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Check availability on Key West Historic Hotels

Tonight
13 Oct - 14 Oct
Tomorrow
14 Oct - 15 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Key West historic hotels

A balcony with a view of a street, a bench, and a potted plant.
A multi-story building with a ground-level commercial space featuring a brightly lit storefront.
A reception desk with clocks, a Pegasus International Hotel sign, and a computer monitor.
A hotel lobby with a bar area, seating, and a fireplace.

1. Pegasus International Hotel

Pegasus International Hotel
Old Town Key West
United States
Karla
£150
includes taxes & fees
14 Oct - 15 Oct
Pegasus International Hotel
A wooden boardwalk leading to a beach with palm trees and a clear sky.
An outdoor patio with wicker furniture and a ceiling fan, surrounded by lush greenery and a view of a residential area.
A large white building with a balcony, palm trees, and a brick pathway leading to the entrance.
A grand room with a large wooden door, a fireplace with a mantelpiece, and a chandelier.

2. Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn
Key West Historic District
United States
chris
£225
includes taxes & fees
15 Oct - 16 Oct
Amsterdam's Curry Mansion Inn
A living room with two sofas, a coffee table, and a window with blinds.
A wooden staircase with a view of greenery outside.
A covered outdoor deck with wicker furniture and a white railing.
A pool area with lounge chairs, a pool with clear blue water, and a covered patio with outdoor seating.

3. CORTEZ ~ Adults Only, 2nd Floor King Room w/Pool View at Azul Mansion!

CORTEZ ~ Adults Only, 2nd Floor King Room w/Pool View at Azul Mansion!
Old Town Key West
United States
Cindy D.
£218
includes taxes & fees
19 Oct - 20 Oct
CORTEZ ~ Adults Only, 2nd Floor King Room w/Pool View at Azul Mansion!
A bedroom with a large bed, a wooden headboard, a desk with a chair, a mirror, and a view of the kitchen and bathroom.
Two orange armchairs with decorative pillows, a round coffee table with books, and a lamp.
A well-lit bedroom with a large bed, a desk, a chair, and a sofa. There are multiple pillows, a lamp, and a plant on the bedside table.
A compact kitchen with a microwave, oven, and sink. There is a small dining table with a bowl and a chair. The kitchen has light blue tiles and wooden cabinets.

4. Studio Blu - Historic Key West Studio + Bikes

Studio Blu - Historic Key West Studio + Bikes
Old Town Key West
United States
Emily F.
£313
includes taxes & fees
26 Oct - 27 Oct
Studio Blu - Historic Key West Studio + Bikes
A beach with people sunbathing and swimming, a clear blue sky, and a calm sea.
A covered porch with white railings and wicker furniture.
A compact kitchen with a microwave, refrigerator, and a sink.
A clear blue swimming pool with lane dividers, a fenced deck area, and a view of the ocean in the background.

5. OLD TOWN STEPS TO DUVAL! LA DOLCE VITA SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST

OLD TOWN STEPS TO DUVAL! LA DOLCE VITA SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST
Old Town Key West
United States
Michael R.
£378
includes taxes & fees
9 Nov - 10 Nov
OLD TOWN STEPS TO DUVAL! LA DOLCE VITA SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST
A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.
A two-story house with a front porch, a staircase, and a garage.
A bar with a signboard listing various destinations.
A pathway through a lush garden with various plants and trees.

6. Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS

Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
Stock Island
United States
Linda
£397
includes taxes & fees
19 Oct - 20 Oct
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
A person swimming with a large, spiky, orange object.
A beach with clear water and gentle waves.
A wooden-paneled room with a bed, a television mounted on the wall, and a door leading to another room.
A yellow building with a balcony, parked cars, and palm trees.

7. Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!

Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!
Old Town Key West
United States
Kayleigh V.
£470
includes taxes & fees
27 Oct - 28 Oct
Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!
A two-story house with a swimming pool, outdoor seating, and a balcony with a yellow umbrella.
A property named Villas Key West with a covered entrance, a white picket fence, and lush greenery.
A room with a bed, a dining table, and a kitchen area.
An open door to a room with a bed, a heart-shaped pillow, and a painting on the wall.

8. Poolside Studio Villa Steps from Duval!

Poolside Studio Villa Steps from Duval!
Old Town Key West
United States
Benjamin K.
£316
includes taxes & fees
15 Oct - 16 Oct
Poolside Studio Villa Steps from Duval!
A two-story house with a swimming pool, outdoor seating, and a balcony with a yellow umbrella.
A cozy dining area with a wooden table, wicker chairs, and a bowl of fruit. There is a ceiling fan and a colorful wall decoration.
A house with a porch, a table, and a chair.
A property named Villas Key West with a covered entrance, a white picket fence, and lush greenery.

9. Two Bedroom Two Bath Poolside Villa Steps from Duval!

Two Bedroom Two Bath Poolside Villa Steps from Duval!
Old Town Key West
United States
Matt S.
£604
includes taxes & fees
29 Oct - 30 Oct
Two Bedroom Two Bath Poolside Villa Steps from Duval!
A spacious living room with large windows, a blue sofa, a green sectional, and a wooden ceiling.
A library with multiple bookshelves filled with books.
A bedroom with a large bed, a desk, and a staircase.
A rooftop deck with a wooden floor, outdoor seating area, and string lights.

