Condo

BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!

Photo gallery for BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!

A brick pathway leading to a white staircase with a covered area above.
A bedroom with a bed, two bedside lamps, a ceiling fan, and three large wall-mounted pictures.
A bar area with a wooden bar counter, multiple stools, and a variety of bottles and glasses.
A white building with a balcony, palm trees, and flags.
A covered balcony with wicker chairs, a view of palm trees, and multiple flags.

Reviews

10 out of 10
Exceptional

Highlights

  • Discover nearby landmarks
    Near Duval Street
1 bedroom1 bathroomSleeps 2

Popular amenities

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

Explore the area

View in a 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 2)

Bedroom 1

1 Queen Bed

1 bathroom

Bathroom 1

Toilet · Shower only

About this property

BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby 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 Bootlegger Bay 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! The Inn's tropical decor features hand-crafted beds and tables made from original 1876 Dade County pine, reflecting a respectful nod to its most illustrious history. 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 Bootlegger Bay room is located downstairs and offers a queen bed. Enjoy a stocked kitchenette, a shower bathroom and a clothing hanging bar for your convenience.

OUTDOOR LIVING...
Take in the island air and sip on your frosted cocktail just outside of your room, with cushioned seating for your enjoyment. 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...
Our prices include all fees. No hidden fees.

Add dates for prices

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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 # 5092064vb
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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. Discover the area's water adventures with scuba diving, snorkelling and sailing nearby, or enjoy the great outdoors with cycling.
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 BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches! pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!?

As of 25 Sept 2026, prices found for a 1-night stay for 2 adults at BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches! on 2 Jan 2027 start from £499, 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 BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!?

On-site parking is available at the property.

What time is check-in at BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!?

Check-in begins at 3:00 PM.

What time is check-out at BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!?

Checkout is at 11:00 AM.

Where is BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby 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 Ernest Hemingway Home and Museum are also within 10 minutes.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 7 out of 7 reviews
Rating 8 - Good. 0 out of 7 reviews
Rating 6 - Okay. 0 out of 7 reviews
Rating 4 - Poor. 0 out of 7 reviews
Rating 2 - Terrible. 0 out of 7 reviews

10/10

Cleanliness

10/10

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

From a partner site

10/10 Excellent

In the middle of all the action!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Very good experience. The owners/management company was wonderful! Could walk to everythin, including the ferry that goes to Dry Torgogus, as well as the airport.
Response from VrboOwner on 14 Feb 2026
It makes us so happy to know you had a great time as our guest Debbie! We loved having you as our treasured guest and hope to see you again!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Friendly people, our room was clean and so homey (room 2 - second floor). No noise from bar on first floor. We walked to most everything, some things we did use uber. It was hot - August, so uber to restaurant at the wharf and walked back.
Stayed 4 nights in Aug 2026
From a partner site

10/10 Excellent

Cozy spot to rest

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: Comfortable bed, clean space, well equipped kitchenette & COLD AC. This particular room is small and without any seating, but a very comfortable place to clean up & rest after long days exploring Key West. Very convenient Duval St location on the quiet end, but just a few blocks from the action.
Response from VrboOwner on 29 Jul 2026
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.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent stay! The property was exactly what we were looking for. The location was perfect—within walking distance of great restaurants, bars, and nightlife, making it easy to enjoy the area without needing to drive.. The attached bar gives the property a good vibe. The accommodations were comfortable, clean, and well-maintained. We had a wonderful stay and would definitely book this property again.
Stayed 3 nights in Apr 2026
Response from VrboOwner on 17 Jun 2026
We’re so glad you had a great time with us Kortnie. It was truly a pleasure having you! We’d be delighted to welcome you back the next time your travels bring you to paradise.
Verified review

10/10 Excellent

Stayed 3 nights in Jun 2026
Response from VrboOwner on 3 Aug 2026
Thank you for the excellent rating! We are delighted you had a great experience and look forward to welcoming you back!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Stayed 4 nights in May 2026
Response from VrboOwner on 30 Jun 2026
Thank you for the excellent rating Thomas! We appreciate it and hope you'll return soon as our guest!

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