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.

Built in 1894, the delightful Inn on Fleming was once the residence of Board of Education chair Glynn Archer until it was transformed into what is now a serendipitous tropical refuge, boasting 9 unique rooms and suites and tucked into a peaceful residential street. You are only two blocks from the Historic Seaport and a short stroll to 5 star restaurants, bars, shopping and the endless allure of famous Duval Street. The magic begins as you step onto our cozy wraparound porch with comfortable and plentiful seating. Retreat to our tropical garden to savor a cup of coffee in the morning. Sip on a crafted cocktail in the afternoon and take a dip in our lush tropical pool featuring a soothing and relaxing waterfall. All of our rooms feature Serta PerfectSleeper Prestige Suite 11 Mattresses, fine linens, flat screen TV, coffeemaker, a mini-fridge, countertop ice machine, as well as tropical garden views. Bikes are available to rent for your outdoor adventures. The Whitehead Room is located on the 2nd floor and offers a queen bed. Enjoy your privacy in this location that is accessible from the back deck with lounge furnishings. Dade County pine walls and an ensuite bathroom with a tub/shower combination complete the cozy space. This room connects to the Truman Room. We do not have our own parking but there is plenty of free on-street parking. GUESTS MUST BE 25 YEARS OF AGE OR OLDER.