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

Find Historic Hotels in Florida Keys from CA $198

  • 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

Sundeck
Reception
Breakfast area
Street view

1. Pegasus International Hotel

Pegasus International Hotel
Old Town Key West
United States
Vincent
CA $114
CA $198 total
includes taxes & fees
Aug 30 - Aug 31
Pegasus International Hotel
Living area
Pool
Beach
Terrace/patio

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.
CA $136
CA $360 total
includes taxes & fees
Aug 30 - Aug 31
CORTEZ ~ Adults Only, King Room w/Pool View at Azul Mansion!
Interior
Private kitchen
Dining
Room

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
CA $148
CA $396 total
includes taxes & fees
Aug 31 - Sep 1
Aug.-Sept. Special@119.lodging Only 119. + extras. From.8-17 to 9-30
Beach
Hallway
Outdoor dining
Exterior

4. Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn
Key West Historic District
United States
Melissa
CA $237
CA $266 total
includes taxes & fees
Aug 31 - Sep 1
Amsterdam's Curry Mansion Inn
Exterior detail
Private kitchen
Private kitchen
Room

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.
CA $202
CA $465 total
includes taxes & fees
Aug 31 - Sep 1
Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
Private kitchen
Property grounds
Dining
Bar (on property)

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.
CA $380
CA $653 total
includes taxes & fees
Sep 6 - Sep 7
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
Outdoor dining
Beach
Pool
Living area

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
CA $123
CA $344 total
includes taxes & fees
Aug 27 - Aug 28
CORONA ~ Adults Only, King Room with Community Pool at Azul Mansion!
Pool
Terrace/patio
Exterior
Private kitchen

8. Poolside Studio Villa Steps from Duval!

Poolside Studio Villa Steps from Duval!
Old Town Key West
United States
Benjamin K.
CA $455
CA $572 total
includes taxes & fees
Sep 4 - Sep 5
Poolside Studio Villa Steps from Duval!
Beach
Beach
Property grounds
Exterior

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.
CA $450
CA $848 total
includes taxes & fees
Aug 28 - Aug 29
Raphael Suite: 2/2 Studio Rooms - Pool, Patio w/grill, 2 blocks from Duval!
Terrace/patio
Interior
Pool
Beach

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.
CA $123
CA $344 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
"Property is beautiful, staff is great and overall an amazing place to stay."
Sonia 1-night trip
Posted 15 hours ago
Islander Resort

Explore a world of travel with Expedia