10. KAMP - Rooftop Penthouse Overlooking Duval

KAMP - Rooftop Penthouse Overlooking Duval
Old Town Key West
United States
Ward R.
£942
includes taxes & fees
2 Nov - 3 Nov
KAMP - Rooftop Penthouse Overlooking Duval
View all properties

Top Key West Hotel Reviews

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent
"Staff was great"
Robert A 3-night trip
Posted 5 hours ago
DoubleTree Resort by Hilton Grand Key - Key West
Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"Being near the pool was very convenient. There was no A/C in the gym, the walk down the stairs from the balcony to the pool was hazardous. There was no walkway, just rocks. The elevators closest to our apartment was out of order which caused us to walk quite a bit. The floors in the apartment were very dirty. We requested to have them cleaned. They sent someone up while we were gone and they cleaned the apartment however the floors were left untouched. They didn't clean them. We advised the front desk, they apologized but it was never corrected. The shuttle was definitely a plus but get there super early because if there are 12 people before you, you're not going. The pool is beautiful and very clean. The food at the pool side bar was very good. So a lot of plus' but unfortunately some misses. The people at the front desk were always very friendly."
Helena 8-night trip
Posted 9 hours ago
Beachside Resort & Residences
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

8/10 Good
"Le déjeuner, le service de bar et l’accueil était top. L’attitude des femmes de ménage et la propreté des entretiens dans la chambre étaient très ordinaire."
Dominique 4-night trip
Posted 10 hours ago
Winslow's Bungalows - Key West Historic Inns
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

10/10 Excellent
"We loved this resort! We will definitely be returning here in the future. Great location- not far from Duvall St but close enough that it’s only a 10 minute drive."
Vernon 4-night trip
Posted 14 hours ago
Parrot Key Hotel & Villas
Hilton Key West Resort & Marina

Hilton Key West Resort & Marina

10/10 Excellent
"Friendly Staff Nice Place"
Eric A 1-night trip
Posted 17 hours ago
Hilton Key West Resort & Marina
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"We went with 2 other couples 2nd year in a row at Southern Most, that should tell you how much we enjoyed it! Great location, food rooms were always cleaned."
Theresa 5-night trip
Posted 1 day ago
Southernmost Beach Resort and Guesthouses
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

8/10 Good
"Somewhat disappointed. Sink was stopped up on arrival, however it was repaired rather quickly. WiFi was non-existent. Room was very clean and staff was helpful. I would give it a 7 out of 10 for the price. I would stay again."
Barry 3-night trip
Posted 1 day ago
Hilton Garden Inn Key West / The Keys Collection
Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

8/10 Good
"Not applicable."
Nhia 2-night trip
Posted 1 day ago
Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Frequently asked questions

What can a history buff expect from a stay in Key West?
A visit to the sights with historical relevance in Key West is likely first on your sightseeing itinerary. And while you're here, you can check out the great live music and scenic seaside. You can also discover the area's entertainment choices.
Where's the best place to stay in Key West to be near historical sites?
Based on our travel expertise, Amsterdam's Curry Mansion Inn is a top historic guest house bookable on Expedia and it features free Wi-Fi. Harry S. Truman Little White House is a short walk away. Other choices near historic sites include ARIA~Adult Only, Treetop King Suite w/ Balcony & Community Pool! and FLOR DE CANA ~ Adults-Only 2nd Floor Queen Room w/Pool View at Azul Mansion!.
How many historical hotels are there in Key West?
In Key West, you'll find 2618 hotels and other accommodation options bookable on Expedia, including 16 hotels designated as historic or close to historic sites.
What are the most important historical sites and other places in Key West?
Key West is notable for landmarks like Ernest Hemingway Home and Museum, Key West Lighthouse and Keeper's Quarters Museum and Harry S. Truman Little White House. Known for its live music and festivals, cultural venues include Mel Fisher Maritime Museum, Florida Keys Eco - Discovery Center and Key West Shipwreck Museum. Other popular sights include Duval Street and Florida Keys Beaches.
What is a historic hotel like in Key West?
When you book a historic hotel, you'll sleep someplace that has an officially recognised national historic designation. A stately home, palace or even a lodge, old police station or skyscraper can be considered a historic hotel provided that it's a place of special interest. Traditional architecture and period features are often found in the public spaces and guestrooms of such 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, wheareas the term "historic hotel" is more commonly used in the U.S. though overall the terms are quite similar. The architecture and building of a historic hotel is generally what's most important. For a heritage hotel, often it's 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 expect to find, though efforts have been made to preserve treasured traditions and historic facades. Smart TVs, WiFi, updated bathroom facilities and the popular amenities found in most hotels will be available in a historic hotel. Rest assured that when you select a historic hotel in Key West, you won't find yourself staying at a place that's uncomfortable for guests or simply rundown.

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