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SMUGGLER'S COVE @ Speakeasy Inn Key West!
Capacity
1 Bedroom
1 Bath
Sleeps 4
About
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 limited and not guaranteed, offered on a first come first serve basis at an additional fee of $15 per night. There are also some free as well as metered on street parking spaces on the surrounding streets. Most guests walk or bike ride to all of the nearby attractions once they secure a parking space.
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...
Features
Amenities
- Television
- Air Conditioning
- Hair Dryer
- Parking
- Free Wifi
- Coffee Maker
- Dishes & Utensils
- Microwave
- Refrigerator
- pets not allowed
- Kitchenette
- Ironing Board
- High Speed Internet
- Cable TV
Location
- Speakeasy Inn
Availability
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Map
Reviews
A great weekend in a beautiful location
July 2026
Aaron B., Miramar, FL US
Aaron B., Miramar, FL US
Overall
Property condition
Location
Cleanliness
Services from rental manager
Great location
July 2026
Recent Guest, Seymour, IN US
Recent Guest, Seymour, IN US
Overall
Property condition
Location
Cleanliness
Services from rental manager
The room was comfortable and clean. The host communicated well and checkin and check out were really easy. The location is right on Duval Street. It is a few blocks from the buoy marking southernmost point. You are about a half mile walk to most of Duval Street's other attractions. This meant you could retreat to your room easily if the atmosphere gets to be too much. The Rum Bar attached to the room was a laid back place that welcomed guests. The hosts provided materials to help guests find things to do. They even seemed to think of items you might not have thought of. There were two folding chairs,beach towels, and robes in the bathroom closet. We did not use these but it illustrates the details the hosts went to for guests. One item to make sure you know. The door to the unit is a glass door. While the walkway was limited to the guests in other units it did require that the curtains be closed for privacy most of the time. The grounds were lovely. There was a sitting areas right outside the room. If we return to Key West we would return to this rental.
Manager's Response
Thanks so much for the lovely feedback! We’re happy to hear you enjoyed the property and would love to host you again in the future.
Great!
July 2026
Recent Guest, Dunedin, FL US
Recent Guest, Dunedin, FL US
Overall
Property condition
Location
Cleanliness
Services from rental manager
The stay was perfect! This was right on Duval St. as advertised and every time we stepped outside we were right in the heart of Key West. The RumBar attached to the front was a great time but a little overpriced. Other than that this was exactly what we were looking for!
Manager's Response
We’re grateful for your glowing review! It was such a pleasure to host you, and we’re already looking forward to your return to the island.
Excellent accomodations
July 2026
Shane B., Smyrna, TN US
Shane B., Smyrna, TN US
Overall
Property condition
Location
Cleanliness
Services from rental manager
Everything was nice, no parking available, had to street park which was expensive.However did find out they had limited parking access somewhere.
Manager's Response
So glad to hear you had a positive experience! We’d love nothing more than to welcome you back for another wonderful stay.
Perfect ambiance and location
June 2026
robin r., Glen Allen, VA US
robin r., Glen Allen, VA US
Overall
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Location
Cleanliness
Services from rental manager
Quaint and nicely appointed room, private with small patio. Couldn’t ask for nicer or more helpful workers at the Rum Bar.
Manager's Response
Thank you for the kind words Robin! We’re so happy you enjoyed your stay in paradise and we’d be thrilled to welcome you back for another unforgettable visit.
Favorite Stay in Key West to Date
May 2026
Matt L., Canton, MI US
Matt L., Canton, MI US
Overall
Property condition
Location
Cleanliness
Services from rental manager
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!
Manager's Response
What a joy to read your review - thank you so much Matt! We’re so glad you loved your time in paradise and can’t wait to have you back on the island soon.
Wonderful room in a great location, the area was quiet but close to the excitement. Walking distance to great locations.
Manager's Response
Thank you for the kind words! We’re so happy you enjoyed your stay in paradise and we’d be thrilled to welcome you back for another unforgettable visit.