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.
A bedroom with a wooden bed, white bedding, a wooden nightstand, a small table, and a dresser.
A white building with a balcony, palm trees, and flags.
Two glasses of a red beverage with an orange slice garnish on a table, with playing cards in front.
A bar area with a wooden bar counter, multiple stools, and a variety of bottles and glasses.

Reviews

10 out of 10
Exceptional

Highlights

  • Top-rated comfy beds
    Guests liked the comfy beds here.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Near Duval Street
1 bedroom1 bathroomSleeps 3

Popular amenities

  • Balcony
  • Air-conditioning
  • Refrigerator
  • Onsite parking available
  • Internet
  • Non-smoking

Explore the area

View in a map
Key West, FL
  • Place, Duval Street
    ‪1 min walk‬
  • Place, South Beach
    ‪3 min walk‬
  • Place, Southernmost Point
    ‪5 min walk‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪9 min drive‬

Rooms & beds

1 bedroom (sleeps 3)

Bedroom 1

1 King Bed

Other Space 1

1 Single Bed

1 bathroom

Bathroom 1

Toilet · Shower only

Spaces

Balcony

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...
Our prices include all fees. No hidden fees.

Add dates for prices

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House Rules

Check in after 3:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Adults only
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property # 5092058vb
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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

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. 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.
Map
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 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 23 Sept 2026, prices found for a 1-night stay for 2 adults at NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches! on 7 Sept 2027 start from ÂŁ214, 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 NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!?

On-site 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!?

Checkout 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 away from City Zoo Gallery and Duval Street. Florida Keys Beaches and Ernest Hemingway Home and Museum are also within 10 minutes.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 13 out of 14 reviews
Rating 8 - Good. 1 out of 14 reviews
Rating 6 - Okay. 0 out of 14 reviews
Rating 4 - Poor. 0 out of 14 reviews
Rating 2 - Terrible. 0 out of 14 reviews

10/10

Cleanliness

10/10

Staff & service

10/10

Amenities

10/10

Property conditions & facilities

9.8/10

Check-in

9.8/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful stay, location was great!
Stayed 3 nights in Apr 2026
Response from VrboOwner on 8 Jul 2026
We’re so glad you had a great time with us Taffy. It was truly a pleasure having you! We’d be delighted to welcome you back the next time your travels bring you to paradise.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Clean bright fresh comfortable room, nice property, fun bar.
Stayed 5 nights in Jun 2026
Response from VrboOwner on 28 Jul 2026
We’re so glad you had a great time with us. It was truly a pleasure having you! We’d be delighted to welcome you back the next time your travels bring you to paradise.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Comfortable beds and wonderful atmosphere
Stayed 2 nights in Jun 2026
Response from VrboOwner on 17 Jul 2026
Thanks so much for the lovely feedback! We’re happy to hear you enjoyed the property and would love to host you again in the future.
From a partner site

10/10 Excellent

Best spot on Duval!

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: We came to Key West for a long weekend and stayed at the speakeasy inn in the nightcap room. It was awesome! Plenty of room, comfortable bed and everything you need. Parking was so easy and well priced! The rum bar is so great too, friendly and attentive bartenders, cozy atmosphere that just makes you feel right at home and Captain the cat is a highlight. Can’t wait to stay again!
Response from VrboOwner on 18 Sept 2026
What a joy to read your review - thank you so much! We’re so glad you loved your time in paradise and can’t wait to have you back on the island soon.
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.
Response from VrboOwner on 24 Jun 2026
Your kind words mean the world to us Rusty! Hosting you was an honor, and we can’t wait for the chance to welcome you back to our little slice of paradise.
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
Response from VrboOwner on 12 Jun 2026
We’re so glad you had a great time with us Deb. It was truly a pleasure having you! We’d be delighted to welcome you back the next time your travels bring you to paradise.
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
Response from VrboOwner on 25 Jun 2026
Your kind words mean the world to us Jennifer! Hosting you was an honor, and we can’t wait for the chance to welcome you back to our little slice of paradise.
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. :)
Response from VrboOwner on 24 Jun 2026
We’re grateful for your glowing review Cara! 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

Even Better than I Could Have Imagined

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: Such an amazing time at The Speakeasy. The location was absolutely perfect. Walking distance to everything. The room was exactly as it's described. It was clean, well stocked, everything worked great. Check-in was quick and easy. All the staff was very nice. The Rumbar right downstairs was the cherry on top. Great drinks, great bartenders, great conversation. Everybody I talk to is jealous that I was staying in the room right upstairs. The wraparound balcony was excellent. I can't recommend this place enough. I will definitely be staying here again. Also, say hi to Captain for me!
Response from VrboOwner on 4 Aug 2026
Thanks so much for the lovely feedback! We’re happy to hear you enjoyed the property and would love to host you again in the future.
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.
Response from VrboOwner on 10 Mar 2026
We’re grateful for your glowing review Michelle! It was such a pleasure to host you, and we’re already looking forward to your return to the island.
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
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.
Response from VrboOwner on 28 Apr 2026
We’re grateful for your glowing review Maureen! 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

Nightcap on Duval

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: Wow, what a great find!! This is a wonderful location, a bit on the east side of Duval which was nice not being right in the heart of things. We did come down in September so it was a bit quieter which we enjoyed. We loved being above the Speakeasy. The bartenders were fantastic. I'd highly recommend this location. The communication was spot on. We did reserve a parking spot and very glad that we did. The parking lot was about a half block walk and we left our car there and just walked everywhere. The property was very clean and very well maintained.
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
Response from VrboOwner on 30 Jun 2026
Thank you for the kind words Christine! We’re so happy you enjoyed your stay in paradise and we’d be thrilled to welcome you back for another unforgettable visit.

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