FENWAY HOTEL, AUTOGRAPH COLLECTION, Dunedin

Fenway Hotel, Autograph Collection - A historic 1924 jazz-era hotel with rooftop bar, steakhouse, and waterfront views

Located on Edgewater Drive facing Caladesi and Honeymoon Islands, this 2-star Dunedin hotel occupies a historic 1924 building that once housed the county's first radio station. The Fenway Hotel, Autograph Collection features 83 rooms, including 18 suites, with vintage-inspired design and premium bedding. The HEW Parlor & Chophouse serves steakhouse fare and specialties like Cock-a-leekie soup and wild boar chops, while Room 27 offers a 1920s speakeasy experience. The Hi-Fi Roof Bar provides sunset views and locally-inspired cocktails. Amenities include a resort-style pool, fitness center, and bicycle rentals for exploring the 40-mile Pinellas Trail. The Autograph Collection property's historic lawn hosts outdoor activities including badminton, bocce, and croquet. The hotel sits directly across from the intracoastal waterway, with Caladesi Island State Park just 2 miles away.

Pros

Historic 1924 building with preserved jazz-age character and radio station heritage

Waterfront location with views of Caladesi and Honeymoon Islands

Extensive whisky and Scotch collection reflecting local Scottish heritage

Front lawn hosts regular outdoor events and activities

Cons

21.5 miles from Tampa International Airport

Limited on-site dining options after 10 PM