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Browse for Key West Historic Hotels from $99

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Top Key West Historic Hotels

The Marquesa Hotel
3.5 out of 5
600 Fleming Street, Key West, FL
The price is $250 per night
4.8/5Exceptional! (392 reviews)

"A beautiful property in a great location. The back of the property is your own private oasis with lush vegetation and 2 beautiful swimming pools. Downtown location with spa/resort feel. Exceeded my expectation. Cafe Marquesa is excellent"…"

Reviewed on Jun 29, 2020

The Marquesa Hotel
Weatherstation Inn
2.5 out of 5
57 Front St, Key West, FL
Free CancellationReserve now, pay when you stay
The price is $151 per night
4.7/5Exceptional! (540 reviews)

"This place was so much better than I could have expected. I booked based up yoon"…"

Reviewed on Jul 3, 2020

Weatherstation Inn
Island City House Hotel
3 out of 5
411 William Street, Key West, FL
The price is $162 per night
4.7/5Exceptional! (564 reviews)

"I wish the pool had been a little cleaner. Lots of tree stuff from all the trees overhead. The pool tiles need cleaned."…"

Reviewed on Jun 27, 2020

Island City House Hotel
Ambrosia Key West
3.5 out of 5
622 Fleming St, Key West, FL
The price is $155 per night
4.6/5Exceptional! (417 reviews)

"Great guest house! Took great care to ensure a safe stay."…"

Reviewed on Jul 6, 2020

Ambrosia Key West
Downtown Cottage in Historic District
4.6/5Wonderful! (54 reviews)
All Good

"This was a perfect fit for a family of four with two boys (5) (1). We did rent a crib from a third party but that was a breeze. The pool is shared with two other units, but it’s a large pool for key west with a shallow and deep end. The oversized porch in the back was perfect for when the boys went ..."…"

Reviewed on Jun 28, 2020

Downtown Cottage in Historic District
Duval House
3 out of 5
815 Duval St, Key West, FL
The price is $105 per night
4.6/5Wonderful! (698 reviews)

"Very well maintained property with excellent staff who are very courteous and prime location right in the middle of everything"…"

Reviewed on Jul 2, 2020

Duval House
Silver Palms Inn
3.5 out of 5
830 Truman Ave, Key West, FL
Free CancellationReserve now, pay when you stay
The price is $129 per night
4.6/5Wonderful! (1,016 reviews)

"Very friendly and helpful desk staff. Room was very clean and amenities quite nice (Bath & Body Works Aromatherapy shampoo/conditioner, soap and lotion!). Hotel is located about 5-6 blocks from Duvall Street (an easy walk!). Nice pool deck area. Hotel did serve breakfast, but adjusted their procedure ..."…"

Reviewed on Jul 10, 2020

Silver Palms Inn
Kimpton Ridley House
3 out of 5
601 Caroline St, Key West, FL
Free Cancellation
The price is $205 per night
4.5/5Wonderful! (475 reviews)

"The property was beautiful and near everything. The pools were outstanding. Our room was quite small. Lovely. but small."…"

Reviewed on Mar 22, 2020

Kimpton Ridley House
Southernmost House
3 out of 5
1400 Duval Street, Key West, FL
Free CancellationReserve now, pay when you stay
The price is $265 per night
4.5/5Wonderful! (846 reviews)

"Great location and beautiful view. We had a wonderful stay."…"

Reviewed on Mar 27, 2020

Southernmost House
Heron House Court - Adult Only
3 out of 5
412 Frances St, Key West, FL
The price is $104 per night
4.5/5Wonderful! (995 reviews)
Great staff and location. Roman is fantastic.

"Great staff and location. Roman is the best"…"

Reviewed on Jul 7, 2020

Heron House Court - Adult Only
Kimpton Ella's Cottages
2.5 out of 5
811 Simonton Street, Key West, FL
Get Rates
4.5/5Wonderful! (415 reviews)

"The property has been nicely upgraded. The location to downtown Duval Street is perfect."…"

Reviewed on Mar 16, 2020

Kimpton Ella's Cottages
The Marker Key West Harbor Resort
4 out of 5
200 William Street, Key West, FL
Free CancellationReserve now, pay when you stay
The price is $233 per night
4.4/5Wonderful! (993 reviews)

"Nice location, cleaned and friendly. We stayed for one night, we regretted not being able to stay longer."…"

Reviewed on Jul 2, 2020

The Marker Key West Harbor Resort
Heron House - Adult Only
3.5 out of 5
512 Simonton St, Key West, FL
The price is $113 per night
4.3/5Excellent! (999 reviews)

"Lovely secluded pool! Nice patio set up, very quiet and relaxing."…"

Reviewed on Jul 10, 2020

Heron House - Adult Only
Southernmost Beach Resort
4 out of 5
1319 Duval Street, Key West, FL
Free CancellationReserve now, pay when you stay
The price is $229 per night
4.2/5Excellent! (2,571 reviews)

"Great location, beautiful views, and comfortable accommodations. Easy to walk to many points of interest in Key West. Parking available onsite, although you need to pay a daily rate."…"

Reviewed on Jul 10, 2020

Southernmost Beach Resort
The Southernmost Inn-Adults Only
2.5 out of 5
525 United Street, Key West, FL
Free CancellationReserve now, pay when you stay
The price is $99 per night
4.2/5Very Good! (997 reviews)

"I liked the decor and the pool set up. I didnt understand why it was adults only. The room was kinda cramped in regards to the set up. Some extra towels wouldve been nice"…"

