Historic Hotels & Resorts in Key West from NZ$423

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Check availability on Key West Historic Hotels

Tonight
30 Dec - 31 Dec
Tomorrow
31 Dec - 1 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Key West historic hotels

Outdoor spa tub
NYAH Key West - Adults Only

NYAH Key West - Adults Only

NYAH Key West - Adults Only
3.0 star property
Key West Historic District
8.0 out of 10, Very good, (1004)
"Great stay"
United States
Venkata Durga Phanindra Reddy
NYAH Key West - Adults Only
Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas, pool loungers
Heron House Court - Adult Only

Heron House Court - Adult Only

Heron House Court - Adult Only
3.0 star property
Key West Historic District
9.0 out of 10, Wonderful, (1003)
"Great staff, very friendly. Oerfect location, short walk to Duval, but far enough to get sleep. "
United States
Chandler
The price is NZ$423
includes taxes & fees
14 Jan - 15 Jan 2026
Heron House Court - Adult Only
Exterior
Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West
3.5 star property
Old Town Key West
8.6 out of 10, Excellent, (325)
"Great location and staff was friendly. The pool area was perfect. "
United States
Deborah
The price is NZ$608
includes taxes & fees
6 Jan - 7 Jan 2026
Hyatt Vacation Club at Sunset Harbor, Key West
Beach nearby
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!

HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!

HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!
Old Town Key West
9.6 out of 10, Exceptional, (152)
"Had a wonderful visit and everything was amazing I would highly recommend this place "
United States
Joel
The price is NZ$514
includes taxes & fees
5 Jan - 6 Jan 2026
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!
Exterior
Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa
4.0 star property
Key West Historic District
9.0 out of 10, Wonderful, (1002)
"Staff was courteous and the location is perfect for a weekend in Key West."
United States
TIMOTHY
The price is NZ$847
includes taxes & fees
12 Jan - 13 Jan 2026
Hyatt Centric Key West Resort and Spa
King Room D | Balcony
Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages
2.5 star property
Key West Historic District
9.8 out of 10, Exceptional, (886)
"I loved staying here! The room was great and the staff was awesome! "
United States
Tiffany
The price is NZ$435
includes taxes & fees
5 Jan - 6 Jan 2026
Simonton Court Historic Inn & Cottages
Front of property – evening/night
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West
4.0 star property
Old Town Key West
9.2 out of 10, Wonderful, (1029)
"Our stay was great!"
United States
Richard
The price is NZ$879
includes taxes & fees
4 Jan - 5 Jan 2026
Opal Key Resort & Marina, Key West
Exterior
Heron House - Adult Only

Heron House - Adult Only

Heron House - Adult Only
3.5 star property
Old Town Key West
9.0 out of 10, Wonderful, (1141)
"Clean room and staff was great"
United States
Paul
The price is NZ$447
includes taxes & fees
5 Jan - 6 Jan 2026
Heron House - Adult Only
Exterior detail
Balcony, Pool, & Near Duval - Curry House Room 8

Balcony, Pool, & Near Duval - Curry House Room 8

Balcony, Pool, & Near Duval - Curry House Room 8
Old Town Key West
9.2 out of 10, Wonderful, (22)
"Place is perfect"
United States
Ryan S.
The price is NZ$668
includes taxes & fees
4 Jan - 5 Jan 2026
Balcony, Pool, & Near Duval - Curry House Room 8
Sun deck
Pegasus International Hotel

Pegasus International Hotel

Pegasus International Hotel
2.5 star property
Old Town Key West
8.2 out of 10, Very good, (1005)
"We'd definitely stay here again. Very spacious king room and comfy bed. "
United States
Jessica
Pegasus International Hotel
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.
View all properties

Top Key West Hotel Reviews

Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

10/10 Excellent
"The bed was so comfortable and the room was nice and clean! "
Yolanda 1-night trip
Posted 2 days ago
Hyatt Vacation Club at Beach House, Key West

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 lively festivals and scenic seaside. You can also discover the area's great live music.
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. Audubon House and Tropical Gardens is a short walk away. Other choices near historic sites include COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion! and FLOR DE CANA ~ Adults Only, Queen Room w/Pool View at Azul Mansion!.
How many historical hotels are there in Key West?
In Key West, you'll find 2776 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 Audubon House and Tropical Gardens, Florida Keys Eco - Discovery Center and Key West Shipwreck Museum. Duval Street is another popular sight to explore.
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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