Westwinds Inn

Westwinds Inn sits on Eaton Street in the Historic Seaport District of Old Town, in a Victorian-style building dating to roughly 1900. With 26 rooms, it is one of the larger properties in this category, spread across a couple of connected structures rather than a single small guesthouse, though the general layout, rooms arranged around courtyards and pools, keeps it feeling consistent with its smaller neighbors rather than like a conventional hotel.

Two pools give the property enough capacity to handle a full house without either pool feeling overcrowded, and a complimentary breakfast is served poolside each morning between 8:00 and 10:00. A happy hour runs on weekday afternoons, and bike rentals along with on-site massage services are available for guests who want to build a full day of activity, or relaxation, into a stay without leaving the grounds.

The Historic Seaport location keeps guests close to the Key West Bight, with its charter boat docks, seafood restaurants and Mallory Square sunset gathering, while Duval Street is a short walk in the other direction. Westwinds has picked up TripAdvisor Travelers’ Choice recognition and also hosts small weddings and group events on-site, taking advantage of its larger footprint compared to some of the smaller boutique inns nearby.

For groups or travelers who want more room inventory and amenity redundancy, two pools instead of one, while still staying at an independently branded, historically detailed property rather than a large chain hotel, Westwinds Inn offers a scale that few of Old Town’s smaller guesthouses can match.

The Historic Seaport itself has grown into one of Key West’s more popular evening destinations in recent years, with waterfront restaurants and bars drawing a steady crowd around sunset, and staying at Westwinds puts guests within an easy walk of that whole stretch. Because the property spans 26 rooms across more than one building, it is worth requesting a specific pool or courtyard area when booking if a particular setting matters, since not every room looks out on the same view. Repeat guests often mention the poolside breakfast as a highlight, since eating outdoors in the morning before the day heats up is one of the small pleasures that a larger, indoor-lobby hotel cannot easily replicate. The inn’s willingness to host weddings and group functions also makes it a practical option for a family gathering or reunion that needs more rooms under one roof than a six or eight room guesthouse could accommodate.