Entire condo

NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!

Photo gallery for NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!

A covered balcony with wicker chairs, a view of palm trees, and multiple flags. - NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches! (Key West)
A bar area with a wooden bar counter, multiple stools, and a variety of bottles and glasses. - NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches! (Key West)
Two glasses of a red beverage with an orange slice garnish on a table, with playing cards in front. - NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches! (Key West)
A bedroom with a wooden bed, white bedding, a wooden nightstand, a small table, and a dresser. - NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches! (Key West)
A white building with a balcony, palm trees, and flags. - NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches! (Key West)
A short walk from Southernmost Point and Duval Street, NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches! has plenty to offer. Guests can connect to free in-room WiFi.

Reviews

10 out of 10
Exceptional

Entire condo

1 bedroom1 bathroom210 sq ft

Popular amenities

  • Free WiFi
  • Air conditioning
  • Parking available

Add dates for prices

About this property

NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near 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 Nightcap 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 baths with showers.

    SLEEPING ARRANGEMENTS...
    The Nightcap room is located upstairs and offers a king bed with a daybed, a stocked kitchenette, a shower bathroom and a hanging closet.

    OUTDOOR LIVING...
    This unit enjoys outdoor seating off the 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 transportation

  • Parking on site

Food and drink

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Ice maker
  • Microwave
  • Refrigerator

Bedrooms

  • 1 bedroom
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Hair dryer
  • Shower
  • Towels provided

Entertainment

  • TV with cable/satellite channels

Outdoor areas

  • Balcony

Comfort

  • Air conditioning

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city center
  • Near a hospital
  • Near the marina
  • Near the sea

Things to do

  • Basketball nearby
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Jet skiing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkeling 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)
  • Fire extinguisher
  • Deadbolt lock

General

  • Property does not allow children
  • Unit size: 210 square feet

Similar properties

Bar (on property)
Southwinds Motel
Old Town Key West
  • Pool
  • Breakfast included
  • Restaurant
  • Air conditioning
8.6 out of 10, Excellent, 1,381 reviews
The price is CA $174
CA $243 total
includes taxes & fees
Sep 21 - Sep 22
Southwinds Motel
Compare similar properties

Policies

Check-in

Check-in time starts at 3:00 PM

Minimum check-in age: 25

Check-out

Check-out before 11:00 AM

Special check-in instructions

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
Onsite 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 there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
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 neighborhood 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. Ready for a night out? Consider The Key West Theater and Sloppy Joe's Bar. 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. Visit our Key West travel guide
View more Condo rentals in Key West
Map
Key West, FL

What's nearby

  • A street with a pharmacy, a theater, and a yellow building.
    Duval Street
    1 min walk - 0.0 km
  • A beachside resort with palm trees, a large white building, and a checkered pattern on the sand.
    South Beach
    3 min walk - 0.3 km
  • A butterfly on a plant with green leaves and yellow flowers.
    Key West Butterfly and Nature Conservatory
    3 min walk - 0.3 km
  • A vintage typewriter on a wooden table with a notebook and pen beside it.
    Ernest Hemingway Home and Museum
    4 min walk - 0.4 km
  • A colorful monument with text indicating it is the Southernmost Point of the Continental U.S.A. in Key West, Florida.
    Southernmost Point
    5 min walk - 0.4 km

Getting around

  • Key West Intl. Airport (EYW)
    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 NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches! pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!?

As of Sept 20, 2026, prices found for a 1-night stay for 2 adults at NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches! on Sept 27, 2026 start from CA $164, 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?

Onsite parking is available at the property.

What time is check-in at NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!?

Check-in begins at 3:00 PM.

What time is check-out at NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!?

Check-out is at 11:00 AM.

Where is NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches! located?

Located in Old Town Key West, this condo building is steps from City Zoo Gallery and Duval Street. Florida Keys Beaches and South Beach are also within 5 minutes.

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near 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.
More informationOpens in a new window
Rating 10 - Excellent. 12 out of 13 reviews
Rating 8 - Good. 1 out of 13 reviews
Rating 6 - Okay. 0 out of 13 reviews
Rating 4 - Poor. 0 out of 13 reviews
Rating 2 - Terrible. 0 out of 13 reviews

10

Cleanliness

10

Location

10

Staff & service

10

Property conditions & facilities

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Our recent stay at the Speakeasy Inn above the Rum Bar in Key West was absolutely wonderful. The atmosphere was amazing from the moment we arrived—charming, lively, and full of that classic Key West character. The staff was incredibly friendly and welcoming, which made the experience even better. The room was very clean, comfortable, and thoughtfully stocked with everything we needed during our stay. It had such a cute, cozy feel that really added to the charm of the place. One of our favorite parts was the adorable balcony. It was the perfect spot to relax, enjoy some quality time, and do a little people-watching while soaking in the energy of the area. Overall, it was a fantastic stay and we would absolutely come back again! 🌴🍹
Stayed 2 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful stay, location was great!
Stayed 3 nights in Apr 2026
From a partner site

8/10 Good

Great location

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: Room was very comfortable and clean. Location is great for walking around the Duval St area.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved our stay! Great location and wonderful room. The bed was super comfortable and the balcony was a great spot for people-watching with a cup of coffee. Since the room is above a bar, there’s music all day and into the night - it didn’t really bother us, but something to keep in mind. Overall, a great stay and we’d definitely stay here again!
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The room was just as described. We were a little nervous at first about the possible noise level from the bar below but to our surprise you could barely hear anything. The bed has to be the most comfortable I have ever slept on. The room was very clean and in the perfect location (walking distance) to everything we wanted to see. I would definitely stay here again if I’m ever back in Key West.
Stayed 3 nights in Jun 2026
From a partner site

10/10 Excellent

Beautiful and fun!

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: The room was perfect! The balcony looked out onto Duval, and was great for early morning coffee or a late night drink. The bar downstairs was fun and the bartender was always great! And can't forget Captain, he was my favorite. :)
From a partner site

10/10 Excellent

Girls Weekend!

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: Easy to deal with company and room access. Nice clean room, great location, friendly staff and A/C was always working which is a big plus in the Keys.
From a partner site

10/10 Excellent

Where Mornings Start Suspiciously Well-Rested

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: I didn’t just stay here—I temporarily entered a higher plane of existence, one duvet at a time. The bed was so outrageously comfortable that every morning I woke up in a mild panic, convinced I had somehow slept through an entire day... only to discover it was still early. Turns out, this is what well-rested humans feel like—who knew?For the first time in recent memory, I woke up without that familiar “I need another eight hours” exhaustion. Instead, I felt suspiciously refreshed, like I’d been rebooted overnight by a team of highly skilled sleep technicians.Beyond my newfound relationship with rest, the place itself delivered on all fronts. The location was perfect—close enough to everything, yet peaceful enough to pretend you’ve got your life together. And the balcony? Let’s just say it made me briefly consider becoming the kind of person who drinks coffee slowly while gazing thoughtfully into the distance.All in all, it’s everything you want in a place to stay: comfortable, beautiful, and dangerously good at making you forget your responsibilities. If you need me, I’ll be trying (and failing) to recreate that bed experience at home.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Mark was FABULOUS! The room was absolutely ADORABLE and a very nice size for 2 or 3 or three people. The bar, beneath which was the room, their staff were extremely helpful and gracious as well. Jewels, Frank & Sparkles were also FABULOUS!!
Stayed 4 nights in Jun 2026