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.
Questo complesso di appartamenti si trova a Key West, in Città Vecchia di Key West, e vanta una posizione strategica sul mare. Casa e Museo di Ernest Hemingway e Southernmost Point sono due delle principali attrazioni della zona. A livello naturalistico, invece, spiccano Spiagge delle Florida Keys e Fort Zachary Taylor Historic State Park. Anche Key West Butterfly and Nature Conservatory e Florida Keys Eco - Discovery Center meritano una visita. Scopri le tante discipline sportive della zona, tra cui immersioni subacquee, snorkeling e vela, oppure vivi all'avventura con fantastiche attività all'aperto come jogging e ciclismo. Vai alla guida turistica di Key West
Aeroporto Internazionale di Key West (EYW) - 12 min. in auto
Ristoranti
Circle K
1 min a piedi
Cuban Coffee Queen (Duval)
1 min a piedi
Southernmost Point Bar in the USA
4 min a piedi
Old Town Tavern
4 min a piedi
Banana Cafe
1 min a piedi
Domande frequenti
Gli animali sono accettati presso BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!?
No, questa struttura non accetta animali domestici.
Quanto costa il parcheggio presso BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!?
Presso la struttura è disponibile un parcheggio in loco.
A che ora si deve eseguire il check-in presso BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!?
Orario di inizio del check-in: 15:00.
A che ora si deve eseguire il check-out presso BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!?
Orario del check-out: 11:00.
Dove si trova BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!?
A pochi passi da luoghi d'interesse come City Zoo Gallery e Duval Street, questo condominio vanta una buona posizione in zona Città Vecchia di Key West. Spiagge delle Florida Keys e South Beach si trovano ugualmente a meno di 5 minuti di distanza.
Recensioni
Recensioni su BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!
9,8
Eccezionale
Tutte le recensioni mostrate sono state scritte da ospiti che hanno effettivamente soggiornato nella struttura. Solo i viaggiatori che hanno prenotato un soggiorno con noi possono inviare una recensione. Verifichiamo le recensioni seguendo le nostre linee guida e le pubblichiamo tutte, positive e negative.Maggiori informazioniApertura in un’altra finestra
10
Pulizia
10
Posizione
10
Personale e servizio
10
Condizioni e dotazioni della struttura
Valutazione di 10 - Eccellente. 9 su 10 recensioni
10 - Eccellente
9
Valutazione di 8 - Buono. 1 su 10 recensioni
8 - Buono
1
Valutazione di 6 - Soddisfacente. 0 su 10 recensioni
6 - Soddisfacente
0
Valutazione di 4 - Scarso. 0 su 10 recensioni
4 - Scarso
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Valutazione di 2 - Terribile. 0 su 10 recensioni
2 - Terribile
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Recensioni
Recensione verificata
10/10 Eccellente
Sarah
25 ago 2026
Mi è piaciuto: Pulizia, personale e servizio, servizi e condizioni e dotazioni della struttura
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.
Soggiorno di 4 notti ad agosto 2026
Recensione verificata
10/10 Eccellente
Kortnie H.
29 mag 2026
Mi è piaciuto: Pulizia, check-in, comunicazione, posizione e accuratezza dell’annuncio
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.
Soggiorno di 3 notti ad aprile 2026
Da un sito partner
10/10 Eccellente
Brandon V.
23 lug 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.
Da un sito partner
10/10 Eccellente
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.
Recensione verificata
10/10 Eccellente
Amanda S.
20 lug 2026
Soggiorno di 3 notti a giugno 2026
Recensione verificata
10/10 Eccellente
THOMAS H.
14 giu 2026
Mi è piaciuto: Pulizia, check-in, comunicazione e accuratezza dell’annuncio