A white building with shutters, palm trees, and a lawn.

Historic Hotels & Resorts in Old Town Key West from AU$264

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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, (1,004 reviews)
"Exceptional location, good price for Key West which came with parking. I am definitely going to return to this place and recommend to others !!."
Canada
Shahid
The price is AU$264
includes taxes & fees
26 Sept - 27 Sept
Pegasus International Hotel

2. 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$583
includes taxes & fees
6 Oct - 7 Oct
OLD TOWN STEPS TO DUVAL! LA DOLCE VITA SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST

3. Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!

Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
Old Town Key West
10.0 out of 10, Exceptional, (122 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$464
includes taxes & fees
12 Sept - 13 Sept
Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!

4. 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
9.8 out of 10, Exceptional, (52 reviews)
"The apartment is good size and comfortable but the location is fantastic.walking distance to all of old town bars and restaurants. Three blocks to southernmost point. We walked to everything definitely would love to come back here and totally recommend"
United States
Joseph
STEPS TO DUVAL, OLD TOWN! 'LA DOLCE VITA' SLEEPS 2-4, 3 BLKS TO STH BCH

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, (318 reviews)
"Great stay! Pool was a great amenity. Would definitely book again."
United States
Kayleigh V.
The price is AU$855
includes taxes & fees
8 Sept - 9 Sept
Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!

6. KAMP - Rooftop Penthouse Overlooking Duval

KAMP - Rooftop Penthouse Overlooking Duval
Old Town Key West
8.4 out of 10, Very good, (22 reviews)
"We had a blast in Key West. The roof top Penthouse was PERFECT "
United States
Ward R.
The price is AU$1,096
includes taxes & fees
16 Sept - 17 Sept
KAMP - Rooftop Penthouse Overlooking Duval

7. 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.
Poolside Paradise - Heated Pool & Steps to Duval St

8. 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, (63 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.
Two Bedroom Two Bath Poolside Villa Steps from Duval!

9. 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, (215 reviews)
"Perfect spot to enjoy Key West and relax with friends! "
United States
Kim M.
The price is AU$2,588
includes taxes & fees
10 Sept - 11 Sept
Perfect Location, Private Heated Pool, Pristine Luxury Home!
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. Saint Mary Star of the Sea is a short walk away. A couple of other options near historic sites include FLOR DE CANA ~ Adults Only, Queen Room w/Pool View at Azul Mansion! and COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!.
How many historical hotels are located in Old Town Key West?
In Old Town Key West, there are 1281 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 Tennessee Williams Key West Exhibit. 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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