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SMUGGLER'S COVE ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!

Photo gallery for SMUGGLER'S COVE ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!

A brick pathway leading to a white staircase with a covered area above. - SMUGGLER'S COVE ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches! (Key West)
A covered balcony with wicker chairs, a view of palm trees, and multiple flags. - SMUGGLER'S COVE ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches! (Key West)
A compact kitchen with a modern design, featuring a refrigerator, microwave, and wooden countertop. - SMUGGLER'S COVE ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches! (Key West)
A bar with a wooden bar counter, red stools, and shelves stocked with bottles. - SMUGGLER'S COVE ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches! (Key West)
A white building with a balcony, palm trees, and flags. - SMUGGLER'S COVE ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches! (Key West)
A short walk from Southernmost Point and Duval Street, SMUGGLER'S COVE ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches! has plenty to offer. Stay connected with free in-room WiFi.

Reviews

10 out of 10
Exceptional

Popular amenities

  • Free WiFi
  • Air conditioning
  • Parking available

Add dates for prices

About this property

SMUGGLER'S COVE ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!

  • PICTURESQUE LANDMARK GUESTHOUSE WITH CELEBRATED RUM BAR...
    Steeped in the rich 19th century lore of treasure hunts, romantic rum-running adventures, daring bootleggers, and notorious moonshiners and racketeers, the Smuggler's Cove room within the Speakeasy Inn is nestled in true Key West magic. This unique conch-style adult-only retreat is brimming with authentic stories of derring-do during Prohibition days. The inn was the home of Raul Vasquez, a cigar selector at the local Gato cigar factory, whose true passion was rum running between Key West and Cuba. He cut a colorful swath in this southernmost community, smuggling rum and storing it in his "secret cellar" - one of the few basements in Key West! You are right on Duval Street, renowned for its proliferation of whimsical art galleries, stellar restaurants and relaxing bars. Nestled in the heart of Old Town, you are only a couple blocks from the beach and the Southernmost Point.
    ***All guests must be 21 years of age or older as this is an adult only property AND the primary renter must be 25 years of age or older.

    DETAILS AND AMENITIES...
    On the first floor of the Speakeasy Inn resides the Rum Bar, which boasts an impressive selection of delicious rums from all over the globe. Join us for our rum tastings of both vintage and popular rums. Each guest room offers outdoor seating for its occupants. Amenities in the rooms include flat screen TVs, individually operated ACs, coffee makers, refrigerators, microwaves, and all rooms have private bathrooms with showers.

    SLEEPING ARRANGEMENTS...
    The Smuggler's Cove room is located downstairs and offers two queen beds and is also our ADA compliant room for our guests who require special consideration (roll in shower and grab bars). Enjoy a stocked kitchenette with a large sink, an ample shower bathroom and a hanging closet for your convenience.

    OUTDOOR LIVING...
    Take in the island air and sip on your frosted cocktail just outside of your room, with a round table and 4 cushioned chairs. Upstairs features our wraparound porch overlooking Duval Street, a favorite people-watching spot! It has been restored to perfection for the pleasure of our guests.

    PARKING...
    Parking is an additional $15/day plus tax and is limited, and not guaranteed. The lot is located 1/2 block away and an address will be provided upon payment. You may secure your space by requesting to add it to your reservation at any time but we suggest reserving in advance to guarantee availability. There are also some free spaces on street, as well as metered spaces in the surrounding area.

    PETS...
    This is not a pet-friendly inn.

    Cancellations requested at least 30 days prior to arrival receive a full refund.
    Cancellations requested at least 14 days prior to arrival receive a 50% refund.

    JOIN THE ADVENTURE...

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About the neighborhood

Located by the sea, this condo is in Old Town Key West, a neighborhood in Key West. Ernest Hemingway Home and Museum and Southernmost Point are notable landmarks, and the area's natural beauty can be seen at Florida Keys Beaches and Fort Zachary Taylor Historic State Park. Key West Butterfly and Nature Conservatory and Florida Keys Eco - Discovery Center are also worth visiting. Jet skiing, scuba diving, and snorkeling offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling nearby. Visit our Key West travel guide
View more Condo Rentals in Key West
Map
Key West, FL

