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Featured Florida Keys Historic Hotels

See all 1,047 Hotels in Florida Keys
Southernmost House

Southernmost House

1400 Duval Street, Key West
3.5 out of 5.0
4.5 out of 5 (653 reviews)
rented a bike in Islamorada and rode down; locked up the bike in the front yard for pick up. Then,had a beautiful room overlooking the water, and was a few blocks from Fantasy Fest. Ideal.
  29 Oct 2017

£181

£181
Heron House - Adult Only

Heron House - Adult Only

512 Simonton St, Key West
3.5 out of 5.0
4.3 out of 5 (1,519 reviews)
Beautiful and great price!We've stayed at several places around Old Town Key West, and this was definitely the most beautiful, with the most convenient location, at the best price!
  8 Jan 2018

£116

£116
Heron House Court - Adult Only

Heron House Court - Adult Only

412 Frances St, Key West
3.5 out of 5.0
4.4 out of 5 (1,361 reviews)
Lovely guest house with super friendly staffI usually prefer larger hotels, but in Key West guesthouses are the more common & more affordable way to visit. It was a typical & lovely Key West B & B experience with an excellent small pool & a luxurious hot tub. The room was small & there was shower only, no bath (at least in my room). The lobby ...
  14 Jan 2018

£101

£101
Albury Court Hotel - Key West

Albury Court Hotel - Key West

1030 Eaton St, Key West
3.5 out of 5.0
4.0 out of 5 (1,473 reviews)
Great place to stay! Close to Half Marathon!Visiting Key West to participate in the 20th Annual Key West Half Marathon, and this delightful place did not disappoint! Within walking distance to several of our favorite locations, and especially close to the Half Marathon start, finish & after party activities. Albury Court also provided a very ...
  18 Jan 2018

£143

£143
The Marker Waterfront Resort Key West

The Marker Waterfront Resort Key West

200 William Street, Key West
4.5 out of 5.0
4.5 out of 5 (872 reviews)
Noise lot of walking noise over head all the time love the place but did not like paying to park in there building all the staff was great
  15 Jan 2018

£179

£179
The Marquesa Hotel

The Marquesa Hotel

600 Fleming Street, Key West
3.5 out of 5.0
4.9 out of 5 (189 reviews)
Beautiful Environment, Good workout on the StairsLovely appointments, very pleasant staff, Great restaurant is attached. Attractive garden setting, orchids abound. Walk to everything "downtown". Only negative can be the noise level of busy streets on 2 sides.
  11 Jan 2018

£264

£264
Cypress House Hotel in Key West - Adults Only

Cypress House Hotel in Key West - Adults Only

601 Caroline St, Key West
3.5 out of 5.0
4.5 out of 5 (250 reviews)
PerfectI have been staying in key west over the Christmas holiday for 15 years and this last trip we ended up not knowing if we could make it due to an illness. Once we knew we could make this trip all the other places I stayed were already booked. Staying in many different places we all know they really ...
  4 Jan 2018

£190

£190
Merlin Guest House - Key West

Merlin Guest House - Key West

811 Simonton Street, Key West
2.5 out of 5.0
4.4 out of 5 (249 reviews)
very convenient to all activities.weather was cold and damp during our four day stay and there is no facility to have breakfast indoors. Hence no breakfast for our entire stay.
  10 Jan 2018

£164

£164
Duval House

Duval House

815 Duval St, Key West
3.5 out of 5.0
4.2 out of 5 (684 reviews)
Great location Great location. Pool was great, breakfast was nice and the property was beautiful
  9 Jan 2018

£135

£135
Casa Marina, A Waldorf Astoria Resort

Casa Marina, A Waldorf Astoria Resort

1500 Reynolds Street, Key West
4.5 out of 5.0
4.2 out of 5 (2,166 reviews)
Great Location in Key West This was our the 2 ND attempt to come to Key West . We were cancelled after Hurricane Irma , and then delayed 1 day by the super snow storm to hit the East Coast . Upon Check in Ryan at the front desk upgraded our room for the inconvenience . That was a great start . 2 days later we were called to ...
  11 Jan 2018

£218

£218
Map

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Pocket Guide: Historic Hotels Hotels in Florida Keys

Find a Historic Hotel in the Florida Keys

With their fair share of monuments and museums, the islands of the Florida Keys are rich with historical attractions. But check into a historic hotel in the Florida Keys and you can experience a slice of its history first-hand. Whether it’s a grand hotel of yesteryear or a converted historical building, you can check into these live-in antiques all over the Florida Keys.

Hotels in Historic Florida Keys Buildings

From Victorian inns to 19th-century mansions decked out with chandeliers, historic hotels in the Florida Keys come in many forms, but they’ve usually been updated for the modern traveller with the WiFi and air conditioning.

The most recognisable historic hotels are probably the simple Conch houses of Key West. Originally built in the 19th century, these buildings dominate the island’s architectural landscape and many have been converted into guesthouses.

Each aspect of these wooden structures, such as their shutters, roof hatches and wide verandas were designed with the hot climate in mind. The earliest of these are simple in design, but the facades became more elaborate as the trend for decorative elements grew in popularity.

Historic Attractions in Florida Keys

From pirates to literary legends, many of Key West’s former inhabitants have left their mark on the islands. There are historical hotels and attractions from all eras with stories to tell. Crane Point Museum, Nature Centre and Historic Site in Marathon, which promotes the heritage of the Florida Keys, and the quirky, must-visit History of Diving Museum in Islamorada are two of the best.

But most of the must-see historical sites can be found in Key West. It’s a tiny island, so wherever your historic hotel is, you won’t have to travel far to visit heritage sites and museums like the Harry S. Truman Little White House, the Key West Art and History Museum and the Key West Shipwreck Museum.

One of the most popular of the island’s literary landmarks is the Hemingway House and Museum, the Spanish colonial building in which the author Ernest Hemingway lived and wrote some of his finest works.