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

Find Historic Hotels in Stock Island, FL

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Check availability on Stock Island Historic Hotels

Tonight
3 Sep - 4 Sep
Tomorrow
4 Sep - 5 Sep
This weekend
4 Sep - 6 Sep
Next weekend
11 Sep - 13 Sep

Our top choices for Stock Island historic hotels

1. Pegasus International Hotel

Pegasus International Hotel
Old Town Key West
Canada
Shahid
AED 465
AED 709 total
includes taxes & fees
11 Sep - 12 Sep
Pegasus International Hotel

2. Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn
Key West Historic District
United States
Melissa
AED 427
AED 481 total
includes taxes & fees
9 Sep - 10 Sep
Amsterdam's Curry Mansion Inn

3. HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Community Pool!

HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Community Pool!
Old Town Key West
United States
JUANITA R.
AED 400
AED 1,015 total
includes taxes & fees
16 Sep - 17 Sep
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Community Pool!

4. 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.
AED 535
AED 1,223 total
includes taxes & fees
7 Sep - 8 Sep
Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!

5. 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
Brandon I.
AED 360
AED 962 total
includes taxes & fees
6 Sep - 7 Sep
CLARO ~ Adults Only, Pool View King Room in Azul Mansion!

6. COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!
Old Town Key West
United States
Christina
AED 360
AED 966 total
includes taxes & fees
7 Sep - 8 Sep
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

7. FONTANA ~ Adults Only, Poolside King Room at Azul Mansion!

FONTANA ~ Adults Only, Poolside King Room at Azul Mansion!
Old Town Key West
United States
Jessica S.
AED 360
AED 966 total
includes taxes & fees
8 Sep - 9 Sep
FONTANA ~ Adults Only, Poolside King Room at Azul Mansion!

8. 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
AED 360
AED 966 total
includes taxes & fees
8 Sep - 9 Sep
CORONA ~ Adults Only, King Room with Community Pool at Azul Mansion!

9. FLOR DE CANA ~ Adults Only, Queen Room w/Pool View at Azul Mansion!

FLOR DE CANA ~ Adults Only, Queen Room w/Pool View at Azul Mansion!
Old Town Key West
United States
Jake H.
AED 360
AED 962 total
includes taxes & fees
6 Sep - 7 Sep
FLOR DE CANA ~ Adults Only, Queen Room w/Pool View at Azul Mansion!

10. 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.
AED 419
AED 1,039 total
includes taxes & fees
23 Sep - 24 Sep
CORTEZ ~ Adults Only, King Room w/Pool View at Azul Mansion!
View all properties

Top Stock Island Hotel Reviews

Southwinds Motel

Southwinds Motel

10/10 Excellent
"Southwinds Motel has to be the absolute best spot I’ve stayed at when it comes to conveniences on site along with an awesome location and proximity to sites and activities. Perfectly located around the Southernmost part of Key West, Southwinds gives you fully stocked bar WITH a built-in liquor store. Super convenient off rip. Bar has live music in the afternoon and evening, a pretty nice pool and deck area and, what I really found most convenient, access to rentals for any means of transportation you need for Key West from bicycles to scooters to full sized golf carts. Rentals are provided by Bone Island rentals who also deliver your mode of moving around to the property and picks it up from the property. A totally ‘Key West’ luxury in my mind. So you’re not staying in the fanciest of shindigs, but you rented a motel because you probably plan to be out and about in beautiful Key West and not cooped up, so you most definitely shouldn’t have grand expectations, but you definitely won’t be disappointed with the digs either. Another thing I really appreciated was after check-in, we were also gifted 2 vouchers for free specialty cocktails from their bar. It was small drinks and only their specialty drinks but still complimentary, so we say thank you and enjoy. They let us combine both tickets for one full sized rum runner my wife enjoyed. Overall 10/10 for comfort, convenience, location and it’s vibe. Will absolutely be going back and 100 percent recommend to all staying in KW"
Juan 4-night trip
Posted 5 hours ago
Southwinds Motel
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

10/10 Excellent
"Nice"
Kenneth 1-night trip
Posted 13 hours ago
Hilton Garden Inn Key West / The Keys Collection
Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

10/10 Excellent
"The staff were outstanding, especially Anna at the front desk. They all were so warm and welcoming. The rooms were spacious and clean. The pool was clean and mostly quiet (which was nice and relaxing)."
sharon 3-night trip
Posted 18 hours ago
Hyatt Centric Key West Resort and Spa
Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"Great location. Nice amenities. Overall, a great place to stay."
Elizabeth 4-night trip
Posted 18 hours ago
Pier House Resort & Spa
Beachside Resort & Residences

Beachside Resort & Residences

8/10 Good
"Hot tub wasn’t working. It was just warm water. Gym was very hot. Beach wasn’t great. Elevator in my building wasn’t working g but you can use the one from the building next to it and walk over. So not that bad. Pool was great. Never crowded. Room was excellent. We had a suite with pool access. There was plenty of parking at the hotel and no charge to park We would still go back again."
Jose 8-night trip
Posted 2 days ago
Beachside Resort & Residences
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

8/10 Good
"My husband and I joined the hotel. I would definitely recommend this place. I felt like I was in a mini resort."
Quantona 3-night trip
Posted 3 days ago
DoubleTree Resort by Hilton Grand Key - Key West

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