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

Search Historic Hotels in Florida Keys

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Check availability on Florida Keys Historic Hotels

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

Our top choices for Florida Keys historic hotels

A balcony with a view of a street, a bench, and a potted plant.
A multi-story building with a ground-level commercial space featuring a brightly lit storefront.
A bar area with a Pegasus International Hotel sign, round tables, and metal chairs.
A reception desk with clocks, a Pegasus International Hotel sign, and a computer monitor.

1. Pegasus International Hotel

Pegasus International Hotel
Old Town Key West
United States
Vincent
£111
includes taxes & fees
27 Aug - 28 Aug
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 beach with palm trees and a clear sky.
A covered outdoor deck with wicker furniture and a white railing.

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.
£196
includes taxes & fees
2 Sept - 3 Sept
CORTEZ ~ Adults Only, King Room w/Pool View at Azul Mansion!
A kitchen with a refrigerator, stove, and two bar stools.
A kitchen with wooden cabinets, a stove, a refrigerator, and a dining table with a floral centerpiece.
A bedroom with a ceiling fan, wooden wardrobe, bedside table, and a TV.
A kitchen with a microwave, a white chair, and a table with a vase.

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
£212
includes taxes & fees
31 Aug - 1 Sept
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 grand hallway with ornate ironwork, a chandelier, and a wooden floor.
A large white building with a balcony, palm trees, and a brick pathway leading to the entrance.
A grand room with a large wooden door, a fireplace with a mantelpiece, and a chandelier.

4. Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn
Key West Historic District
United States
Melissa
£143
includes taxes & fees
31 Aug - 1 Sept
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.
Two orange armchairs with decorative pillows, a round coffee table with books, and a lamp.
A bedroom with a large bed, a wooden headboard, a desk with a chair, a mirror, and a view of the kitchen and bathroom.

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.
£250
includes taxes & fees
31 Aug - 1 Sept
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 coffee shop interior with a wooden counter, a coffee machine, and a display case with pastries.
An outdoor bar area with wooden chairs, a bar counter, hanging lights, and a water feature.
A yacht docked at a marina with a wooden deck, a pool, and string lights.

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.
£319
includes taxes & fees
27 Aug - 28 Aug
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 spacious room with a ceiling fan, large windows, a sofa, two wicker chairs, and a small table with decorative items.
A view through a window with a pool and outdoor furniture.
A wooden staircase with a view of greenery outside.

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
£184
includes taxes & fees
27 Aug - 28 Aug
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.
An open door to a room with a bed, a heart-shaped pillow, and a painting on the wall.
A kitchen with white cabinets, a microwave, a toaster, a coffee maker, a stove, and a refrigerator.

8. Poolside Studio Villa Steps from Duval!

Poolside Studio Villa Steps from Duval!
Old Town Key West
United States
Benjamin K.
£300
includes taxes & fees
3 Sept - 4 Sept
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.
£449
includes taxes & fees
27 Aug - 28 Aug
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 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.
A beach with palm trees and a clear sky.

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.
£184
includes taxes & fees
27 Aug - 28 Aug
CLARO ~ Adults Only, Pool View King Room in Azul Mansion!
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Top Florida Keys Hotel Reviews

Islander Resort

Islander Resort

10/10 Excellent
"Property is beautiful, staff is great and overall an amazing place to stay."
Sonia 1-night trip
Posted 18 hours ago
Islander Resort

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