Douglas House Hotel
Douglas House is a guesthouse on Amelia Street in Old Town Key West, twenty-one rooms across two floors arranged around a swimming pool set in tropical gardens. It is a block off Duval, which is the right distance: close enough to walk to everything, far enough that the street noise stays on the street.
Accommodations range from Queen Rooms up through Suites with one or two queen beds and King Suites with sitting areas, and some units have kitchenettes or full kitchens if you would rather make your own coffee than find it. Wi-Fi is free and genuinely fast. Complimentary tea and coffee are out all day, and there is a wine and spirits list if you want something stronger brought to the pool.
The house has a stated personality, which is worth knowing before you book. This is not a party property. They do not take spring break bookings or bachelor and bachelorette groups, and they discourage parties of more than six gathering in the common areas. If you are looking for somewhere to read a book in the shade and hear birds instead of a cover band, that is the point.
Check in runs from 4:00 to 8:00 pm and check out is at 11:00 am, so call ahead if you are arriving late. Duval Street, the Hemingway Home, the Lighthouse and the whole of Old Town are walkable from the front gate, and the same owners run The Paradise Inn and Cabana Inn nearby if your dates are full here.