Dwell Key West

Dwell Key West Experience historic Key West in our boutique accommodations where you can feel immersed in the quintessential charm of Key West.

Step into your own little slice of Key West charm ✨The Quiet Pour room at the Speakeasy Inn & Rum Bar is where comfort m...
04/05/2026

Step into your own little slice of Key West charm ✨

The Quiet Pour room at the Speakeasy Inn & Rum Bar is where comfort meets island indulgence. Tucked upstairs, this beautifully restored space features a plush king bed, a stocked kitchenette, and a spa-like bathroom complete with a soaking tub perfect for unwinding after a day on Duval Street.

Sip something frosty on the wraparound porch just outside your door and take in the lively energy below!

An impressive rum bar awaits downstairs, offering tastings from around the world, from beloved favorites to rare vintage pours.

Whether you’re here to relax, explore, or savor every sip, the Quiet Pour room is your perfect home base! Come see for yourself.

https://www.dwellkeywest.com/key-west-vacation-rentals/quiet-pour-speakeasy-inn-key-west

✨ GRAND RE-OPENING ✨Step into a story where rum runners, hidden cellars, and Prohibition-era secrets come alive. The Spe...
04/03/2026

✨ GRAND RE-OPENING ✨

Step into a story where rum runners, hidden cellars, and Prohibition-era secrets come alive.

The Speakeasy Inn & Rum Bar brings historic charm, tropical elegance, and one of the most celebrated rum selections in Key West right to the heart of Duval Street.

Sip, stay, and soak in the magic from our wraparound porch, just steps from the beach and the Southernmost Point.

🍹 Rum tastings
🌴 Adult-only escape (21+)
🗝️ Rich history restored to perfection

Your after-hours adventure starts here! Book your stay and check out the beautiful updates!

https://www.dwellkeywest.com/key-west-vacation-rentals/after-hours-speakeasy-inn-key-west

Step into a story you’ll never forget… 🍹✨Hidden in the heart of Key West, our Night Watch Room at the Speakeasy Inn invi...
03/23/2026

Step into a story you’ll never forget… 🍹✨

Hidden in the heart of Key West, our Night Watch Room at the Speakeasy Inn invites you to live a little history. Once home to a daring rum-runner with a secret cellar, this charming 19th-century hideaway is filled with tales of Prohibition-era adventure, treasure hunts, and moonlit smuggling trips to Cuba.

Stay just steps from Duval Street, where art, food, and island nightlife come alive, and unwind with a world-class rum selection right downstairs at our celebrated Rum Bar. Sip, savor, and soak in the magic from your private outdoor space or our iconic wraparound porch.

🌴 Adult-only escape (21+)
🥃 Daily rum tastings
🏝️ Walk to the beach & Southernmost Point
🛏️ Cozy king suite with modern comforts

Ready to experience Key West like never before? Your unforgettable getaway starts here: https://www.dwellkeywest.com/key-west-vacation-rentals/night-watch-speakeasy-inn-key-west

Quiet Pour 🍹Located on the second floor of The Speakeasy Inn offering a king bed, a stocked kitchenette, and a bathroom...
03/22/2026

Quiet Pour 🍹

Located on the second floor of The Speakeasy Inn offering a king bed, a stocked kitchenette, and a bathroom that includes a shower and soaking tub for your enjoyment.

Take in the island air and sip on your frosted cocktail just outside of your room, or head upstairs to our wraparound porch overlooking Duval Street, a favorite people-watching spot! It has been restored to perfection for the pleasure of our guests.

https://www.dwellkeywest.com/key-west-vacation-rentals/quiet-pour-speakeasy-inn-key-west

Smuggler's Cove is located on the first floor of the Speakeasy Inn, nestled in Key West magic. ✨This unique, conch-style...
03/22/2026

Smuggler's Cove is located on the first floor of the Speakeasy Inn, nestled in 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!