What's nearby

  • A street with a pharmacy, a theater, and a yellow building.
    Duval Street
    1 min walk - 0.0 km
  • A wooden sign with information about South Beach, Key West, Florida, including public beach status, restaurant hours, and beach chair rental.
    South Beach
    3 min walk - 0.3 km
  • A building with a sign reading "The Key West Butterfly & Nature Conservatory".
    Key West Butterfly and Nature Conservatory
    3 min walk - 0.3 km
  • A two-story colonial-style building with a balcony, surrounded by lush greenery and palm trees.
    Ernest Hemingway Home and Museum
    4 min walk - 0.4 km
  • A colorful monument with text indicating it is the Southernmost Point of the Continental U.S.A. in Key West, Florida.
    Southernmost Point
    5 min walk - 0.4 km

Getting around

  • Key West Intl. Airport (EYW)
    12 min drive

Restaurants

  • Circle K
    1 min walk
  • Cuban Coffee Queen (Duval)
    1 min walk
  • Southernmost Point Bar in the USA
    4 min walk
  • Old Town Tavern
    4 min walk
  • Banana Cafe
    1 min walk

Frequently asked questions

Is SMUGGLER'S COVE ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches! pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at SMUGGLER'S COVE ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!?

Check-in begins at 3:00 PM.

What time is check-out at SMUGGLER'S COVE ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!?

Check-out is at 11:00 AM.

Where is SMUGGLER'S COVE ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches! located?

Located in Old Town Key West, this condo building is steps from City Zoo Gallery and Duval Street. Florida Keys Beaches and South Beach are also within 5 minutes.

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Reviews

SMUGGLER'S COVE ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches! Reviews

10

Exceptional

10

Cleanliness

10

Location

8.0

Staff & service

10

Property conditions & facilities
Rating 10 - Excellent. 20 out of 20 reviews
Rating 8 - Good. 0 out of 20 reviews
Rating 6 - Okay. 0 out of 20 reviews
Rating 4 - Poor. 0 out of 20 reviews
Rating 2 - Terrible. 0 out of 20 reviews

Reviews

From a partner site

10/10 Excellent

Excellent accomodations

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Everything was nice, no parking available, had to street park which was expensive.However did find out they had limited parking access somewhere.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location, super nice room......
Stayed 2 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Walking distance to any of the best spots in Key West! This stay was perfect for us and our friends to spend an incredible weekend in the Florida Keys.
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
An amazing location on a quiet portion of Duval Street. They thought of everything you could need in the room. Very spacious and comfortable. Super easy check in/out.
Stayed 2 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great property in a great location right on Duval next to an incredible Rum bar. Highly recommend
Stayed 1 night in Apr 2026
From a partner site

10/10 Excellent

Perfect ambiance and location

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Quaint and nicely appointed room, private with small patio. Couldn’t ask for nicer or more helpful workers at the Rum Bar.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing clean! Nice location! Super easy
Stayed 1 night in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The host contacted early to tell you the process and verify contact numbers. The room was really clean. I liked that it was on Duval street but on the quiet end. It was easy to get to places and then relax when you wanted to. The room was as described.
Stayed 4 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Location ideal for movement around tourist area. We sleep like babies in the quiet of room, walked out to street and it was active with happy tourist. Excellent!!! We replenished and discussed our days activities relaxing on deck areas with a refreshment from Rum Bar. Again, ideal!!! Speakeasy inn is a come back again resting area. Clean and safe!!!!
Stayed 6 nights in Jun 2026
From a partner site

10/10 Excellent

Favorite Stay in Key West to Date

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Our experience at the Speakeasy Inn was absolutely perfect! We love the south side of the island and this quaint little rental on Duval provides a great spot to call home while visiting Key West. Definitely will be back!
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This particular room hidden behind the rum saloon was delightful! Plenty of towels, a refrigerator large enough to hold our bottled waters and leftovers, a very comfortable bed, and a cute sitting area to watch critters peeping in or you watching people walking by. Theres a coffee shop conveniently across the street or you can walk down Duval to Circle K for cheap coffee or make it in your room with the Keurig. The short walk to the south point marker makes it very convenient!
Walkway to room.
Beginning of walkway from Duval. Hidden from public
Early morning view looking towards Southern point monument.
Short walk to point
Stayed 1 night in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Stayed 4 nights in Jun 2026
Verified review

10/10 Excellent

Stayed 1 night in Apr 2026