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History | Key West Florida Hotel

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 Arch House
Built as a carriage house to the Main house in 1880, 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.

The Island City House
Originally, built as a private home for a wealthy Charleston merchant family in 1880, 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.

After a faithful restoration, this house offers 12 parlor suites, each individually furnished with Victorian antiques, lace curtains and hardwood floors.

The Cigar House
This red cypress wood house was built to replicate the Alfonso Cigar Factory that once occupied this site approximately one hundred years earlier. Overlooking the pool, this house is nestled quietly in the rear garden and shaded by swaying palms.

The house offers 6 of our most spacious parlor suites, individually furnished in elegant tropical plantation style, rattan furnishings, Bahama ceiling fans, French doors, and hardwood floors.