Condo

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 white building with a balcony, palm trees, and flags.
A brick pathway leading to a white staircase with a covered area above.
A two-story building with a balcony, palm trees, and flags.
A hotel room with two beds, a ceiling fan, a nightstand with a lamp, and a painting on the wall.
A bedroom with two beds, a ceiling fan, a nightstand with a lamp, and a window with curtains.

Reviews

10 out of 10
Exceptional

Highlights

  • Discover nearby landmarks
    Walk to Duval Street
1 bedroom1 bathroomSleeps 4

Popular amenities

  • Air-conditioning
  • Refrigerator
  • Onsite parking available
  • Internet
  • Laundry room
  • Non-smoking

Explore the area

View map
Key West, FL
  • Place, Duval Street
    ‪1 min walk‬
  • Place, South Beach
    ‪3 min walk‬
  • Place, Southernmost Point
    ‪5 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪9 min drive‬

Rooms & beds

1 bedroom (sleeps 4)

Bedroom 1

2 Queen Beds

1 bathroom

Bathroom 1

Toilet · Shower only

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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House Rules

Check in after 3:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Adults only
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property # 5092063vb
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.
Map
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 27 October 2026 start from NZ$552, 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.
Learn moreOpens in a new window
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

10/10

Cleanliness

8.0/10

Staff & service

10/10

Amenities

10/10

Property conditions & facilities

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Perfect location
Stayed 4 nights in Aug 2026
Response from Management on 19 October 2026
We are so happy you found this property and its location ideal for your get away in paradise. We hope you'll stay with us again next time you visit!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location, super nice room......
Stayed 2 nights in Jun 2026
Response from VrboOwner on 22 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.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful stay! Recommend this to anyone.
Stayed 7 nights in Aug 2026
Response from VrboOwner on 27 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.
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
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

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.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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

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.
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
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

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.
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
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

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.
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
Response from VrboOwner on 23 March 2026
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.
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
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

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.
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
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

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.
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
Response from VrboOwner on 5 August 2026
We so appreciate the excellent rating, thank you! We hope your travels will bring you back as our guest soon!
Verified review

10/10 Excellent

Stayed 1 night in Apr 2026

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