A sunset over a coastal landscape with a small island surrounded by water.

Find Historic Hotels in Stock Island, FL

  • 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 Stock Island Historic Hotels

Tonight
Oct 1 - Oct 2
Tomorrow
Oct 2 - Oct 3
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Stock Island historic hotels

A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.
A bar with a signboard listing various destinations.
A two-story house with a front porch, a staircase, and a garage.
A pathway through a lush garden with various plants and trees.

1. Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS

Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
Stock Island
United States
Linda
￥47,465
￥98,896 total
includes taxes & fees
Oct 7 - Oct 8
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
A wooden boardwalk leading to a beach with palm trees and a clear sky.
A grand room with a large wooden door, a fireplace with a mantelpiece, and a chandelier.
A large white building with a balcony, palm trees, and a brick pathway leading to the entrance.
An outdoor patio with wicker furniture and a ceiling fan, surrounded by lush greenery and a view of a residential area.

2. Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn
Key West Historic District
United States
Tiffany N
￥20,092
￥22,603 total
includes taxes & fees
Oct 5 - Oct 6
Amsterdam's Curry Mansion Inn
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 reception desk with clocks, a Pegasus International Hotel sign, and a computer monitor.
A hotel lobby with a bar area, seating, and a fireplace.

3. Pegasus International Hotel

Pegasus International Hotel
Old Town Key West
United States
Karla
￥18,601
￥28,896 total
includes taxes & fees
Oct 6 - Oct 7
Pegasus International Hotel
A covered outdoor deck with wicker furniture and a white railing.
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 wooden staircase with a view of greenery outside.

4. CLARO ~ Adults Only, Pool View (2nd Floor) King Room in Azul Mansion!

CLARO ~ Adults Only, Pool View (2nd Floor) King Room in Azul Mansion!
Old Town Key West
United States
Darcie B.
￥15,428
￥41,385 total
includes taxes & fees
Oct 4 - Oct 5
CLARO ~ Adults Only, Pool View (2nd Floor) King Room in Azul Mansion!
A bedroom with a large bed, a wooden headboard, a desk with a chair, a mirror, and a view of the kitchen and bathroom.
A narrow pathway leading to a house with a blue exterior, a number '12' sign, and various potted plants.
Two orange armchairs with decorative pillows, a round coffee table with books, and a lamp.
A well-lit bedroom with a large bed, a desk, a chair, and a sofa. There are multiple pillows, a lamp, and a plant on the bedside table.

5. Studio Blu - Historic Key West Studio + Bikes

Studio Blu - Historic Key West Studio + Bikes
Old Town Key West
United States
Emily F.
￥25,527
￥55,796 total
includes taxes & fees
Oct 5 - Oct 6
Studio Blu - Historic Key West Studio + Bikes
A covered outdoor area with wicker furniture and a pool.
A wooden staircase with a view of greenery outside.
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.

6. COHIBA~Adults Only, Poolview (2nd Floor) Queen Room in Historic Azul Mansion!

COHIBA~Adults Only, Poolview (2nd Floor) Queen Room in Historic Azul Mansion!
Old Town Key West
United States
Patrick
￥17,160
￥43,334 total
includes taxes & fees
Oct 8 - Oct 9
COHIBA~Adults Only, Poolview (2nd Floor) Queen Room in Historic Azul Mansion!
A living room with two sofas, a coffee table, and a window with blinds.
A wooden staircase with a view of greenery outside.
A covered outdoor deck with wicker furniture and a white railing.
A beach with palm trees and a clear sky.

7. HAVANA VIEJA ~ Adults Only, First Floor Queen Room w/ Community Pool!

HAVANA VIEJA ~ Adults Only, First Floor Queen Room w/ Community Pool!
Old Town Key West
United States
Ron C.
￥17,160
￥43,492 total
includes taxes & fees
Oct 6 - Oct 7
HAVANA VIEJA ~ Adults Only, First Floor Queen Room w/ Community Pool!
A covered outdoor deck with wicker furniture and a white railing.
A beach with palm trees and a clear sky.
A wooden staircase with a view of greenery outside.
A spacious room with a ceiling fan, large windows, a sofa, two wicker chairs, and a small table with decorative items.

