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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Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
About the area
Key West
Located by the sea, this condo is in Old Town Key West, a neighbourhood 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 snorkelling offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling nearby.
Key West, FL
What's nearby
Duval Street - 1 min walk - 0.0 km
South Beach - 3 min walk - 0.3 km
Key West Butterfly and Nature Conservatory - 3 min walk - 0.3 km
Ernest Hemingway Home and Museum - 4 min walk - 0.4 km
Southernmost Point - 5 min walk - 0.4 km
Getting around
Key West, FL (EYW-Key West Intl.) - 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 does it cost to stay at SMUGGLER'S COVE ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!?
As of 21 October 2026, prices found for a 1-night stay for 2 adults at SMUGGLER'S COVE ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches! on 14 September 2027 start from NZ$562, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at SMUGGLER'S COVE ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!?
On-site 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!?
Checkout 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 away from City Zoo Gallery and Duval Street. Florida Keys Beaches and South Beach are also within 5 minutes.
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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.
The location was perfect for our girls trip. Check in/out was really easy and the ladies I travelled with said this place was well worth the money. Would 100% stay here again.
Stayed 2 nights in Aug 2026
Response from VrboOwner on 3 September 2026
So glad to hear you had such a positive experience! We’d love nothing more than to welcome you back for another wonderful stay.
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
Response from VrboOwner on 30 July 2026
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.
From a partner site
10/10 Excellent
Gerald W.
26 September 2026
First visit to Key West
Rating Details:
The property manager was more than 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:
We had a great stay at the Speakeasy Inn. Beautiful place and GREAT location. Highly recommend staying there.
Response from VrboOwner on 29 September 2026
We truly appreciate your review! It makes us happy to know you loved this property, and we’d be delighted to host you again anytime.
Easy check in and check out. Also super easy to access and close to lots of shops and restaurants! We had a slight issue and the host resolved it super fast.
Stayed 2 nights in Jul 2026
Response from VrboOwner on 24 August 2026
We truly appreciate your review! It makes us happy to know you loved this property, and we’d be delighted to host you again anytime.
From a partner site
10/10 Excellent
Steve S.
9 October 2026
great place to stay
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:
Hate to give a great review because I don't want to many people knowing about it and it not having availability. But it was a great place to stay, very clean and comfortable. And such an easy check in process.
Response from VrboOwner on 11 October 2026
What a joy to read your review - thank you so much! We’re so glad you loved your time in paradise and can’t wait to have you back on the island soon.
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
Response from VrboOwner on 8 July 2026
Thank you for the kind words Nikola! We’re so happy you enjoyed your stay in paradise and we’d be thrilled to welcome you back for another unforgettable visit.
From a partner site
10/10 Excellent
Aaron B.
17 August 2026
A great weekend in a beautiful 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:
Wonderful room in a great location, the area was quiet but close to the excitement. Walking distance to great locations.
Response from VrboOwner on 18 August 2026
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.
Great property in a great location right on Duval next to an incredible Rum bar. Highly recommend
Stayed 1 night in Apr 2026
Response from VrboOwner on 26 May 2026
We’re so glad you had a great time with us Darren. It was truly a pleasure having you! We’d be delighted to welcome you back the next time your travels bring you to paradise.
From a partner site
10/10 Excellent
robin r.
8 July 2026
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.
Response from VrboOwner on 9 July 2026
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.
Your kind words mean the world to us Karen! Hosting you was an honor, and we can’t wait for the chance to welcome you back to our little slice of paradise.
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
Response from VrboOwner on 3 August 2026
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.
From a partner site
10/10 Excellent
Shane B.
25 July 2026
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.
Response from VrboOwner on 29 July 2026
So glad to hear you had a positive experience! We’d love nothing more than to welcome you back for another wonderful stay.
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
Response from VrboOwner on 28 July 2026
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.
From a partner site
10/10 Excellent
Matt L.
1 June 2026
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!
Response from VrboOwner on 3 June 2026
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.
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!