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Historic Hotels & Resorts in Old Town Key West from AU$339

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Check availability on Old Town Key West Historic Hotels

Our top choices for Old Town Key West historic hotels

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$339
includes taxes & fees
28 Oct - 29 Oct
Pegasus International Hotel

2. HAVANA VIEJA ~ Adults Only, First Floor Queen Room w/ Community Pool!

HAVANA VIEJA ~ Adults Only, First Floor Queen Room w/ Community Pool!
Old Town Key West
9.6 out of 10, Exceptional, (172 reviews)
"One of our best vacations ever. Our room was steps from the pool and common areas. I would highly recommend staying here."
United States
Vicki L.
The price is AU$394
includes taxes & fees
25 Oct - 26 Oct
HAVANA VIEJA ~ Adults Only, First Floor Queen Room w/ Community Pool!

3. 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
9.6 out of 10, Exceptional, (157 reviews)
"Excellent location for a week in the Keys. Was able to walk to all the Duval Street attractions. "
United States
Michael R.
The price is AU$690
includes taxes & fees
9 Nov - 10 Nov
OLD TOWN STEPS TO DUVAL! LA DOLCE VITA SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST

4. Studio Blu - Historic Key West Studio + Bikes

Studio Blu - Historic Key West Studio + Bikes
Old Town Key West
10.0 out of 10, Exceptional, (123 reviews)
"Very communicative, property was as pictured and bikes were perfect for getting around. We didn’t need a car but had no trouble parking right next to the front door. Sandy’s had the best coffee and food was delicious! Will definitely come again!"
United States
Emily F.
The price is AU$540
includes taxes & fees
26 Oct - 27 Oct
Studio Blu - Historic Key West Studio + Bikes

5. 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!

6. 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$613
includes taxes & fees
25 Oct - 26 Oct
Poolside Studio Villa Steps from Duval!

7. 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$1,091
includes taxes & fees
29 Oct - 30 Oct
Two Bedroom Two Bath Poolside Villa Steps from Duval!

8. 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$1,055
includes taxes & fees
3 Nov - 4 Nov
Two Bedroom Two Bath Balcony Villa Steps from Duval!

9. 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$1,662
includes taxes & fees
17 Nov - 18 Nov
KAMP - Rooftop Penthouse Overlooking Duval

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

Poolside Paradise - Heated Pool & Steps to Duval St
Old Town Key West
9.0 out of 10, Wonderful, (26 reviews)
"Great location"
United States
Peter S.
The price is AU$1,712
includes taxes & fees
17 Nov - 18 Nov
Poolside Paradise - Heated Pool & Steps to Duval St
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.

Top Old Town Key West Hotel Reviews

Frequently asked questions

What should a history buff expect from a stay in Old Town Key West?
The historical places in Old Town Key West are likely at the top of your travel itinerary. And while you're visiting the area, why not also enjoy all there is to see and do?
What's the best accommodation in Old Town Key West to absorb the local history?
Based on our travel expertise, ARIA~Adult Only, Treetop King Suite w/ Balcony & Community Pool! is a top guest house on Expedia for those interested in history, and it features concierge services and free WiFi. Key West Cemetery is a short walk away. A couple of other options near historic sites 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 are located in Old Town Key West?
In Old Town Key West, there are 1278 hotels and other lodging options bookable on Expedia, including 12 historic hotels or hotels close to historic sites.
What are the top historical sites and other places to visit in Old Town Key West?
Old Town 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. Cultural venues include Florida Keys Eco - Discovery Center, Mel Fisher Maritime Museum and Museum of Art & History at the Custom House. Other popular sights include Duval Street and Florida Keys Beaches.
What is a historic hotel like in Old Town Key West?
Guests who book a historic hotel can sleep someplace that has an officially recognised national historic designation. A castle, stately home, palace or even a pub, lodge, old police station or skyscraper can be considered a historic hotel as long as it has special significance. Traditional architecture and period features are typically preserved in the communal spaces and guestrooms of these historic hotels in Old Town Key West, giving a historical feel.
What is the difference between a historic hotel and a heritage hotel?
You'll often hear the term "heritage hotel" in Asia and Europe, wheareas the term "historic hotel" is more commonly used in the U.S. but overall the terms are quite similar. The architecture and actual building of historic hotels are generally what's most significant. For a heritage hotel, mainly, it's cultural value and how it shaped the community.
Do historic hotels in Old Town Key West have modern facilities?
Hotels have the safety features and modern conveniences you've come to expect, while every effort is made to preserve the historic aspects and traditions. WiFi, heating and air conditioning, updated bathroom facilities, and the usual amenities found in a hotel will also be available in a historic hotel. Rest assured that when you choose a historic hotel in Old Town Key West, you won't find a place that is rundown or uncomfortable.

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