Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Search 321,000 hotels worldwide.

Get the best price available for your trip.

No Expedia cancellation fee to change or cancel almost any hotel reservation.


Featured Florida Keys Historic Hotels

See all 508 Hotels in Florida Keys
Island City House Hotel

Island City House Hotel

411 William Street, Key West
3.0 out of 5.0
4.6 out of 5 (311 reviews)
Wonderful The staff is wonderful, great location, beautiful grounds and the rooms are clean. This is our favorite hotel in Key West, we stay here about six times a year and love it!!
  27 Aug 2017
Albury Court Hotel - Key West

Albury Court Hotel - Key West

1030 Eaton St, Key West
3.0 out of 5.0
4.0 out of 5 (1,521 reviews)
PerfectRooms were ready. Clean. Nice and cool. Beds were incredibly comfortable. Pool and breakfast area were fine. Check in took a few minutes but in Key West..one shouldn't be in a rush anyway. Parking is a bit of a puzzle but can't blame hotel for that. Would recommend and would (Likely will) return ...
  9 Nov 2017

£118

£118
The Marker Waterfront Resort Key West

The Marker Waterfront Resort Key West

200 William Street, Key West
4.0 out of 5.0
4.6 out of 5 (827 reviews)
Great location.Easy walking distance to many restaurants, attractions and waterfront.
  17 Nov 2017

£134

£134
The Southernmost Inn-Adults Only

The Southernmost Inn-Adults Only

525 United Street, Key West
2.5 out of 5.0
4.1 out of 5 (832 reviews)
We were put on the “3rd floor” the ceiling slants over the bedroom. If you are taller than 5’ you can’t stand up. We laughed about it but if you are on extended stay you may want to request alternative accommodations.
  14 Nov 2017

£112

£112
Lighthouse Court Hotel - Key West

Lighthouse Court Hotel - Key West

902 Whitehead St, Key West
3.5 out of 5.0
4.1 out of 5 (894 reviews)
We spent 2 nights here before we were evacuated due to hurricane Irma. The hotel is very nice and in a good location. The staff are outstanding.
  10 Sep 2017

£135

£135
Heron House - Adult Only

Heron House - Adult Only

512 Simonton St, Key West
3.5 out of 5.0
4.3 out of 5 (1,485 reviews)
Great spot.Heron House was a wonderful place. Lovely old historic building, spacious accommodations, helpful and professional staff. Would recommend to anybody wanting a great place to stay while in Key West.
  15 Nov 2017

£91

£91
La Concha Hotel & Spa

La Concha Hotel & Spa

430 Duval St, Key West
4.0 out of 5.0
4.1 out of 5 (1,859 reviews)
Top notch StaffThe hotel common areas and staff are very good and helpful. I stopped to ask a question or two several times and always received accurate information. While coming and going they front desk staff always had a hello and a smile which makes me feel like a valued customer. The remodeled lobby/bar is ...
  5 Nov 2017

£147

£147
Silver Palms Inn

Silver Palms Inn

830 Truman Ave, Key West
3.5 out of 5.0
4.4 out of 5 (2,449 reviews)
Night in keysClean friendly staff. Comfortable room would definitely stay there again
  18 Nov 2017

£137

£137
Southernmost House

Southernmost House

1400 Duval Street, Key West
3.0 out of 5.0
4.5 out of 5 (648 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

£187

£187
Eden House

Eden House

1015 Fleming St, Key West
3.5 out of 5.0
4.5 out of 5 (682 reviews)
Great EnvironmentThis was our 4th stay. The staff is awesome and the property is so welcoming. Each room is well appointed.
  18 Nov 2017

£140

£140
Map

Recently booked Florida Keys hotels

Courtyard by Marriott Key Largo
3.0 out of 5.0
Last booking: 11 minutes ago
Best Western Key Ambassador Resort Inn
2.5 out of 5.0
Last booking: 20 minutes ago
Artist House on Fleming
3.5 out of 5.0
Last booking: 35 minutes ago
Casa Morada
3.5 out of 5.0
Last booking: 45 minutes ago
24 North Hotel Key West
3.5 out of 5.0
Last booking: 48 minutes ago
Southernmost Beach Resort
4.0 out of 5.0
Last booking: 1 hour ago
Banana Bay Resort and Marina
2.5 out of 5.0
Last booking: 1 hour ago
Ibis Bay Beach Resort
2.5 out of 5.0
Last booking: 1 hour ago
Mangrove Marina and Resort Aqualodge Houseboats
3.0 out of 5.0
Last booking: 1 hour ago

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.