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
10 Oct - 11 Oct
Tomorrow
11 Oct - 12 Oct
Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct

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 two-story house with a front porch, a staircase, and a garage.
A bar with a signboard listing various destinations.
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
AED 777
AED 1,910 total
includes taxes & fees
12 Oct - 13 Oct
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 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.
A grand room with a large wooden door, a fireplace with a mantelpiece, and a chandelier.

2. Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn
Key West Historic District
United States
chris
AED 694
AED 1,153 total
includes taxes & fees
15 Oct - 16 Oct
Amsterdam's Curry Mansion Inn
A covered outdoor area with a table and chairs, surrounded by white railings and palm trees.
A large window with multiple panes overlooking a swimming pool and lush greenery.
A spacious room with a ceiling fan, large windows, a sofa, two wicker chairs, and a small table with decorative items.
A wooden staircase with a view of greenery outside.

3. CORONA ~ Adults Only, 2nd Floor King Room w/ Community Pool at Azul Mansion!

CORONA ~ Adults Only, 2nd Floor King Room w/ Community Pool at Azul Mansion!
Old Town Key West
United States
The Rogue P.
CORONA ~ Adults Only, 2nd Floor King Room w/ Community Pool at Azul Mansion!
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.

4. Pegasus International Hotel

Pegasus International Hotel
Old Town Key West
United States
Karla
AED 418
AED 657 total
includes taxes & fees
12 Oct - 13 Oct
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 wooden staircase with a view of greenery outside.
A beach with palm trees and a clear sky.

5. 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
Vicki L.
AED 580
AED 1,239 total
includes taxes & fees
25 Oct - 26 Oct
HAVANA VIEJA ~ Adults Only, First Floor Queen Room w/ Community Pool!
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.

6. 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
Cindy D.
AED 349
AED 950 total
includes taxes & fees
12 Oct - 13 Oct
CORTEZ ~ Adults Only, 2nd Floor King Room w/Pool View at Azul Mansion!
A covered outdoor area with wicker furniture and a pool.
A spacious room with a ceiling fan, large windows, a sofa, two wicker chairs, and a small table with decorative items.
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.

7. 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
Cindy D.
AED 441
AED 1,067 total
includes taxes & fees
19 Oct - 20 Oct
FLOR DE CANA ~ Adults-Only 2nd Floor Queen Room w/Pool View at 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 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.
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.

8. Studio Blu - Historic Key West Studio + Bikes

Studio Blu - Historic Key West Studio + Bikes
Old Town Key West
United States
Emily F.
AED 684
AED 1,420 total
includes taxes & fees
26 Oct - 27 Oct
Studio Blu - Historic Key West Studio + Bikes
A covered outdoor deck with wicker furniture and a white railing.
A wooden staircase with a view of greenery outside.
A beach with palm trees and a clear sky.
A spacious room with a ceiling fan, large windows, a sofa, two wicker chairs, and a small table with decorative items.

9. CAPTIVA~Adults Only, 2nd Floor King Room w/Community Pool at Azul Mansion!

CAPTIVA~Adults Only, 2nd Floor King Room w/Community Pool at Azul Mansion!
Old Town Key West
United States
Gabby R.
CAPTIVA~Adults Only, 2nd Floor King Room w/Community Pool at Azul Mansion!
A covered outdoor area with wicker furniture and a pool.
A beach with palm trees and a clear sky.
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.

10. 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
AED 764
AED 1,472 total
includes taxes & fees
2 Nov - 3 Nov
COHIBA~Adults Only, Poolview (2nd Floor) Queen Room in Historic Azul Mansion!
View all properties

Top Stock Island Hotel Reviews

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

8/10 Good
"It's okay to stay for few days"
Marcos 1-night trip
Posted 3 hours ago
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent
"Very cute and clean place to stay"
Angelica 3-night trip
Posted 4 hours ago
Winslow's Bungalows - Key West Historic Inns
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent
"We had a wonderful stay at casa marina. The rooms were clean, staff were super friendly and always so helpful, the entire resort felt like a dream. We can’t wait to be back!"
Rita 5-night trip
Posted 9 hours ago
Casa Marina Key West, Curio Collection by Hilton
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent
"The rooms were nice. The staff were friendly, but the back yard lounge/pool area was my favourite. Beautiful place to longe day or night. The free shuttle to Duval street runs every hour and made it so easy to enjoy downtown!"
Nicole 1-night trip
Posted 9 hours ago
DoubleTree Resort by Hilton Grand Key - Key West

Explore a world of travel with Expedia