A beach with palm trees, people relaxing on chairs, and colorful kayaks.

Find Historic Hotels in Florida Keys

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Florida Keys Historic Hotels

Tonight
Aug 26 - Aug 27
Tomorrow
Aug 27 - Aug 28
This weekend
Aug 28 - Aug 30
Next weekend
Sep 4 - Sep 6

Our top choices for Florida Keys 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
Vincent
￥13,117
￥22,811 total
includes taxes & fees
Aug 27 - Aug 28
Pegasus International Hotel
A living room with two sofas, a coffee table, and a window with blinds.
A pool area with lounge chairs, a pool with clear blue water, and a covered patio with outdoor seating.
A covered outdoor deck with wicker furniture and a white railing.
A beach with palm trees and a clear sky.

2. CORTEZ ~ Adults Only, King Room w/Pool View at Azul Mansion!

CORTEZ ~ Adults Only, King Room w/Pool View at Azul Mansion!
Old Town Key West
United States
Jeffrey M.
￥15,602
￥41,692 total
includes taxes & fees
Aug 30 - Aug 31
CORTEZ ~ Adults Only, King Room w/Pool View at Azul Mansion!
A kitchen with a refrigerator, stove, and two bar stools.
A kitchen with a microwave, a white chair, and a table with a vase.
A bedroom with a ceiling fan, wooden wardrobe, bedside table, and a TV.
A compact kitchen with wooden cabinets, a white refrigerator, and a small sink.

3. Aug.-Sept. Special@119.lodging Only 119. + extras. From.8-17 to 9-30

Aug.-Sept. Special@119.lodging Only 119. + extras. From.8-17 to 9-30
Old Town Key West
United States
Jeanine
￥17,050
￥45,770 total
includes taxes & fees
Aug 31 - Sep 1
Aug.-Sept. Special@119.lodging Only 119. + extras. From.8-17 to 9-30
A wooden boardwalk leading to a beach with palm trees and a clear sky.
A large white building with a balcony, palm trees, and a brick pathway leading to the entrance.
A grand hallway with ornate ironwork, a chandelier, and a wooden floor.
An outdoor patio with wicker furniture and a ceiling fan, surrounded by lush greenery and a view of a residential area.

4. Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn
Key West Historic District
United States
Melissa
￥27,828
￥31,306 total
includes taxes & fees
Aug 31 - Sep 1
Amsterdam's Curry Mansion Inn
A pathway leading to a house with a number '121' on the wall, surrounded by potted plants.
A compact kitchen with a dining area, featuring a small island, cabinets, and a window with a view.
A compact kitchen with a microwave, toaster, sink, and a small refrigerator.
Two orange armchairs with decorative pillows, a round coffee table with books, and a lamp.

5. 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
United States
Emily F.
￥23,187
￥53,467 total
includes taxes & fees
Aug 31 - Sep 1
Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
A compact kitchen with a dishwasher, a microwave, and a sink. There is a window with a view of the outdoors, and a ceiling fan.
A yacht docked at a marina with a wooden deck, a pool, and string lights.
A balcony with a view of a marina, a wooden chair, a potted plant, and a welcome mat.
An outdoor bar area with wooden chairs, a bar counter, hanging lights, and a water feature.

6. Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures

Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
Tavernier
United States
Jamie B.
￥39,402
￥70,198 total
includes taxes & fees
Aug 27 - Aug 28
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
A covered outdoor area with a table and chairs, surrounded by white railings and palm trees.
A wooden staircase with a view of greenery outside.
A view through a window with a pool and outdoor furniture.
A spacious room with a ceiling fan, large windows, a sofa, two wicker chairs, and a small table with decorative items.

7. CORONA ~ Adults Only, King Room with Community Pool at Azul Mansion!

CORONA ~ Adults Only, King Room with Community Pool at Azul Mansion!
Old Town Key West
United States
Anthony
￥14,159
￥39,893 total
includes taxes & fees
Aug 27 - Aug 28
CORONA ~ Adults Only, King Room with Community Pool at Azul Mansion!
A two-story house with a swimming pool, outdoor seating, and a balcony with a yellow umbrella.
A room with a bed, a dining table, and a kitchen area.
A kitchen with white cabinets, a microwave, a toaster, a coffee maker, a stove, and a refrigerator.
A property named Villas Key West with a covered entrance, a white picket fence, and lush greenery.

8. Poolside Studio Villa Steps from Duval!

Poolside Studio Villa Steps from Duval!
Old Town Key West
United States
Benjamin K.
￥52,377
￥66,407 total
includes taxes & fees
Sep 3 - Sep 4
Poolside Studio Villa Steps from Duval!
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 beach with clear water and gentle waves.
A yellow building with a balcony, parked cars, and palm trees.

9. 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.
￥51,704
￥97,145 total
includes taxes & fees
Aug 27 - Aug 28
Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!
A covered outdoor deck with wicker furniture and a white railing.
A beach with palm trees and a clear sky.
A living room with a large painting, a glass coffee table, a beige sofa, and a view through a glass door to an outdoor area with plants.
A pool area with lounge chairs, a pool with clear blue water, and a covered patio with outdoor seating.

10. CLARO ~ Adults Only, Pool View King Room in Azul Mansion!

CLARO ~ Adults Only, Pool View King Room in Azul Mansion!
Old Town Key West
United States
Ashley S.
￥14,159
￥39,893 total
includes taxes & fees
Aug 27 - Aug 28
CLARO ~ Adults Only, Pool View King Room in Azul Mansion!
View all properties

Top Florida Keys Hotel Reviews

Islander Resort

Islander Resort

10/10 Excellent
"Spectacular remodel. Every room has a generous patio."
Marcela 1-night trip
Posted 1 hour ago
Islander Resort

Explore a world of travel with Expedia