NIGHT WATCH ~ 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 Night Watch 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! 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 Night Watch room is located downstairs and offers a king bed and 1 person sofa sleeper, a stocked kitchenette, a shower bathroom and a hanging closet for your convenience.
OUTDOOR LIVING... Take in the island air and sip on your frosted cocktail just outside of your room, with semi-private seating. 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...
Our prices include all fees. No hidden fees.
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AFTER HOURS ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!
Uptown - Upper Duval
AFTER HOURS ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
About the area
Key West
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. Jet skiing and scuba diving offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and cycling nearby.
Key West, FL
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, FL (EYW-Key West Intl.) - 12 min drive
Restaurants
Circle K - 1 min walk
Cuban Coffee Queen (Duval) - 1 min walk
Southernmost Point Bar in the USA - 4 min walk
Old Town Tavern - 4 min walk
Banana Cafe - 1 min walk
Frequently asked questions
Is NIGHT WATCH ~ 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 NIGHT WATCH ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!?
As of 25 Sept 2026, prices found for a 1-night stay for 2 adults at NIGHT WATCH ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches! on 7 Sept 2027 start from £228, including 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 NIGHT WATCH ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!?
On-site parking is available at the property.
What time is check-in at NIGHT WATCH ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!?
Check-in begins at 3:00 PM.
What time is check-out at NIGHT WATCH ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!?
Checkout is at 11:00 AM.
Where is NIGHT WATCH ~ 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 Ernest Hemingway Home and Museum are also within 10 minutes.
Reviews
9.4
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Loved the Speakeasy room. Perfect location and everything we needed. Would recommend and would definitely stay here again.
Stayed 2 nights in Jul 2026
Response from VrboOwner on 1 Sept 2026
We’re grateful for your glowing review! It was such a pleasure to host you, and we’re already looking forward to your return to the island.
From a partner site
10/10 Excellent
Paul B.
14 May 2026
Had a great time. Love the run bar
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:
Everything was wonderful
Response from VrboOwner on 19 May 2026
We’re grateful for your glowing review Paul! It was such a pleasure to host you, and we’re already looking forward to your return to the island.
Verified review
6/10 Okay
Scarlett S.
24 Aug 2026
Liked: Cleanliness, location, listing accuracy
Disliked: Check-in, communication
Location was great, place was clean, bar and bartenders were excellent. Check-in was awful and what it made it worse was to find out that this has happened many times before. The mgmt company is aware that texts are not received by people with Android yet insists they can somehow fix it if you call them. No they can't. I shouldn't have to track down and call multiple people to get an email with my access code!! I found out from workers that many have similar experiences and complained about it. So, the owner knows as well. Fix it!
Stayed 2 nights in Jun 2026
Response from VrboOwner on 8 Sept 2026
Thank you for your feedback. We’re glad you enjoyed the location, cleanliness of the property, and our bar and bartenders. We’re sorry you had difficulty receiving your entry code. Because we are aware that our texts can sometimes be filtered into spam or not delivered, we specifically warn guests about this in three separate communications: the initial confirmation email, a reminder four days before arrival, and again the day before arrival. Each communication clearly states: PLEASE BE AWARE: Our texts often end up in your text spam folder, so please add the innkeeper’s number, 305-407-0779, to your contacts to ensure you receive your entry code. We certainly understand that check-in should be straightforward, which is why we provide these instructions well in advance. We appreciate your feedback and will continue working to make the process as seamless as possible.
Absolutely wonderful place, the Rum Bar was amazing Frank was so nice and friendly. The Bed is so comfortable and it’s right off Duval Street. Absolutely loved it here!!
Stayed 2 nights in Jun 2026
Response from VrboOwner on 30 Jun 2026
Thank you for the kind words Amanda! We’re so happy you enjoyed your stay in paradise and we’d be thrilled to welcome you back for another unforgettable visit.
Verified review
10/10 Excellent
Brandon R.
12 May 2026
Stayed 3 nights in Apr 2026
Response from VrboOwner on 29 May 2026
Thank you for the awesome rating Brandon! We are so happy you loved your stay with us and hope you'll return!
Verified review
10/10 Excellent
Laurie L.
10 Apr 2026
Stayed 1 night in Mar 2026
Response from VrboOwner on 27 Apr 2026
Thank you for the excellent rating Laurie! We hope you'll come back soon as our treasured guest!