Coco Plum Inn

Coco Plum Inn is built across two Victorian-era houses on Whitehead Street, one of Old Town’s quieter north-south streets, a single block removed from the shops and bars of Duval. The two buildings share a courtyard and pool, which gives the property a bit more variety in its 14 guest rooms than a single-structure inn typically offers. Some rooms sit at ground level with direct courtyard access, while others are tucked upstairs with a view over the surrounding rooftops and palms, so it is worth asking about room location when booking if a particular setup matters.

Breakfast is prepared on-site each morning and served in a common area, and the inn describes it as professionally prepared rather than a simple continental spread, which lines up with the general trend among Key West’s smaller inns toward a real breakfast rather than pastries alone. The outdoor pool is modest in size but well kept, framed by the kind of dense landscaping that most of Old Town’s historic guesthouses rely on for privacy, since lots here are narrow and buildings sit close to their neighbors.

Rooms come with the practical extras that make a longer stay easier, including in-room coffee makers, mini fridges and microwaves, along with free WiFi throughout the property. On-site massage services are available for guests who want to add some relaxation to the stay without leaving the grounds, and the inn offers a best rate guarantee for those who book directly rather than going through a third party site.

Whitehead Street runs past some of Old Town’s most recognizable landmarks, including the Hemingway House a short walk to the south, and Coco Plum Inn’s location keeps guests close to that stretch without putting them directly on Duval’s busiest block. It is a straightforward, well run bed and breakfast rather than a boutique showpiece, which suits travelers who want comfortable Old Town lodging with genuine hospitality and do not need a long list of resort-style amenities to feel well cared for.

Because the inn is split across two buildings, first-time guests sometimes need a moment to get oriented, and it is worth asking at check-in which structure holds a given room and how to find the shortest path back from the street. The Whitehead Street corridor also runs close to the Key West Lighthouse and the Audubon House, both an easy walk from the property, so guests interested in Old Town’s museums and historic sites have several options within a few minutes on foot. Innkeepers here tend to have deep local knowledge built up over years of running the same property, which can be a genuine resource for anything from dinner reservations to advice on avoiding the busiest hours at nearby attractions.