Dwell Key West

08/22/2026

Stay somewhere with a story…

Speakeasy Inn • Key West, FL
Adults Only • 21+

This unique conch-style retreat is filled with stories of Prohibition, rum running, and the characters who made Old Town what it is today. Art galleries, unforgettable restaurants, lively bars and all the colorful energy of Key West are right outside your door.

Come soak up the sun and experience the history of Key West in our boutique accommodations.

DM us for the link to book.

08/13/2026

Dwell Key West is hiring! 😎

Join our team as an Innkeeper where you can contribute to creating a positive living experience for our guests while developing your career in property management!

Job Type: Full-time
Work Location: In person

Scroll through for details and email your resume to [email protected].

07/04/2026

Happy Independence Day from Dwell Key West! 🇺🇸

06/05/2026

Cornish Suite is located on the 3rd floor of the Inn on Fleming and offers two bedrooms, suitable for up to 4 guests.

The first room offers a plush king bed, a sitting area and mini-fridge. The second bedroom features a double bed and provides access to the full, private bathroom with shower. The sloping ceiling over the bed makes for a cozy nook in your nighttime retreat. You will find an outdoor deck with lounge furniture just outside of the room.

Visit our website using the link below to book your stay at the Inn on Fleming!

THE CORNISH SUITE ~ Adults Only, 3rd Floor, 2 Bedroom Suite at Inn on Fleming Guesthouse w/ Shared Pool!

06/04/2026

Bootlegger Bay at Speakeasy Inn Key West 🍹

Steeped in the rich 19th century lore of treasure hunts, romantic rum-running adventures, daring bootleggers, and notorious moonshiners and racketeers, the Bootlegger Bay 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.

Come join the island adventure! Visit our website for full details on this incredible property, or DM us for the link to book.

05/25/2026

This , we remember and honor the brave heroes who made our freedom possible. 🇺🇸

05/24/2026

Royal Palm Studio has availability in June! 💙

Immerse yourself in this exquisite, adult only, tropical compound of Travelers Palm offering beautiful garden views to refresh your soul.

This inviting studio is a traveler's delight that lures you in offering updated tropical furnishings and creature comfort essentials.

Visit the link below for full details and book your summer vacation with Dwell Key West!

ROYAL PALM STUDIO ~ Adult Only, Charming Studio with Kitchenette in Travelers Palm Inn, Community Pool, Parking and Convenience to Downtown!

05/23/2026

What are your plans next month?

Come delight in old world allure at the Scarlet Mango Inn! This exclusive king suite is flooded with Key West sunshine from large windows and a private door leading out to the upper porch. The light and airy decor of the living room instantly puts you in relaxed vacation mode.

Visit our website using the link below and come get on island time! ☀️

Stay at Scarlet Mango Inn in Key West and indulge in an elegant second-floor king suite with private porch access, spacious living area, and Bahamian-style charm. Enjoy lush gardens, a heated pool, and easy access to Duval Street and beaches.

05/13/2026

Speakeasy Inn 🍹

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!

Right on Duval Street, nestled in the heart of Old Town, you are only 3 blocks from the beach, the Southernmost Point, Mallory Square, and the world famous Sunset Celebration.

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

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