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.
Este condominio se encuentra junto al mar, en Centro histórico de Key West, Key West. Casa y museo de Ernest Hemingway y Southernmost Point son lugares emblemáticos, y la belleza natural de la zona puede apreciarse en Playas de los Cayos de la Florida y Parque histórico estatal Fort Zachary Taylor. También vale la pena conocer Centro de Conservación de las Mariposas y la Naturaleza de Cayo Hueso (Key West) y Florida Keys Eco - Discovery Center. En la zona puedes practicar actividades como buceo, snorkel y paseos en velero, o disfrutar del aire libre mientras haces ciclismo. Visita nuestra guía de Key West
Key West, FL (EYW-A. Internacional de Key West) - 12 min en auto
Restaurantes
Circle K
A 1 min a pie
Cuban Coffee Queen (Duval)
A 1 min a pie
Southernmost Point Bar in the USA
A 4 min a pie
Old Town Tavern
A 4 min a pie
Banana Cafe
A 1 min a pie
Preguntas frecuentes
¿BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches! acepta mascotas?
No, la propiedad no acepta mascotas.
¿Cuánto cuesta hospedarse en BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!?
Al 13 nov. 2026, los precios encontrados para una estancia de 1 noche para 2 adultos en BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches! el 18 nov. 2026 serán a partir de $3,458 MXN, sin impuestos y cargos incluidos. Este precio es con base en el precio por noche más bajo encontrado en las últimas 24 horas para estancias en los próximos 30 días. Los precios están sujetos a cambios. Elige las fechas para obtener precios más exactos.
¿Cuánto cuesta el estacionamiento en BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!?
Hay estacionamiento disponible en la propiedad.
¿A qué hora es el check-in en BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!?
Hora de inicio de check-in: 15:00.
¿A qué hora es el check-out en BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!?
El check-out es a las 11:00.
¿Dónde se encuentra BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!?
Este condominio se encuentra en Centro histórico de Key West, a unos pasos de City Zoo Gallery y Duval Street. Playas de los Cayos de la Florida y Barrio de South Beach también se encuentran a 5 minutos.
Opiniones
Opiniones de BOOTLEGGER BAY ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!
9.8
Excepcional
Todas las opiniones que se muestran provienen de experiencias de huéspedes reales. Solo las personas que han reservado un hospedaje con nosotros pueden enviar su opinión. Verificamos las opiniones con base en nuestras pautas y las publicamos todas, ya sean positivas o negativas.Más informaciónSe abrirá en una nueva ventana
10
Limpieza
10
Ubicación
10
Servicio y personal
10
Condiciones de la propiedad
Puntuación de 10, es decir, Excelente. Basada en 9 de 10 opiniones
10 - Excelente
9
Puntuación de 8, es decir, Bueno. Basada en 1 de 10 opiniones
8 - Bueno
1
Puntuación de 6, es decir, Aceptable. Basada en 0 de 10 opiniones
6 - Aceptable
0
Puntuación de 4, es decir, Malo. Basada en 0 de 10 opiniones
4 - Malo
0
Puntuación de 2, es decir, Terrible. Basada en 0 de 10 opiniones
2 - Terrible
0
Opiniones
Opinión verificada
10/10 Excelente
Sarah
25 ago. 2026
Le gustó: Limpieza, servicio y personal, servicios y condiciones de la propiedad
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.
Se hospedó 4 noches en agosto de 2026
Opinión verificada
10/10 Excelente
Kortnie H.
29 may. 2026
Le gustó: Limpieza, check-in, comunicación, ubicación y veracidad del anuncio
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.
Se hospedó 3 noches en abril de 2026
Opinión de un sitio asociado
10/10 Excelente
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.
Opinión de un sitio asociado
10/10 Excelente
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.
Opinión verificada
10/10 Excelente
Amanda S.
20 jul. 2026
Se hospedó 3 noches en junio de 2026
Opinión verificada
10/10 Excelente
THOMAS H.
14 jun. 2026
Le gustó: Limpieza, check-in, comunicación y veracidad del anuncio