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

Historic Hotels & Resorts in Key West from AU$304

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Check availability on Key West Historic Hotels

Tonight
14 Oct - 15 Oct
Tomorrow
15 Oct - 16 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 hotel lobby with a bar area, seating, and a fireplace.
A reception desk with clocks, a Pegasus International Hotel sign, and a computer monitor.
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
United States
Karla
AU$304
includes taxes & fees
15 Oct - 16 Oct
Pegasus International Hotel
A wooden boardwalk leading to a beach with palm trees and a clear sky.
A grand room with a large wooden door, a fireplace with a mantelpiece, and a chandelier.
A grand hallway with ornate ironwork, a chandelier, and a wooden floor.
An outdoor patio with wicker furniture and a ceiling fan, surrounded by lush greenery and a view of a residential area.

2. Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn
Key West Historic District
United States
chris
AU$421
includes taxes & fees
15 Oct - 16 Oct
Amsterdam's Curry Mansion Inn
A covered outdoor area with wicker furniture and a pool.
A spacious room with a ceiling fan, large windows, a sofa, two wicker chairs, and a small table with decorative items.
A wooden staircase with a view of greenery outside.
A pool area with lounge chairs, a pool with clear blue water, and a covered patio with outdoor seating.

3. FLOR DE CANA ~ Adults-Only 2nd Floor Queen Room w/Pool View at Azul Mansion!

FLOR DE CANA ~ Adults-Only 2nd Floor Queen Room w/Pool View at Azul Mansion!
Old Town Key West
United States
Cindy D.
AU$400
includes taxes & fees
19 Oct - 20 Oct
FLOR DE CANA ~ Adults-Only 2nd Floor Queen Room w/Pool View at Azul Mansion!
A beach with people sunbathing and swimming, a clear blue sky, and a calm sea.
A narrow pathway flanked by white picket fences and a tree with pink flowers.
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.

4. 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.
AU$693
includes taxes & fees
9 Nov - 10 Nov
OLD TOWN STEPS TO DUVAL! LA DOLCE VITA SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST
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 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 narrow pathway leading to a house with a blue exterior, a number '12' sign, and various potted plants.
A kitchen with a built-in oven, a toaster, and a coffee maker.

5. Studio Blu - Historic Key West Studio + Bikes

Studio Blu - Historic Key West Studio + Bikes
Old Town Key West
United States
Emily F.
AU$596
includes taxes & fees
26 Oct - 27 Oct
Studio Blu - Historic Key West Studio + Bikes
A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.
A pathway through a lush garden with various plants and trees.
A living room with a sofa, armchair, coffee table, and a cabinet with decorative items.
A two-story house with a front porch, a staircase, and a garage.

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
AU$728
includes taxes & fees
18 Oct - 19 Oct
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
A person swimming with a large, spiky, orange object.
A wooden-paneled room with a bed, a television mounted on the wall, and a door leading to another room.
A covered wooden deck with white railings, leading to a building with green-framed windows.
A beach with clear water and gentle waves.

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.
AU$857
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 kitchen with white cabinets, a microwave, a toaster, a coffee maker, a stove, and a refrigerator.
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.
AU$591
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 property named Villas Key West with a covered entrance, a white picket fence, and lush greenery.
A house with a porch, a table, and a chair.
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.

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.
AU$1,109
includes taxes & fees
29 Oct - 30 Oct
Two Bedroom Two Bath Poolside Villa Steps from Duval!
A mobile home with two air conditioning units, a white fence, and a white car parked in front.
A living room with a sofa, coffee table, and a red chair. There is a ceiling fan and a window with blinds.
A backyard with a swimming pool, a barbecue grill, and a covered patio area.
A compact kitchen with a coffee maker, microwave, and refrigerator.

10. Poolside Paradise - Heated Pool & Steps to Duval St

Poolside Paradise - Heated Pool & Steps to Duval St
Old Town Key West
United States
Peter S.
AU$1,896
includes taxes & fees
28 Oct - 29 Oct
Poolside Paradise - Heated Pool & Steps to Duval St
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Top Key West Hotel Reviews

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

10/10 Excellent
"This hotel campus was perfect for our stay. There are 2 pools and lots of activities for the kiddos. Definitely family friendly which can be tricky in the keys. Free shuttle got us to and from Duval street. Wpuld stay there again."
Michele 1-night trip
Posted 1 hour ago
Blue Flamingo Resort Key West
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

10/10 Excellent
"Samantha and Sharon were extremely helpful and made this day memorable. Thank you."
Jeff 1-night trip
Posted 2 hours ago
Hilton Garden Inn Key West / The Keys Collection
The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

10/10 Excellent
"great location just off upper Duval Street."
Janine 4-night trip
Posted 2 hours ago
The Southernmost Inn - Adults Only
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"Great location. Friendly staff"
Elizabeth 8-night trip
Posted 4 hours ago
Southernmost Beach Resort and Guesthouses
Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"We have stayed at the Pier House in the past and enjoyed it. Over the years, we have tried other Vrbo’s and Hotels, but for us the Pier House is our favorite. The location, people and amenities make it the winner for us! You can’t be anymore centrally located than #1 Duval St."
Wayne Allen 5-night trip
Posted 6 hours ago
Pier House Resort & Spa
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent
"The beach was not swimma"
Kamila 4-night trip
Posted 19 hours ago
Casa Marina Key West, Curio Collection by Hilton
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent
"Beautiful resort. Very good restaurant on site. Shuttle bus to and from Old Town Key West every hour. The staff was exceptional. Highly recommend this resort."
William 1-night trip
Posted 22 hours ago
DoubleTree Resort by Hilton Grand Key - Key West
Hilton Key West Resort & Marina

Hilton Key West Resort & Marina

10/10 Excellent
"We went to Duval Street and Town Everyday, The Hilton KW Resort & Marina Shuttle Driver “Fausto” was a 15 Star!! He was so accommodating, professional, helpful people person, on time and just a Genuine Nice Guy! Wish everyone that we meant was like him!! Top Notch!!!!!👏👏🙌🙌 🌟🌟💫"
Michelle 5-night trip
Posted 1 day ago
Hilton Key West Resort & Marina
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
"Clean room , could not check in “not even 1 minute before exact time (very strictly on that). Breakfast was nice. We liked it overall"
Rolando 1-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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