Weatherstation Inn

Weatherstation Inn takes its name and its building from a genuinely unusual piece of Key West history: the structure on Front Street dates to 1911 and originally served as a weather observation station tied to the historic Navy installation that once occupied much of what is now the Truman Annex area. That naval history is still visible in the surrounding gated community, a quieter, more residential pocket of Old Town than the streets around Duval.

The inn operates as an adults-only bed and breakfast, and the gated setting gives it a level of privacy and calm that is harder to find on the busier commercial blocks closer to the center of town. Guests reach the property through the same gated entry that serves the surrounding Truman Annex neighborhood, adding a sense of separation from the rest of Old Town’s foot traffic.

The property has recently become part of Ocean Breeze Inns, a small collection of independent boutique inns spread across a handful of Florida coastal towns, while the day-to-day operations and existing staff at the Key West property have reportedly stayed in place through that transition. Because this affiliation is relatively new and the resulting ownership structure was not fully documented in public sources at the time of research, travelers who place particular importance on single-owner, Key West-based management should confirm current ownership details directly with the property before booking.

For guests who want a historically distinctive building, a genuinely quiet gated setting, and proximity to both the Truman Annex and the rest of Old Town, Weatherstation Inn remains a notable choice, with the caveat that its ownership structure has shifted in the recent past.

The Truman Annex neighborhood surrounding the inn developed from the decommissioned naval base that once occupied much of this part of the island, and it retains a distinctly different character from the commercial bustle of Duval Street, with quiet streets, restored military-era buildings and direct access to Fort Zachary Taylor State Park nearby. Guests who value that kind of historical and residential setting over a Duval Street address tend to be the ones who seek this property out specifically. Prospective guests should reach out directly to confirm current ownership and management details given the property’s recent change in affiliation. The building’s original function as a weather station is a genuinely unusual footnote in Key West’s naval history, and travelers with an interest in that period of the island’s past will find the inn itself, and the surrounding Truman Annex grounds, worth a slower look beyond just an overnight stay.