8. FUENTE ~ Adults Only, 2nd Floor, Pool View, King Room at Azul Mansion!

FUENTE ~ Adults Only, 2nd Floor, Pool View, King Room at Azul Mansion!
Old Town Key West
United States
Emily K.
￥18,104
￥44,554 total
includes taxes & fees
Oct 8 - Oct 9
FUENTE ~ Adults Only, 2nd Floor, Pool View, King Room at Azul Mansion!
A covered outdoor area with wicker furniture and a pool.
A beach with palm trees and a clear sky.
A pool area with lounge chairs, a pool with clear blue water, and a covered patio with outdoor seating.
A spacious room with a ceiling fan, large windows, a sofa, two wicker chairs, and a small table with decorative items.

9. FLOR DE CANA ~ Adults-Only 2nd Floor Queen Room w/Pool View at Azul Mansion!

FLOR DE CANA ~ Adults-Only 2nd Floor Queen Room w/Pool View at Azul Mansion!
Old Town Key West
United States
Jake H.
￥16,530
￥42,783 total
includes taxes & fees
Oct 3 - Oct 4
FLOR DE CANA ~ Adults-Only 2nd Floor Queen Room w/Pool View at Azul Mansion!
A living room with two sofas, a coffee table, and a window with blinds.
A beach with palm trees and a clear sky.
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.

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

CORTEZ ~ Adults Only, 2nd Floor King Room w/Pool View at Azul Mansion!
Old Town Key West
United States
Jeffrey M.
￥16,530
￥42,783 total
includes taxes & fees
Oct 4 - Oct 5
CORTEZ ~ Adults Only, 2nd Floor King Room w/Pool View at Azul Mansion!
View all properties

Top Stock Island Hotel Reviews

Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"Good"
sai krishna 3-night trip
Posted less than an hour ago
Beachside Resort & Residences
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

8/10 Good
"Bar service was good. No Hot tub at main pool. Did have one on property next door. Easy access but a little bit of a drive to Deval street."
Gary 2-night trip
Posted 1 hour ago
Blue Flamingo Resort Key West
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

8/10 Good
"Valet parking obligatoire ce qui était pour nous plutôt une nuisance qu’un avantage car nous sortions souvent visiter les alentours! Nous ne pouvions pas apporter de boissons alcoolisé au bord de la piscine il fallait les acheter directement au bar de piscine …"
Alexandre 1-night trip
Posted 4 hours ago
Parrot Key Hotel & Villas
Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"Pier house is the best place in Key West! Won’t stay anywhere else. Staff is incredible. Looking forward to this year."
James 5-night trip
Posted 8 hours ago
Pier House Resort & Spa
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent
"The property was immaculate, the staff friendly and the location was perfect. We love that the resort allows you access to The Reach, which is basically next door. You are able to use all of their amenities as well and charge them to Your room. We had a beach front room with a balcony. It was beautiful!"
Amber Dawn 4-night trip
Posted 9 hours ago
Casa Marina Key West, Curio Collection by Hilton
Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

10/10 Excellent
"We had a wonderful stay at Hyatt Centric Key West Resort & Spa! The pool was a perfect place to relax, and we especially loved seeing the rescued turtles - such a unique and memorable part of the property. The location could not be better: everything we wanted to explore in Key West was within easy walking distance. It was incredibly convenient to enjoy the sights, restaurants, and lively atmosphere without needing a car. We would gladly stay here again!"
Christy 2-night trip
Posted 3 days ago
Hyatt Centric Key West Resort and Spa
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

8/10 Good
"Thank you"
Agustin 2-night trip
Posted 3 days ago
Hilton Garden Inn Key West / The Keys Collection

Explore a world of travel with Expedia