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 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.
A hotel lobby with a bar area, seating, and a fireplace.

1. Pegasus International Hotel

Pegasus International Hotel
Old Town Key West
United States
Vincent
NT$2,628
NT$4,571 total
includes taxes & fees
Aug 27 - Aug 28
Pegasus International Hotel
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 room with a large wooden door, a fireplace with a mantelpiece, and a chandelier.
A grand hallway with ornate ironwork, a chandelier, and a wooden floor.

2. Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn
Key West Historic District
United States
Melissa
NT$5,770
NT$6,491 total
includes taxes & fees
Aug 27 - Aug 28
Amsterdam's Curry Mansion Inn
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 2 hours ago
Islander Resort

Explore a world of travel with Expedia