A sunny street lined with historic buildings, a 'ONE WAY' sign, and a flagpole with flags.

Find Historic Hotels in Key West, FL

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Key West Historic Hotels

Tonight
Sep 22 - Sep 23
Tomorrow
Sep 23 - Sep 24
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Our top choices for Key West historic hotels

A balcony with a view of a street, a bench, and a potted plant.
A hotel lobby with a bar area, seating, and a fireplace.
A bar area with a Pegasus International Hotel sign, round tables, and metal chairs.
A multi-story building with a ground-level commercial space featuring a brightly lit storefront.

1. Pegasus International Hotel

Pegasus International Hotel
Old Town Key West
Canada
Shahid
￥17,202
￥27,294 total
includes taxes & fees
Oct 1 - Oct 2
Pegasus International Hotel
A wooden boardwalk leading to a beach with palm trees and a clear sky.
A large white building with a balcony, palm trees, and a brick pathway leading to the entrance.
An outdoor patio with wicker furniture and a ceiling fan, surrounded by lush greenery and a view of a residential area.
A grand hallway with ornate ironwork, a chandelier, and a wooden floor.

2. Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn
Key West Historic District
United States
Melissa
￥22,485
￥25,296 total
includes taxes & fees
Sep 23 - Sep 24
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 beach with palm trees and a clear sky.
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
Jeffrey M.
￥17,100
￥43,340 total
includes taxes & fees
Sep 23 - Sep 24
CORTEZ ~ Adults Only, 2nd Floor King Room w/Pool View at Azul Mansion!
A person swimming with a large, spiky, orange object.
A yellow building with a balcony, parked cars, and palm trees.
A covered wooden deck with white railings, leading to a building with green-framed windows.
A beach with clear water and gentle waves.

4. 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.
￥50,986
￥95,796 total
includes taxes & fees
Sep 26 - Sep 27
Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!
A pool area with lounge chairs, string lights, and a decorative wall.
A spacious kitchen with white cabinets, a marble countertop, and a dining area with a wooden table and bench.
A modern kitchen with white cabinets, a built-in oven, and a microwave.
A modern kitchen with white cabinets, a wooden floor, and a dining area with a table and chairs.

5. Perfect Location, Private Heated Pool, Pristine Luxury Home!

Perfect Location, Private Heated Pool, Pristine Luxury Home!
Old Town Key West
United States
Kim M.
Perfect Location, Private Heated Pool, Pristine Luxury Home!
A swimming pool with a wooden deck, a covered patio area, and a building with large windows and a covered porch.
A house with a porch, number 1318, and a small seating area with chairs.
A cozy living room with a white sofa, two wicker side tables, a fireplace, and a ceiling fan.
A living room with a beige sofa, a round wooden coffee table, and a wicker chair.

6. BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL

BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL
Key West Historic District
United States
Jennifer B.
￥86,521
￥217,856 total
includes taxes & fees
Sep 25 - Sep 26
BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL
A beach with a palm tree and clear blue water.
A narrow pathway flanked by white picket fences and a tree with pink flowers.
A covered porch with white railings and wicker furniture.
A clear blue swimming pool with lane dividers, a fenced deck area, and a view of the ocean in the background.

7. 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.
￥22,308
￥61,570 total
includes taxes & fees
Oct 6 - Oct 7
OLD TOWN STEPS TO DUVAL! LA DOLCE VITA SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST
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 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.

8. 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.
￥94,229
￥118,750 total
includes taxes & fees
Sep 28 - Sep 29
Two Bedroom Two Bath Poolside Villa Steps 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 living room with a television, a dining area with a table and chairs, and a cozy seating area with a patterned rug.
A two-story house with a balcony, a pool, and outdoor furniture.

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

Two Bedroom Two Bath Balcony Villa Steps from Duval!
Old Town Key West
United States
Michael W.
￥93,971
￥117,170 total
includes taxes & fees
Sep 27 - Sep 28
Two Bedroom Two Bath Balcony Villa Steps from Duval!
A bedroom with a large bed, a wooden headboard, a desk with a chair, a mirror, and a view of the kitchen and bathroom.
A neatly made bed with a patterned bedspread, a decorative pillow, and two bedside lamps on either side.
A hotel room with a bed, orange armchair, desk, and a large mirror.
A bathroom with a bathtub, toilet, sink, and shower curtain.

10. Studio Blu - Historic Key West Studio + Bikes

Studio Blu - Historic Key West Studio + Bikes
Old Town Key West
United States
Emily F.
￥25,438
￥55,444 total
includes taxes & fees
Sep 23 - Sep 24
Studio Blu - Historic Key West Studio + Bikes
View all properties

Top Key West Hotel Reviews

Hampton Inn Key West FL

Hampton Inn Key West FL

10/10 Excellent
"Me encantó la verdad muy limpio trankilo y para ir en familia y con niños lo recomiendo mucho gracias"
Suany 2-night trip
Posted 8 hours ago
Hampton Inn Key West FL
Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"Comfortable beds"
Paul 3-night trip
Posted 8 hours ago
Beachside Resort & Residences
Fairfield by Marriott Inn & Suites Key West at The Keys Collection

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

10/10 Excellent
"Nice place"
Travis 2-night trip
Posted 8 hours ago
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"A little annoyed at the gate that got locked (leading us to our room), and that the gate was not repaired during our stay, but that was the only real issue out of the entire stay."
Nicholas James 6-night trip
Posted 10 hours ago
Southernmost Beach Resort and Guesthouses
Ibis Bay Beach Resort

Ibis Bay Beach Resort

8/10 Good
"Great"
Sergio 2-night trip
Posted 11 hours ago
Ibis Bay Beach Resort
Southwinds Motel

Southwinds Motel

8/10 Good
"The room was clean and the staff very helpful"
Tony 2-night trip
Posted 14 hours ago
Southwinds Motel
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

10/10 Excellent
"Was a great place beds could use a little upgrade"
Joseph 4-night trip
Posted 1 day ago
Blue Flamingo Resort Key West
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

8/10 Good
"The hotel was clean, great customer service, and the food was really good!"
Craige 3-night trip
Posted 2 days ago
DoubleTree Resort by Hilton Grand Key - Key West

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 entertainment choices.
What's the best hotel in Key West to learn about local history?
Based on our travel expertise, Amsterdam's Curry Mansion Inn is a top historic guesthouse bookable on Expedia and it features free WiFi. Harry S. Truman Little White House is a short walk away. Other choices to soak up the local history include FLOR DE CANA ~ Adults-Only 2nd Floor Queen Room w/Pool View at Azul Mansion! and COHIBA~Adults Only, Poolview (2nd Floor) Queen Room in Historic Azul Mansion!.
How many historical hotels will I find in Key West?
In Key West, you'll find 2635 hotels and other accommodations bookable on Expedia, including 11 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, 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?
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.

Explore a world of travel with Expedia