey House is an upscale, adults-only property built at the turn of the century on South Beach. With its breezy yet elegant style, beachfront dining terrace, and access to a sister hotels' pools, spa, and three bars, this property offers the features of a resort with a bed-and-breakfast atmosphere. Guest rooms are beautifully decorated in a classic style, and have flat-screen TVs, mini-fridges, and coffeemakers; some open to balconies. The property serves free breakfast, along with occasional treats like chocolate-covered strawberries, but there's a pesky resort fee and minimum stays are occasionally required. For a more exclusive resort-style vacation, guests may want to consider the Ocean Key Resort and Spa.


The Southernmost House

Key West, Florida, United States

The Southernmost House is an adult-only property in an historic Victorian home directly on the ocean and just off popular Duval Street. This 18-room, mid-range inn feels sophisticated but laid-back, and has hosted the likes of Hemingway and Capote. Its genteel sitting porches, antique furnishings, and original Tiffany-glass entrance canopy connect visitors with old Key West, while the spacious, individually designed guest rooms offer modern comforts, such as flat-screen TVs and mini-fridges. Free breakfast is served daily, and there's a lovely zero-edge pool overlooking the ocean. Noise from Duval Street can infiltrate some rooms, and service is not always as personalized as some might expect from a bed-and-breakfast.


Old Town Manor

Key West, Florida, United States

The 14-room, mid-range Old Town Manor is an adult-only bed-and-breakfast set in an historic Victorian mansion, just a block from Key West's popular Duval Street. The two-house Manor is cozy and warm with tons of character, including a grand front porch with rocking chairs, and lush gardens where guests can sit and relax. The ample free breakfast includes organic fruits and baked goods, and pets are enthusiastically welcomed. Guest rooms are large and individually decorated, with beautiful modern bathrooms and free Wi-Fi. In an area filled with guesthouses, the Old Town's quiet charm and attention to detail raise it above the rest. 


Eden House

Key West, Florida, United States

Eden House has had the same owner for nearly 40 years, and numerous loyal customers return year after year for the affordable prices and friendly vibe. Rooms can be bare-bones, especially the semi-private ones with shared bathrooms and no TVs or mini-fridges. Even the higher-level rooms are fairly plain, though, with small bathrooms, simple (verging on bland) decor, and very little furniture (aside from the apartment-style rooms). This historic hotel does have a nice pool courtyard surrounded by palm trees, lovely grounds with deck areas, hammocks, and koi ponds throughout, and tons of freebies (Wi-Fi, parking, and happy hour) that make it a good value.


The Banyan Resort

Key West, Florida, United States

Key West is a place that's steeped in history, and the Banyan Resort is no exception: Its nine buildings are on the National Register of Historic Places. The 38 suites are clean and bright, but quality varies drastically. Most have dated, uninspired decor, with tube TVs, floral print sofas, and tacky lighting. But each suite has patios, balconies, and kitchens; the grounds are lush; and there are two shady (if small) outdoor pools. The hotel's biggest draw is its location just steps some of Key West's premier attractions, such as happening Duval Street and Mallory Square.


Knowles House B&B

Key West, Florida, United States

The Knowles House B&B is an historic conch house near Duval Street and the waterfront with eight individually decorated guest rooms. This charming, mid-range property serves homemade breakfast on a tropical patio, and offers a tiny outdoor pool, hot tub, and rooftop sun deck. Guest rooms have TVs, mini-fridges, and antique touches; one has a whirlpool tub. Daily happy hour includes free wine and beer, and guests can help themselves to free coffee and baked goods throughout the day and night. Some rooms have dated decor and tube TVs, however. 


Artist House

Key West, Florida, United States

Some guests might steer clear of the home of the haunted stuffed doll that inspired the movie "Chuckie," but Artist House, one of the most photographed houses in Key West, is immaculate, bright, colorful, and welcoming, with nothing spooky about it. This restored Victorian mansion serves European pastries at breakfast and hosts a free daily happy hour. It's located within a few minutes' walk of Duval Street and the heartbeat of Key West.


Cypress House Hotel : Key West

Key West, Florida, United States

One of the six properties included in Historic Key West Inns, the tastefully renovated and mid-range Cypress House, on a quiet corner in old town, has 22 spacious rooms, and a comfortable outdoor pool area. It's a block from Duval Street, the seaport, and Key West’s many shops, restaurants, and bars. Free margaritas are served at a daily happy hour and breakfast is included in the rate. The historic hotel does not permit children.


Angelina Guest House

Key West, Florida, United States

The Angelina Guest House is a former 1920s bordello and gambling den turned into a charming Key West bed-and-breakfast teeming with Southern hospitality. The 13-room budget property welcomes adults only, and maintains a quiet, peaceful atmosphere; the owners request that guests leave their partying on nearby Duval Street. The Angelina offers a lovely lagoon-style pool, bike rentals, and homemade cinnamon rolls included in the free breakfast. Accommodations are clean and well cared for, ranging from simple rooms with shared bathrooms to efficiencies with refrigerators and microwaves; guest rooms don’t have phones, and only one has a TV.