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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 white building with a balcony, palm trees, and flags.
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 covered balcony with wicker chairs, a view of palm trees, and multiple flags.

Reviews

10 out of 10
Exceptional

Entire condo

1 bedroom1 bathroom18 sq m

Popular amenities

  • Free Wi-Fi
  • Air-conditioning
  • Parking available

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

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About the area

Key West

This condo places you in the centre of Key West, steps from Duval Street and within a short 5-minute stroll of Florida Keys Beaches. .Condo features free WiFi, a TV and a coffee/tea maker. A fridge and a microwave make in-room dining convenient. A hairdryer and an iron/ironing board are also available.
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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

About this property

Entire place

You'll have the entire condo to yourself and will only share it with other guests in your party.

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...

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Property amenities

Internet

  • Available in the condo: Free WiFi

Parking and transport

  • Parking on site

Food and drink

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Ice maker
  • Microwave
  • Refrigerator

Bedrooms

  • Bedroom
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Hair dryer
  • Shower

Entertainment

  • TV with cable/satellite channels

Laundry

  • Coin laundry

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city centre
  • Near a hospital
  • Near the marina
  • Near the sea

Things to do

  • Basketball nearby
  • Birdwatching nearby
  • Cycling nearby
  • Fishing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkelling nearby
  • Swimming nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

General

  • Property does not allow children
  • Unit size: 190 square feet

Policies

Check-in

Check-in time starts at 3:00 PM
Minimum check-in age - 25

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

  • No pets allowed

Children and extra beds

  • This property does not allow children.

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. On-site parties or group events are strictly prohibited. For guests' safety, the property includes a fire extinguisher, a smoke detector and a deadbolt lock in all accommodation.

Property is also known as

2731-280043

Frequently asked questions

Are there any beaches close to BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!?

Yep, BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches! is a short 4-minute walk from Florida Keys Beaches. Fun beach activities include snorkelling, scuba diving and sailing.

Does BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches! have a pool?

No, this condo doesn't have a pool.

Is there a free airport shuttle available at BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!?

No, BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches! does not offer an airport shuttle service.

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

Check-in begins at 3:00 PM. Check-out time is 11:00 AM.

Are pets allowed at BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!?

No, pets are not allowed.

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

Reviews

10

Exceptional

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

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.
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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Stayed 4 nights in May 2026