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.
dit appartement ligt bij de zee in de wijk Oude stad van Key West in Key West. Museumhuis van Ernest Hemingway en Southernmost Point zijn noemenswaardige bezienswaardigheden en bij Stranden van Florida Keys en Historisch staatspark Fort Zachary Taylor kun je van het natuurschoon in de omgeving genieten. Vlinder- en natuurreservaat van Key West en Interactief milieucentrum Florida Keys zijn ook zeker het bezoeken waard. Geniet van wat tijd op of aan het water dankzij faciliteiten voor duiken, snorkelen en zeilen in de buurt, of ga lekker fietsen in de buitenlucht. Bekijk onze reisgids voor Key West
Zijn huisdieren welkom bij BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!?
Nee, huisdieren zijn bij deze accommodatie niet toegestaan.
Hoeveel kost een verblijf bij BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!?
Vandaag, 13 nov. 2026, kost een verblijf bij BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches! van één nacht voor twee volwassenen op 18 nov. 2026 min. € 320, inclusief belastingen en toeslagen. Deze prijs is gebaseerd op de laagste gevonden prijs per nacht in de afgelopen 24 uur voor verblijven in de komende 30 dagen. Prijzen kunnen wijzigen. Kies je datums voor meer accurate prijzen.
Wat kost het om bij BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches! te parkeren?
Je kunt ter plaatse parkeren bij de accommodatie.
Hoe laat kan ik inchecken bij BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!?
Je kunt vanaf 15.00 uur inchecken.
Tot hoe laat kan ik bij BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches! uitchecken?
Je dient uiterlijk om 11.00 uur uit te checken.
Waar ligt BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!?
Dit appartement ligt in Oude stad van Key West, vlak bij City Zoo Gallery en Duval Street. Ook Stranden van Florida Keys en South Beach liggen binnen 5 minuten lopen.
Beoordelingen
Beoordelingen over BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!
9,8
Uitzonderlijk
Alle weergegeven beoordelingen zijn gebaseerd op echte gastenervaringen. Alleen reizigers die een verblijf bij ons hebben geboekt, kunnen een beoordeling indienen. We verifiëren beoordelingen op basis van onze richtlijnen en plaatsen alle beoordelingen, of ze nu positief of negatief zijn.Meer informatieOpent in een nieuw venster
10
Netheid
10
Locatie
10
Personeel en service
10
Staat van de accommodatie en faciliteiten
Gastenscore: 10 - Uitstekend. 9 van 10 beoordelingen
10 - Uitstekend
9
Gastenscore: 8 - Goed. 1 van 10 beoordelingen
8 - Goed
1
Gastenscore: 6 - Redelijk. 0 van 10 beoordelingen
6 - Redelijk
0
Gastenscore: 4 - Matig. 0 van 10 beoordelingen
4 - Matig
0
Gastenscore: 2 - Ontzettend slecht. 0 van 10 beoordelingen
2 - Ontzettend slecht
0
Beoordelingen
Geverifieerde beoordeling
10/10 – Voortreffelijk
Sarah
25 aug 2026
Positief: Netheid, personeel en service, voorzieningen en staat van de accommodatie en faciliteiten
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.
4 nachten verbleven in augustus 2026
Geverifieerde beoordeling
10/10 – Voortreffelijk
Kortnie H.
29 mei 2026
Positief: Netheid, inchecken, communicatie, locatie en accuraatheid advertentie
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.
3 nachten verbleven in april 2026
Van een partnersite
10/10 – Voortreffelijk
Brandon V.
23 jul 2026
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.
Van een partnersite
10/10 – Voortreffelijk
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.
Geverifieerde beoordeling
10/10 – Voortreffelijk
Amanda S.
20 jul 2026
3 nachten verbleven in juni 2026
Geverifieerde beoordeling
10/10 – Voortreffelijk
THOMAS H.
14 jun 2026
Positief: Netheid, inchecken, communicatie en accuraatheid advertentie