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 16 - Oct 17
Tomorrow
Oct 17 - Oct 18
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

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 living room with a sofa, armchair, coffee table, and a cabinet with decorative items.
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
￥33,434
￥81,560 total
includes taxes & fees
Oct 19 - Oct 20
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
A balcony with a view of a street, a bench, and a potted plant.
A hotel lobby with a bar area, seating, and a fireplace.
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.

2. Pegasus International Hotel

Pegasus International Hotel
Old Town Key West
United States
Karla
￥26,466
￥37,779 total
includes taxes & fees
Nov 3 - Nov 4
Pegasus International Hotel
A covered outdoor area with a table and chairs, surrounded by white railings and palm trees.
A beach with palm trees and a clear sky.
A wooden staircase with a view of greenery outside.
A large window with multiple panes overlooking a swimming pool and lush greenery.

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.
￥18,021
￥44,718 total
includes taxes & fees
Oct 19 - Oct 20
CORONA ~ Adults Only, 2nd Floor King Room w/ Community Pool at Azul Mansion!
A wooden boardwalk leading to a beach with palm trees and a clear sky.
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.
A large white building with a balcony, palm trees, and a brick pathway leading to the entrance.

4. Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn
Key West Historic District
United States
chris
￥37,689
￥42,400 total
includes taxes & fees
Oct 28 - Oct 29
Amsterdam's Curry Mansion Inn
A living room with two sofas, a coffee table, and a window with blinds.
A covered outdoor deck with wicker furniture and a white railing.
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.

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.
￥20,869
￥48,399 total
includes taxes & fees
Oct 25 - Oct 26
HAVANA VIEJA ~ Adults Only, First Floor Queen Room w/ Community Pool!
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 beach with palm trees and a clear sky.
A wooden staircase with a view of greenery outside.

6. 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.
￥18,021
￥44,718 total
includes taxes & fees
Oct 19 - Oct 20
FLOR DE CANA ~ Adults-Only 2nd Floor Queen Room w/Pool View at Azul Mansion!
A covered outdoor deck with wicker furniture and a white railing.
A beach with palm trees and a clear sky.
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 wooden staircase with a view of greenery outside.

7. 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.
￥20,392
￥47,702 total
includes taxes & fees
Oct 25 - Oct 26
CLARO ~ Adults Only, Pool View (2nd Floor) King Room in Azul Mansion!
A covered outdoor deck with wicker furniture and a white railing.
A spacious room with a ceiling fan, large windows, a sofa, two wicker chairs, and a small table with decorative items.
A beach with palm trees and a clear sky.
A two-story white building with a balcony, surrounded by greenery and a white picket fence.

8. 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.
￥21,660
￥49,290 total
includes taxes & fees
Oct 26 - Oct 27
CAPTIVA~Adults Only, 2nd Floor King Room w/Community Pool 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.
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.
A kitchen with a built-in oven, a toaster, and a coffee maker.

9. Studio Blu - Historic Key West Studio + Bikes

Studio Blu - Historic Key West Studio + Bikes
Old Town Key West
United States
Emily F.
￥33,090
￥66,002 total
includes taxes & fees
Nov 3 - Nov 4
Studio Blu - Historic Key West Studio + Bikes
A covered outdoor deck with wicker furniture and a white railing.
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.
A pool area with lounge chairs, a pool with clear blue water, and a covered patio with outdoor seating.

10. ARIA~Adult Only, Treetop King Suite w/ Balcony & Community Pool!

ARIA~Adult Only, Treetop King Suite w/ Balcony & Community Pool!
Old Town Key West
United States
Rob G.
￥23,715
￥51,917 total
includes taxes & fees
Oct 18 - Oct 19
ARIA~Adult Only, Treetop King Suite w/ Balcony & Community Pool!
View all properties

Top Stock Island Hotel Reviews

The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

10/10 Excellent
"We enjoyed the King Suite. Especially the modern updated ensuite. The pool and hot tub were fantastic in a unique private setting with ample palm trees and greenery."
Camiel 3-night trip
Posted 6 hours ago
The Southernmost Inn - Adults Only
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent
"Amazing stay! Would highly recommend!"
Courtney 1-night trip
Posted 7 hours ago
Winslow's Bungalows - Key West Historic Inns
Fairfield by Marriott Inn & Suites Key West at The Keys Collection

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

10/10 Excellent
"Unable to understand with the staff on my arrival. It was so frustrating!! Other than that nice atmosphere."
Brigida 2-night trip
Posted 8 hours ago
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

8/10 Good
"Pretty spot with shuttle service to town. Pools are nice, but no beach access. Restaurant was being remodeled, and a food truck was on-site all day with breakfast and lunch or light dinner options. Super friendly and helpful staff!"
Judy 5-night trip
Posted 11 hours ago
Parrot Key Hotel & Villas
Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"We were very happy with how nice, clean and comfortable our 1 bedroom was. The staff was very helpful via text messages for anything we needed like coffee. The pool was clean and well kept. The shuttle bus to Duval street was a very pleasant surprise and the drivers were really prompt."
Rebecca 3-night trip
Posted 12 hours ago
Beachside Resort & Residences
Pier House Resort & Spa

Pier House Resort & Spa

8/10 Good
"The location of the property was great for our visit because we had a couple of excursions from the pier not too far. The property was really nice and we enjoyed having the beach to be able to get in the ocean after a hot day. Food and drinks at the hotel were great. The only complaint I have is in our room there was only 1 tabletop lamp and only one in the sitting area so it was real hard to see when trying to get ready with 4 people. Even the bathroom light wasn’t very bright. I would stay here again."
Robin 4-night trip
Posted 13 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
"Great property"
Charlene 3-night trip
Posted 14 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
"Beautiful resort. Very good restaurant on site. Shuttle bus to and from Old Town Key West every hour. The staff was exceptional. Highly recommend this resort."
William 1-night trip
Posted 2 days ago
DoubleTree Resort by Hilton Grand Key - Key West

Explore a world of travel with Expedia