Reviewed on Jul 8, 2020

The Southernmost Inn-Adults Only
Kimpton Fitch Lodge
3 out of 5
1030 Eaton St, Key West, FL
The price is $165 per night
4.1/5Very Good! (998 reviews)

"We actually stayed at Chelsey House since Albury is under renovations. Beautiful property, nice staff, very accommodating. Just need to update staff not to enter rooms when do not disturb sign is on door."…"

Reviewed on Jan 22, 2020

Kimpton Fitch Lodge
Crowne Plaza Key West-La Concha
4 out of 5
430 Duval St, Key West, FL
Free Cancellation
The price is $151 per night
4.1/5Very Good! (1,012 reviews)

"Convenient clean, beautiful rooms & nice pool, close to everything."…"

Reviewed on Jul 11, 2020

Crowne Plaza Key West-La Concha
Casa Marina Key West, A Waldorf Astoria Resort
4 out of 5
1500 Reynolds Street, Key West, FL
Free CancellationReserve now, pay when you stay
The price is $230 per night
3.7/5Good! (996 reviews)

"I didn't like the outside elevators. They were not upkept at all. I loved that there was an adult only pool since this was an adult only trip."…"

Reviewed on Jul 11, 2020

Casa Marina Key West, A Waldorf Astoria Resort
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Your Guide to Historic Hotels in Key West

When you take a Key West trip out of town, it is easy to decide on a chain you are familiar with, or a modern hotel. You may be used to your room having all the familiar amenities. But sometimes opting to stay in a more unique hotel can elevate your holiday. A stay in a Key West historic hotel still offers you with a well-appointed room that is also teeming with personality. Furthermore, it allows you to immerse yourself in Key West's history.

Old-World Charm, New World Amenities

As soon as you walk through the reception area of your Key West hotel, you'll be whisked back in time. With their old-world charm and marvelous back stories, you'll love how these historic hotels stand apart from their modern counterparts. Although these accommodations may be older, they have most of the up-to-date comforts that allow you to keep in touch or relax on your vacation. You will find your room outfitted with a comfortable bed, and just about anything else you'll need for a wonderful stay.

After you've spent time appreciating your hotel, you can tour the art galleries and well-known landmarks to take in more of the area's culture. If you are a history buff, then you picked the right place. Key West has 4 historical buildings and sites in the area. After checking out places like HA. 19 (Japanese Midget Submarine), INGHAM (USCGC), and Ernest Hemingway House you'll be able to pen your own history book on Key West. If you have time, then squeeze in a visit to Fort Zachary Taylor. Looking for more things to do in Key West? You can see what fellow guests found worth a visit in our review section. You'll find 14978 tips in our comment section on more areas to visit, great spots to eat, and what they enjoyed most about their visit.

Your Key West Accommodation Is Waiting

If you want to get the most out of your Key West visit, a stay in one of these vintage hotels will elevate your time spent in this historically-rich city. With Expedia having 830 of these one-of-a-kind hotels to select from. Rates on these Key West historic hotels range from $99 to $265. You are bound to find at a great rate. However, like the past civilizations you're examining, these deals won't last indefinitely. Reserve soon to get your room in one of these historic properties.

Frequently asked questions

What can I expect on my historical trip to Key West?
A visit to the historical places in Key West is likely on top of your travel itinerary. And while you’re here, you can check out the great live music and scenic seaside. You can also discover the area’s lively festivals.
What's the best hotel in Key West to learn about local history?
Based on our travel expertise, Southernmost House is a top 3-star historic hotel bookable on Expedia and it offers free breakfast. Southernmost Point is a short 11-minute walk away. Other choices to soak up the local history include The Marker Key West Harbor Resort and Casa Marina Key West, A Waldorf Astoria Resort.
How many historical hotels will I find in Key West?
In Key West, you’ll find 830 hotels and other accommodations bookable on Expedia, including 107 historic hotels or hotels close to historic sites.
What are the top historical sites and other places in Key West?
Key West is notable for landmarks like Ernest Hemingway Home and Museum, Harry S. Truman Little White House, and Fort Zachary Taylor Historic State Park. Known for its live music and festivals, cultural venues include Key West Shipwreck Museum, Key West Lighthouse and Keeper’s Quarters Museum, and Audubon House and Tropical Gardens. Other popular sights include Duval Street and Mallory Square.
What is a historic hotel like in Key West?
Guests who choose a historic hotel can spend a night or two in a place that has an officially recognized historic designation. A stately home, palace or even a lodge, old police station, or skyscraper can be turned into a historic hotel provided that it has special significance. Traditional architecture and period features are often found within the guestrooms or public spaces of these historic hotels in Key West, bringing the history to life.
What is the difference between a historic hotel and a heritage hotel?
“Heritage hotel” is more common in Asia and Europe, while “historic hotel” is more common in the U.S. though overall the terms are quite similar. The architecture and building of historic hotels tend to be the most important aspect. For a heritage hotel, it’s mainly the cultural value as well as how it shaped the community.
Do historic hotels in Key West have modern facilities?
Hotel interiors feature the modern conveniences and safety features you’ve come to expect, though efforts have been made to preserve the historic aspects and traditions. Private rooms with updated bathroom facilities, free WiFi, and the usual amenities found at a contemporary hotel will also be available in a historic hotel. When you book a historic hotel in Key West, don’t worry that you’ll find a place that’s uncomfortable for guests or simply rundown.

Travelers Loved These Historic Hotels

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