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 House
Originally, 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 Victorian antiques, lace curtains and hardwood floors.

The Arch House: Built as a carriage house to the Main house in the 1880’s, it remains the only standing carriage house on the island. This two story house, trimmed with gingerbread, allows the island trade winds to pass through its arch and into the tropical gardens within. This house currently offers 6 suites furnished in a casual island style of bright colors against cool white wicker, Bahama ceiling fans, and hardwood floors.