Come join the adventure and experience the island like a local!

https://www.dwellkeywest.com/key-west-vacation-rentals/smugglers-cove-speakeasy-inn-key-west

Turn up the heat at 🔥🍹Introducing our newest cocktail at the Rum Bar inside The Speakeasy Inn…🌶️ Captain’s Cat Scratch ...
03/21/2026

Turn up the heat at 🔥🍹

Introducing our newest cocktail at the Rum Bar inside The Speakeasy Inn…

🌶️ Captain’s Cat Scratch Fever 🌶️

Named after iur very own Captain 🐾 the true boss of the bar and a local legend around the Inn.

This bold, spicy twist on a margarita is made for tequila lovers who like a little kick:

✨ Tanteo jalapeño tequila
✨ Triple sec
✨ Fresh lime juice
✨ Cane syrup
✨ Finished with a hot honey & Tajín rim

It’s sweet, spicy, and just the right amount of wild — just like the Captain himself 😏

Staying with us or just passing through, everyone’s welcome!
Stop in, meet the Captain, and sip something unforgettable in Key West!

🍀 Celebrate St. Patrick’s Day in style at The Rum Bar! 🍀If you’re staying with us at The Speakeasy Inn (or just nearby),...
03/17/2026

🍀 Celebrate St. Patrick’s Day in style at The Rum Bar! 🍀

If you’re staying with us at The Speakeasy Inn (or just nearby), swing by and sip on festive favorites like Tully Green Tea’s, Lucky Charm Shots, and Leprechaun Punch!

Good drinks, island vibes, and a little Irish luck, what more could you need? 🍀

Stop in, raise a glass, and eat, drink & be Irish! 🍻

The Hideaway room within the Speakeasy Inn is nestled in true Key West magic! ✨This unique, conch-style, adult-only retr...
03/13/2026

The Hideaway 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 Hideaway room is located upstairs and offers a king bed, a stocked kitchenette, a shower bathroom, and a clothing wall hanging system for your convenience.

Take in the island air and sip on your frosted cocktail just outside of your room, with cushioned seating for your enjoyment. 🍹

Come join the adventure! Visit our website for full details and availability.

Be honest…Are you more:A) Rooftop cocktailsB) Hidden historic hideawayC) Adults-only island retreatD) All of the aboveIf...
02/23/2026

Be honest…

Are you more:
A) Rooftop cocktails
B) Hidden historic hideaway
C) Adults-only island retreat
D) All of the above

If you chose D, we should talk. 🍹

DM us for the link to book and enjoy the rich 19th century lore of treasure hunts, romantic rum-running adventures, daring bootleggers, and notorious moonshiners and racketeers.

It’s go time 🙌🏼 The Speakeasy Inn is officially LIVE and ready for bookings! Step into a one-of-a-kind, adults-only conc...
02/09/2026

It’s go time 🙌🏼 The Speakeasy Inn is officially LIVE and ready for bookings!

Step into a one-of-a-kind, adults-only conch-style retreat steeped in prohibition-era lore. Once home to Raul Vasquez, a legendary rum runner who smuggled spirits between Key West and Cuba and hid them away in his secret cellar (one of the only basements in Key West).

📍 Located on iconic Duval Street
🌴 3 blocks from the beach, Southernmost Point & Mallory Square
🥃 On-site Rum Bar featuring rums from around the world

The Speakeasy Inn is where history, nightlife, and island charm collide. Come see for yourself! Visit our website for full details and photos, or DM us for the link to book.

02/06/2026

A new chapter begins on Duval Street ✨

Dwell Key West is excited to announce that we’ll be managing the Speakeasy Inn on Duval. Going live February 9th!

Follow for updates, photos, and booking details. You won’t want to miss this!

Address

Key West, FL
33040, 33041, 33045

Website

Alerts

Be the first to know and let us send you an email when Dwell Key West posts news and promotions. Your email address will not be used for any other purpose, and you can unsubscribe at any time.

Shortcuts

Share

Category