The Island City House Hotel is the oldest operating guesthouse on Key West. It is comprised of three buildings: the Carriage House, the Island City House and the Cigar House. Each building lends its own unique history and style to the property. The Island City HouseOriginally, built as a private home for a wealthy Charleston merchant family in the 1880’s, this grand three-story Victorian mansion was then converted into the Island City House Hotel by its owners, in anticipation of the railroad’s arrival in 1912. Today after a faithful restoration, this house offers 12 parlor suites, each individually furnished with ...