Island City House the Oldest Guesthouse in Key West

Although Island City House may be the oldest guesthouse in Key West, it is still grand, beautiful and a wonderful place to stay.  Inside the complex, the garden paths wind you through the property and take you away to a quiet and tranquil place.  The pool is perfect for a quick cool off dip or morning laps, but who really wants to exercise while on vacation?  Located at 411 Wiliam Street, the properties sit between Eaton and Fleming Streets.  Centrally located in Old Town, you won’t be too far from any of the fun.  Across the street, is Eaton Seafood… a personal favorite.  Stop by for lunch, you will be back again and again and again.  Interesting tidbit…the Island City House predates the Casa Marnia Hotel which was built in 1920.

Island City House

I love how the building looks during the Holidays. So festive!

In the Beginning

The home was originally built in 1880 by a wealthy Charleston merchant.  This private residence was in a perfect location when it was the center of town.  By 1908, the owners decided to convert the home into a hotel.  Tourists were expected to flock to Key West once the Over-Sea Railroad was complete.

To ensure there would be enough space, the property was enlarged and a third story was added.  During this remodeling, an interesting piece was added to the top facade of the building.  If you look up, you will see the wooden silhouette of the unique bridge spans of the Over-Sea Railroad.  By 1912, the building was known as the Island City Hotel.

The expansive double porticos across the front and side of the structure were designed to capture fresh ocean breezes and take advantage of the subtropical climate.

Island City House

The Buildings

The property is made up of three buildings.

The Arch House

Built in 1880 as a carriage house, it remains today as the only standing carriage house on the island.  This building has six suites.

Island City House

The Arch of the Carriage House always draws you in.

The Island City House

This is the main building.  This building has 12 suites.

The Cigar House

This is poolside.  It was built to replicate Alfonso Cigar Factory that once was located on the property.  It has six suites.


Island City House today still operates as a guest house. Having stayed in all three of the buildings, my personal favorite is the Arch House.  Located on the Eaton Street side, the front porch is a peaceful place to sit with a cup of morning coffee.  Even if you are not staying at the Island City House, stop by and walk through the Arch of the Carriage House.  It gives you a good sense of how the home felt before it was converted into a hotel.  If you see the resident cat, Burt, stop and say hi.  Island City House offers the best deals if book directly with them.  You can either book directly online or call them.


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