Row Wrapper 2
NIGHTCAP @ Speakeasy Inn Key West!
Capacity
1 Bedroom
1 Bath
Sleeps 2
About
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, 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 limited and not guaranteed, offered on a first come first serve basis at an additional fee of $15 per night. There are also some free as well as metered on street parking spaces on the surrounding streets. Most guests walk or bike ride to all of the nearby attractions once they secure a parking space.
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...
Features
Amenities
- Television
- Air Conditioning
- Hair Dryer
- Parking
- Free Wifi
- Coffee Maker
- Dishes & Utensils
- Microwave
- Refrigerator
- pets not allowed
- Kitchenette
- Ironing Board
- High Speed Internet
- Cable TV
Location
- Speakeasy Inn
Availability
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Map
Reviews
So Cozy
June 2026
Recent Guest, Marriottsville, MD US
Recent Guest, Marriottsville, MD US
Overall
Property condition
Location
Cleanliness
Services from rental manager
Comfy, Cute & Convenient (just bring a sleeping eye mask)
June 2026
Christie D., Longwood, FL US
Christie D., Longwood, FL US
Overall
Property condition
Location
Cleanliness
Services from rental manager
We loved our stay in the Nightcap room at the Speakeasy Inn. There was a little confusion upon checking in, as they never texted us the door code. However, the staff at The Rum Bar downstairs was super helpful, and we got it quickly addressed.
This is a historic building, which comes with it's own quirks. However, the room was very comfortable and welcoming. The king size bed was great. We sleep on an adjustable bed at home, so getting a decent night's sleep on a flat bed when traveling is saying a lot.
The only issue that did impact our sleep was the light. The room gets lots of natural light during the day, which I loved. It was very light and airy. The gauzy curtains fit perfectly for the feel of the room.
However, at night, the lights outside the building are located pretty close to the room. The shades keep prying eyes out, but they are not designed to keep light out. The vast amount of white in the room (which I love during the day,) seems to almost glow at night. The room is never really dark.
All you need to remedy this is a decent sleeping mask, which is why I am not docking their rating because of it. But I wish I had known in advance to bring mine. Here is my heads up to everyone - bring your sleeping mask).
Otherwise, the room is fantastic. They K-cup pods, cream, sweetener, bottled water, to-go coffee cups, coffee mugs, wine glasses, and more. They had beach towels we could use when we hit the water.
The Rum Bar is a great little spot, too. I would definitely stay here again.
Manager's Response
We’re so glad you had a great time with us Christie. It was truly a pleasure having you! We’d be delighted to welcome you back the next time your travels bring you to paradise.
Great location
June 2026
Recent Guest, Altus, OK US
Recent Guest, Altus, OK US
Overall
Property condition
Location
Cleanliness
Services from rental manager
Room was very comfortable and clean. Location is great for walking around the Duval St area.
Manager's Response
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.
Pleasantly Surprised and very Impressed
June 2026
Recent Guest, Mosheim, TN US
Recent Guest, Mosheim, TN US
Overall
Property condition
Location
Cleanliness
Services from rental manager
The property was exactly as described. We were very pleased with the location (within walking distance to everything we wanted to do). The bed was absolutely amazing. Had to be the most comfortable I’ve ever slept in. The owners of this little gem have truly thought of everything a person could need. Having a place to sit outside and watch the people pass by and just enjoy the weather is a huge plus. I will be honest we were a little nervous about the potential noise level being above a bar but were pleasantly surprised that you could not hear any. I would definitely recommend this place and plan on staying there again in the future.
Manager's Response
Thank you for the kind words Jennifer! We’re so happy you enjoyed your stay in paradise and we’d be thrilled to welcome you back for another unforgettable visit.
Beautiful and fun!
May 2026
Cara M., United States
Cara M., United States
Overall
Property condition
Location
Cleanliness
Services from rental manager
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. :)
Manager's Response
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.
Where Mornings Start Suspiciously Well-Rested
April 2026
Recent Guest, United States
Recent Guest, United States
Overall
Property condition
Location
Cleanliness
Services from rental manager
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.
Manager's Response
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.
Girls Weekend!
February 2026
Michelle L., United States
Michelle L., United States
Overall
Property condition
Location
Cleanliness
Services from rental manager
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.
Manager's Response
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.
The property "Speakeasy" was exactly as pictured and very clean. We LOVED sitting out on the balcony and watching the activity on Duvall Street. The Rum Bar downstairs was a great place to go, great atmosphere and people. Location is within walking distance of SO many things! Loved the billowy curtains in the room and the beds were very comfortable.
Manager's Response
Thanks so much for the lovely feedback Nancy! We’re happy to hear you enjoyed the property and would love to host you again in the future.