A short walk from Southernmost Point and Duval Street, BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches! has plenty to offer. Stay connected with free in-room WiFi.
Reviews
1010 out of 10
Exceptional
Entire condo
1 bedroom1 bathroom190 sq ft
Popular amenities
Free Wi-Fi
Air-conditioning
Parking available
The current price is HK$855
HK$855
HK$2,144 total
includes taxes & fees
21 Sept - 22 Sept
Add dates for prices
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...
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)
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
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
About the area
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. Visit our Key West travel guide
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 18 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 21 Sept 2026 start from HK$855, excluding 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 South Beach are also within 5 minutes.
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BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches! Reviews
Reviews
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.
The room was so perfect! Perfectly nestled just down a brick sidewalk right on Duval st. Closer to Southern most point, nice walking distance to Mallory square. The room was perfect for us.
Stayed 4 nights in Aug 2026
From a partner site
10/10 Excellent
Debbie M.
13 Feb 2026
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.
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.