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

Historic Hotels & Resorts in Key West from NZ$292

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Check availability on Key West Historic Hotels

Tonight
28 Sept - 29 Sept
Tomorrow
29 Sept - 30 Sept
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Key West historic hotels

A balcony with a view of a street, a bench, and a potted plant.
A reception desk with clocks, a Pegasus International Hotel sign, and a computer monitor.
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
United States
Karla
NZ$292
includes taxes & fees
1 Oct - 2 Oct
Pegasus International Hotel
A wooden boardwalk leading to a beach with palm trees and a clear sky.
A grand hallway with ornate ironwork, a chandelier, and a wooden floor.
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.

2. Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn
Key West Historic District
United States
Tiffany N
NZ$423
includes taxes & fees
30 Sept - 1 Oct
Amsterdam's Curry Mansion Inn
A covered outdoor deck with wicker furniture and a white railing.
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.
A beach with palm trees and a clear sky.

3. CLARO ~ Adults Only, Pool View (2nd Floor) King Room in Azul Mansion!

CLARO ~ Adults Only, Pool View (2nd Floor) King Room in Azul Mansion!
Old Town Key West
United States
Darcie B.
NZ$484
includes taxes & fees
30 Sept - 1 Oct
CLARO ~ Adults Only, Pool View (2nd Floor) King Room in Azul Mansion!
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 clear blue swimming pool with lane dividers, a fenced deck area, and a view of the ocean in the background.
A compact kitchen with a microwave, refrigerator, and a sink.

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.
NZ$714
includes taxes & fees
6 Oct - 7 Oct
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.
Two orange armchairs with decorative pillows, a round coffee table with books, and a lamp.
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.

5. Studio Blu - Historic Key West Studio + Bikes

Studio Blu - Historic Key West Studio + Bikes
Old Town Key West
United States
Emily F.
NZ$619
includes taxes & fees
29 Sept - 30 Sept
Studio Blu - Historic Key West Studio + Bikes
A beach with clear turquoise water, a sandy shore, and a distant ship.
A narrow pathway flanked by white picket fences and a tree with pink flowers.
A living room with a red sofa, a white armchair, a round coffee table, and a potted plant.
A clear blue swimming pool with lane dividers, a fenced deck area, and a view of the ocean in the background.

6. STEPS TO DUVAL, OLD TOWN! 'LA DOLCE VITA' SLEEPS 2-4, 3 BLKS TO STH BCH

STEPS TO DUVAL, OLD TOWN! 'LA DOLCE VITA' SLEEPS 2-4, 3 BLKS TO STH BCH
Old Town Key West
United States
Joseph
NZ$878
includes taxes & fees
6 Oct - 7 Oct
STEPS TO DUVAL, OLD TOWN! 'LA DOLCE VITA' SLEEPS 2-4, 3 BLKS TO STH BCH
A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.
A living room with a sofa, armchair, coffee table, and a cabinet with decorative items.
A bar with a signboard listing various destinations.
A pathway through a lush garden with various plants and trees.

7. 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
NZ$920
includes taxes & fees
29 Sept - 30 Sept
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 yellow building with a balcony, parked cars, and palm trees.
A beach with clear water and gentle waves.

8. 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.
NZ$1,172
includes taxes & fees
10 Oct - 11 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.
An open door to a room with a bed, a heart-shaped pillow, and a painting on the wall.
A kitchen with white cabinets, a microwave, a toaster, a coffee maker, a stove, and a refrigerator.

9. Poolside Studio Villa Steps from Duval!

Poolside Studio Villa Steps from Duval!
Old Town Key West
United States
Benjamin K.
Poolside Studio Villa Steps from Duval!
A spacious living room with large windows, a blue sofa, a green sectional, and a wooden ceiling.
A modern living room with a sectional sofa, a round wooden coffee table, and a black rug.
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.
NZ$2,200
includes taxes & fees
11 Oct - 12 Oct
KAMP - Rooftop Penthouse Overlooking Duval
View all properties

Top Key West Hotel Reviews

Hampton Inn Key West FL

Hampton Inn Key West FL

10/10 Excellent
"breakfast was amazing and the hot items changed daily. Pool temp was ideal :-) rooms were super clean and spacious (highly recommend the balcony room facing the ocean). shuttle into Key West is a huge bonus (you do not want to try and drive/park in downtown Key West)."
Amy 3-night trip
Posted 2 hours ago
Hampton Inn Key West FL
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent
"Close to everything, comfortable stay"
Nancy 2-night trip
Posted 2 hours ago
DoubleTree Resort by Hilton Grand Key - Key West
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
"Great stay! The breakfast was excellent, and the staff was very friendly and attentive. The room was clean and comfortable. Everything was very nice overall."
Fan 2-night trip
Posted 15 hours ago
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

8/10 Good
"Staff of the bus drivers was fantastic. Food was delish, the joint properties amenities usage was amazing and the staff was super helpful."
Joanna 6-night trip
Posted 15 hours ago
Hilton Garden Inn Key West / The Keys Collection
Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"Great location and superb private beach"
Stian 3-night trip
Posted 16 hours ago
Pier House Resort & Spa
Southwinds Motel

Southwinds Motel

10/10 Excellent
"Wonderful"
Hossein 2-night trip
Posted 17 hours ago
Southwinds Motel
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

10/10 Excellent
"Excellent getaway spot for families or big groups. We loved it. Had a great time celebrating my bday! ✨"
Angelica 2-night trip
Posted 21 hours ago
Parrot Key Hotel & Villas
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

10/10 Excellent
"Great location"
Mary 5-night trip
Posted 2 days ago
La Concha Key West, Autograph Collection
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent
"From before we arrived we already knew we chose the right place to stay! We had questions about parking our motorcycle on property and there was no hesitation to share information and also connect with us. The staff is great. We are recommending this location and properties to friends and family. Next time we’re in town, 100% this will be the place we stay. Location is great and the property is fun to explore. Thank you all for making our stay memorable!"
Rebecca 2-night trip
Posted 4 days ago
Winslow's Bungalows - Key West Historic Inns

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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