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Featured Florida Keys Historic Hotels

Southernmost House
Southernmost House
3.0 out of 5.0 1400 Duval Street, Key West, FL
Free Cancellation
$322
4.9/5 (16 reviews)

The house was built in 1897 and has vast amount of rich history; from being the mansion of Florida's first millionaire, to a speakeasy where All Capone was almost asassinated, to a favorite vacation spot for many US presidents. Besides the history, it is very relaxing here. The pool is very clean ...

Reviewed on Oct 11, 2019
Guests of Southernmost House enjoy features like an outdoor pool, free WiFi in public areas, and free newspapers. Self parking is offered for USD 20 per night. ...
HistoricalPoolOutdoor Pool
The Marquesa Hotel
The Marquesa Hotel
3.5 out of 5.0 600 Fleming Street, Key West, FL
$300
4.9/5 (13 reviews)

Beautiful pools and great room with deck overlooking pools.

Reviewed on Oct 15, 2019
Awarded Conde Nast Top 100 List status in 2015, The Marquesa Hotel features 2 outdoor pools, free WiFi in public areas, and a 24-hour business center. If you ...
HistoricalParkingGardens
Cypress House Hotel in Key West - Adults Only
Cypress House Hotel in Key West - Adults Only
3.0 out of 5.0 601 Caroline St, Key West, FL
$165
4.9/5 (11 reviews)

Great location, clean and comfortable. Friendly staff.

Reviewed on Aug 15, 2019
Cypress House Hotel features an outdoor pool, free WiFi in public areas, and coffee in a common area. Self parking is available for USD 30 per night. Front-desk ...
HistoricalParkingBreakfast
Island City House Hotel
Island City House Hotel
3.0 out of 5.0 411 William Street, Key West, FL
$197
4.8/5 (22 reviews)

Nice property with a pool and comfy rooms(more like suites). There is no on-site parking, but that's Key West for you.

Reviewed on Oct 8, 2019
Guests staying at Island City House Hotel enjoy an outdoor pool, a sauna, and a rooftop terrace. Free offsite parking is available if you drive. Helpful staff ...
HistoricalGardensBiking
Heron House Court - Adult Only
Heron House Court - Adult Only
3.0 out of 5.0 412 Frances St, Key West, FL
$129
4.7/5 (69 reviews)

Staff is great! Proximity to many things, Rooms are clean and cozy. Front porch has a nice breeze. Like the upstairs a lot.

Reviewed on Oct 4, 2019
At Heron House Court - Adult Only, guests have access to an outdoor pool, a rooftop terrace, and free WiFi in public areas. The front desk has multilingual staff ...
HistoricalRecreationBreakfast
Merlin Guest House - Key West
Merlin Guest House - Key West
2.5 out of 5.0 811 Simonton Street, Key West, FL
Free Cancellation
$195
4.7/5 (9 reviews)

Staff was really welcoming and room was big and clean.

Reviewed on Aug 27, 2019
Guests of The Merlin Guest House enjoy features like an outdoor pool, free WiFi in public areas, and free newspapers. Self parking is offered for USD 20.00 per ...
HistoricalGardensParking
Duval House
Duval House
3.0 out of 5.0 815 Duval St, Key West, FL
$138
4.6/5 (29 reviews)

Right on Duval near all the action. Beautiful grounds loved the room. Bed was a bit uncomfortable and small shower otherwise perfect. Excellant breakfast

Reviewed on Aug 8, 2019
Guests of Duval House enjoy an outdoor pool, free WiFi in public areas, and microwave in a common area. Self parking is available for USD 20 per night. The front ...
HistoricalGardensParking
Heron House - Adult Only
Heron House - Adult Only
3.5 out of 5.0 512 Simonton St, Key West, FL
4.5/5 (42 reviews)

this was our third time staying at the Heron House and each time the accommodations and staff are outstanding! The rooms are clean and the location is excellent-I would highly recommend staying at the Heron House!

Reviewed on Jul 15, 2019
At Heron House - Adult Only, guests have access to an outdoor pool, a rooftop terrace, and free WiFi in public areas. Front-desk staff can assist with concierge ...
HistoricalAir ConditioningInternet
Casa Marina, A Waldorf Astoria Resort
Casa Marina, A Waldorf Astoria Resort
4.0 out of 5.0 1500 Reynolds Street, Key West, FL
$280
4.1/5 (269 reviews)

I have stayed her twice. I love the convenience to anything you want to do un Key West.

Reviewed on Aug 20, 2019
A local mainstay since 1920, Casa Marina, A Waldorf Astoria Resort offers a full-service spa, 2 outdoor pools, and a health club. Valet parking is offered for ...
HistoricalDiningBiking

Uncover the Intrigue of a Florida Keys Historic Hotel

Featuring a variety of historic hotels, Florida Keys offers travelers a rich tapestry of one-of-a-kind local experiences. Whether you choose opulence or rustic charm, you can embrace life in a different era for a night, a weekend, or an extended stay.

Upgrades and restores
Historic hotels have often been painstakingly restored to reflect their original glory or to update them with a contemporary vibe. You can choose to rough it in humble historic accommodations, or experience the good life in the area's sophisticated restored mansions and original hotels.

Historic hotels allow you to embrace each hotel’s heyday. Sip drinks in a retro bar, relish a candlelit dinner in a lavish dining room, or enjoy a private fire in your own well-appointed suite.

Many historic hotels even feature original grand facades and modern interiors with newly renovated lobbies and rooms. Others have been meticulously restored to reflect every historic detail of the building’s past. Choose how you wish to experience the history of Florida Keys!

Get a glimpse of the past at a Florida Keys historic hotel
Whether you’re looking for a retro experience or you want something from a different century, a stay at a famous hotel in Florida Keys offers an unforgettable escape that will take your vacation to a new and unexpected level.

Discover life in Florida Keys from a different perspective with a trip back in time and book your historic hotel stay today.

Recent Historic Hotels Reviews

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.