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!





Reviews
1010 out of 10
Exceptional
Popular amenities
- Free Wi-Fi
- Air-conditioning
- Parking available
Explore the area

Key West, FL
- Duval StreetPlace, Duval Street1 min walk
- South BeachPlace, South Beach3 min walk
- Southernmost PointPlace, Southernmost Point5 min walk
- Key West, FL (EYW-Key West Intl.)Airport, Key West, FL (EYW-Key West Intl.)12 min drive
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About the area
Key West
With a stay at this guesthouse, you'll be centrally located in Key West, steps from Duval Street and 4 minutes by foot from Florida Keys Beaches. .This guesthouse is 0.2 mi (0.4 km) from South Beach and 0.3 mi (0.4 km) from Ernest Hemingway Home and Museum.
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 Intl. Airport (EYW) - 12 min drive
Restaurants
- Circle K - 1 min walk
- Banana Cafe - 1 min walk
- Cuban Coffee Queen (Duval) - 1 min walk
- Rum Bar at the Speakeasy Inn - 1 min walk
- La Te Da - 1 min walk
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 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...
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 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...
Complimentary wireless internet access is available to keep you connected. The bathroom has a shower and a hair dryer. Conveniences include a refrigerator and a microwave.
This smoke-free guesthouse features a tennis court on site, snorkeling nearby, and sailing nearby. Recreational activities include scuba diving nearby.
Guests will find features like internet access and onsite parking.
Property amenities
Internet
- Available in all rooms: Free WiFi
- Available in some public areas: Internet access
Things to do
- Tennis
More
- Smoke-free property
Room amenities
Bedroom
- Bedsheets provided
Bathroom
- Hair dryer
- Shower
Entertainment
- TV with cable/satellite channels
Food and drink
- Coffee/tea maker
- Cookware, dishware, and utensils
- Ice maker
- Microwave
- Refrigerator
More
- Air conditioning
- Iron/ironing board
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
Pets not allowed
Children and extra beds
This property does not allow children
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
Onsite parties or group events are strictly prohibited
Safety features at this property include a fire extinguisher, a smoke detector, and a deadbolt lock
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
Property is also known as
2731-280043
BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches! Reviews
Reviews
10
Exceptional
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 1 out of 1 reviews
10 - Excellent
1
Rating 8 - Good. 0 out of 1 reviews
8 - Good
0
Rating 6 - Okay. 0 out of 1 reviews
6 - Okay
0
Rating 4 - Poor. 0 out of 1 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 1 reviews
2 - Terrible
0