A coastal town with a prominent building featuring a blue awning, a chicken shack, and a store with colorful merchandise.

Historic Hotels & Resorts in Downtown Key West from AU$304

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Check availability on Downtown Key West Historic Hotels

Our top choices for Downtown Key West historic hotels

A balcony with a view of a street, a bench, and a potted plant.

1. Pegasus International Hotel

Pegasus International Hotel
2.5 star property
Old Town Key West
8.2 out of 10, Very good, (1,001 reviews)
"The hotel was located on duval street walking distance to everything Key West, the room was great and amenities were also great. Check in and out was easy and fast."
United States
Karla
The price is AU$304
includes taxes & fees
15 Oct - 16 Oct
Pegasus International Hotel
A two-story house with a swimming pool, outdoor seating, and a balcony with a yellow umbrella.

2. Poolside Studio Villa Steps from Duval!

Poolside Studio Villa Steps from Duval!
Old Town Key West
10.0 out of 10, Exceptional, (26 reviews)
"Great place to stay"
United States
Benjamin K.
The price is AU$594
includes taxes & fees
15 Oct - 16 Oct
Poolside Studio Villa Steps from Duval!
A mobile home with two air conditioning units, a white fence, and a white car parked in front.

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

Poolside Paradise - Heated Pool & Steps to Duval St
Old Town Key West
8.8 out of 10, Excellent, (24 reviews)
"Great location"
United States
Peter S.
The price is AU$2,187
includes taxes & fees
26 Oct - 27 Oct
Poolside Paradise - Heated Pool & Steps to Duval St
A two-story house with a swimming pool, outdoor seating, and a balcony with a yellow umbrella.

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

Two Bedroom Two Bath Poolside Villa Steps from Duval!
Old Town Key West
10.0 out of 10, Exceptional, (66 reviews)
"Cannot say enough good things about the Villas. They reached out to me weeks/days before and followed up during our stay. The happy hour and breakfast was an added bonus. Pool and rooms were awesome and location can’t be beat. Will stay there again!"
United States
Matt S.
The price is AU$1,114
includes taxes & fees
29 Oct - 30 Oct
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.

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

Two Bedroom Two Bath Balcony Villa Steps from Duval!
Old Town Key West
10.0 out of 10, Exceptional, (47 reviews)
"Great place to stay and great owners!"
United States
Michael W.
The price is AU$1,075
includes taxes & fees
15 Oct - 16 Oct
Two Bedroom Two Bath Balcony Villa Steps from Duval!
A spacious living room with large windows, a blue sofa, a green sectional, and a wooden ceiling.

6. KAMP - Rooftop Penthouse Overlooking Duval

KAMP - Rooftop Penthouse Overlooking Duval
Old Town Key West
8.4 out of 10, Very good, (23 reviews)
"We had a blast in Key West. The roof top Penthouse was PERFECT "
United States
Ward R.
The price is AU$1,725
includes taxes & fees
2 Nov - 3 Nov
KAMP - Rooftop Penthouse Overlooking Duval
A pool area with lounge chairs, string lights, and a decorative wall.

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

Perfect Location, Private Heated Pool, Pristine Luxury Home!
Old Town Key West
10.0 out of 10, Exceptional, (217 reviews)
"Great location! Home was just as advertised. Highly recommend."
United States
Stephanie B.
The price is AU$4,140
includes taxes & fees
10 Nov - 11 Nov
Perfect Location, Private Heated Pool, Pristine Luxury Home!
A wooden boardwalk leading to a beach with palm trees and a clear sky.

8. Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn
3.0 star property
Key West Historic District
8.2 out of 10, Very good, (1,013 reviews)
"If you like an old historical place to stay, this is it. Great location, big rooms, great atmosphere, free parking (bonus)"
United States
chris
The price is AU$428
includes taxes & fees
15 Oct - 16 Oct
Amsterdam's Curry Mansion Inn
A covered outdoor area with wicker furniture and a pool.

9. 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
9.6 out of 10, Exceptional, (172 reviews)
"Cute, clean, and great amenities"
United States
Cindy D.
The price is AU$408
includes taxes & fees
19 Oct - 20 Oct
FLOR DE CANA ~ Adults-Only 2nd Floor Queen Room w/Pool View at Azul Mansion!
A person swimming with a large, spiky, orange object.

10. 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
9.2 out of 10, Wonderful, (320 reviews)
"Great stay! Pool was a great amenity. Would definitely book again."
United States
Kayleigh V.
The price is AU$860
includes taxes & fees
27 Oct - 28 Oct
Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Downtown Key West Hotel Reviews

Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"Enjoyed our stay. The resort was very nice and we had the best time on the sandbar tour with Captain John!"
Mollie 3-night trip
Posted 2 hours ago
Beachside Resort & Residences

Frequently asked questions

What should a history buff expect from a stay in Downtown Key West?
You're likely already making plans to see the sights of historical relevance while on holiday in Downtown Key West. And don't forget to explore the many sights while you're visiting the area.
How many historical hotels are located in Downtown Key West?
Downtown Key West is home to 194 lodging options bookable on Expedia though you won't find many designated historic hotels.
What are the must-see historical sites and other places in Downtown Key West?
Downtown Key West is notable for landmarks like Ernest Hemingway Home and Museum. Duval Street is another popular sight to explore.
What is a historic hotel like in Downtown Key West?
By choosing a historic hotel, you can stay in a place that has an officially recognised historic designation. A palace, castle, stately home or even a lodge, pub or skyscraper can be identified as a historic hotel provided that it has special significance. Traditional architecture and period features are typically preserved in the public spaces and guestrooms of these historic hotels in Downtown Key West, giving a real sense of character.
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. but overall the terms are quite similar. The architecture and building of historic hotels are generally what's most significant. For a heritage hotel, mainly, it's cultural value and how it inspired the community.
Do historic hotels in Downtown Key West have modern facilities?
Hotels have the safety features and modern conveniences you expect to find, but every effort is made to preserve historic facades and treasured traditions. Private rooms with updated bathroom facilities, heating and air conditioning, free and fast Internet, and the amenities found in most hotels should be available at a historic hotel. When you choose a historic hotel in Downtown Key West, don't worry that you'll find yourself staying at a place that's uncomfortable or rundown.

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