Experience historic Key West in our boutique accommodations where you can feel immersed in the quintessential charm of Key West. We believe the best way to travel is to feel like a local, which is why we offer a curated collection of lodging properties on the island. Take advantage of our concierge services to make the most of your vacation here. The Dwell Key West family is a passionate team of professionals with extensive property management background here to provide the most seamless and enjoyable Key West experience for travelers. With a successful performance history within the Key West property management industry, our team is here to ensure a professional and dependable service for the maintenance and preservation of all of our acquired Key West rentals.

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. 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. You are right on Duval Street, renowned for its proliferation of whimsical art galleries, stellar restaurants and relaxing bars. Tucked in the heart of Old Town, you are only 3 blocks from the beach and the Southernmost Point. 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. Amenities in the room include a flat screen TV, individually operated AC, coffee maker, refrigerator, microwave, and a private bath with shower. The Bootlegger Bay room is located downstairs and offers a queen bed. Take in the island air and sip on your frosted cocktail just outside of your room, with cushioned seating for your enjoyment. Upstairs features our wraparound porch overlooking Duval Street, a favorite people-watching spot! It has been restored to perfection for the pleasure of our guests. Parking is limited and not guaranteed, offered on a first come first serve basis at an additional fee. There are also some free as well as metered on street parking spaces on the surrounding streets. 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.