Island City House

Island City House Hotel is often described locally as the oldest continuously operating guest house in Key West, with a history on William Street dating back to 1912. Rather than one building, the property is actually three separate historic structures: the Island City House itself, the Arch House, and the Cigar House, each with a slightly different architectural character reflecting different periods of Key West’s building history. Guests can request a specific building when booking, and the differences are noticeable enough that repeat visitors often have a preference.

The three buildings share a single courtyard, centered on an in-ground pool surrounded by dense tropical landscaping, and suites throughout the property tend to include separate living areas and full kitchens rather than a simple hotel room layout. That configuration makes Island City House a good fit for longer stays, since guests can prepare their own meals rather than eating out for every breakfast, lunch and dinner.

On-site massage services are available through the property’s Essera Spa, and bike rentals are offered for guests who want to explore Old Town without relying on a car or the town’s limited parking. William Street sits within easy walking distance of both Duval Street and Mallory Square, so the location works well as a base for exploring on foot.

Because the buildings are historic rather than purpose-built as a hotel, room shapes and layouts vary more than at a standard property, and the inn’s staff are generally well versed in explaining those differences to help match guests with the right suite. For travelers who want to stay somewhere with a documented, more than century-long history of continuous operation, rather than a property that has simply occupied an old building for a few decades, Island City House is one of the more historically grounded choices in Key West.

The Cigar House in particular draws on Key West’s cigar manufacturing history, a major industry on the island through the late nineteenth and early twentieth centuries before it largely relocated to Tampa, and its name reflects that earlier use of the building. Guests staying in suites with full kitchens often use the property as a base for a week or more rather than a quick weekend trip, taking advantage of the ability to cook breakfast or a light dinner without needing to eat out for every meal. William Street’s location, tucked between Duval and the quieter residential blocks toward the harbor, keeps the inn walkable to both the town’s main attractions and its calmer corners.