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
18 Sep - 19 Sep
Tomorrow
19 Sep - 20 Sep
This weekend
18 Sep - 20 Sep
Next weekend
25 Sep - 27 Sep

Our top choices for Stock Island historic hotels

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 912
AED 2,066 total
includes taxes & fees
21 Sep - 22 Sep
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS

2. Pegasus International Hotel

Pegasus International Hotel
Old Town Key West
Canada
Shahid
AED 395
AED 630 total
includes taxes & fees
1 Oct - 2 Oct
Pegasus International Hotel

3. Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn
Key West Historic District
United States
Melissa
AED 524
AED 589 total
includes taxes & fees
22 Sep - 23 Sep
Amsterdam's Curry Mansion Inn

4. 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.
AED 400
AED 1,015 total
includes taxes & fees
23 Sep - 24 Sep
CORTEZ ~ Adults Only, 2nd Floor King Room w/Pool View at Azul Mansion!

5. 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
Christina
COHIBA~Adults Only, Poolview (2nd Floor) Queen Room in Historic Azul Mansion!

6. 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.
AED 841
AED 1,569 total
includes taxes & fees
19 Oct - 20 Oct
FUENTE ~ Adults Only, 2nd Floor, Pool View, King Room at Azul Mansion!

7. 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
Warren K.
CAPTIVA~Adults Only, 2nd Floor King Room w/Community Pool at Azul Mansion!

8. Studio Blu - Historic Key West Studio + Bikes

Studio Blu - Historic Key West Studio + Bikes
Old Town Key West
United States
Emily F.
AED 596
AED 1,302 total
includes taxes & fees
21 Sep - 22 Sep
Studio Blu - Historic Key West Studio + Bikes

9. 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
JUANITA R.
AED 360
AED 966 total
includes taxes & fees
20 Sep - 21 Sep
HAVANA VIEJA ~ Adults Only, First Floor Queen Room w/ Community Pool!

10. 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
Brandon I.
AED 400
AED 1,015 total
includes taxes & fees
30 Sep - 1 Oct
CLARO ~ Adults Only, Pool View (2nd Floor) King Room in Azul Mansion!
View all properties

Top Stock Island Hotel Reviews

Beachside Resort & Residences

Beachside Resort & Residences

8/10 Good
"The staff was very helpful. I had absolutely no problem with my suite. It was a very well furnished, one bedroom apartment. The the problem I guess, would be that the outside hot tub at the pool had not been working for months. The elevators were being repaired on the side where I was at the restaurant there. To me was overpriced, and not a lot to choose from. The outside bar, the staff really didn't either know how to make certain drinks, or they didn't have the ingredients to make certain drinks. And the food was so so they only had one Van. That brought you to and from downtown. And they stated that they had 2 more vans, but they've been broke for a very long time, because they can't get parts. Well, how about management getting involved? And going as high up as it takes to get the type of vans that you need and to get the place maintained and staffed properly. There was no pool person, and you had to go inside to get your towels, and it got a little messy at the pool area...And then I heard that there's some people that did have some issues with a room, but those problems were fixed within a day. So, I had wished that the Van would have offered rides to the airport, which was just a 12 minute ride down the street. If that.... the extra excursions they offered did not work out because they didn't have enough people to go on the boat they had. So you had to seek out other sailboats or boats in the area to do things. And if they were no"
Maria 4-night trip
Posted 16 hours ago
Beachside Resort & Residences
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

10/10 Excellent
"Excellent relaxing destination"
Menwoe 5-night trip
Posted 18 hours ago
Blue Flamingo Resort Key West
Hampton Inn Key West FL

Hampton Inn Key West FL

10/10 Excellent
"Clean room great staff"
Diana 2-night trip
Posted 23 hours ago
Hampton Inn Key West FL
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

10/10 Excellent
"This is the second year we have stayed here for our annual girl's trip. Everything was as great as it was last year. We plan on staying again next year."
Amanda 7-night trip
Posted 1 day ago
Hyatt Vacation Club at Windward Pointe, Key West
Southwinds Motel

Southwinds Motel

10/10 Excellent
"Second time staying at this hotel and will be back ASAP"
Susan 4-night trip
Posted 2 days ago
Southwinds Motel
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

10/10 Excellent
"Our stay was pleasant except for the rooster in the Palm tree that woke me up at 3;45 AM in the morning."
James 4-night trip
Posted 2 days ago
Hilton Garden Inn Key West / The Keys Collection

Explore a world of travel with Expedia