Fenway Hotel, Autograph Collection, Dunedin

Fenway Hotel, Autograph Collection - A boutique hotel with historic charm, rooftop bar, and proximity to top beaches

Fenway Hotel, Autograph Collection is a 2-star boutique property featuring 83 rooms, including 18 suites, with nods to its past as the home of WFLA, the area’s first radio station. The hotel’s Hi-Fi Rooftop Bar offers sunset views, craft beers, and specialty cocktails like the Hi-Fi Painkiller and Caladesi Sunset. HEW Parlor & Chophouse serves dishes such as wild boar chops, shrimp and grits, and a Scottish egg breakfast. Guests can relax by the resort-style pool or explore nearby Caladesi and Honeymoon Islands, both ranked among the world’s top beaches. The property is separated from the intracoastal waterway by Edgewater Drive and is 6 miles from Clearwater Air Park. A continental breakfast is available each morning at Fenway Hotel.

Pros

The Hi-Fi Rooftop Bar provides prime sunset views and locally-inspired cocktails.

Proximity to Caladesi and Honeymoon Islands, renowned for pristine beaches and hiking trails.

HEW Parlor & Chophouse offers a distinctive dining experience with dishes like wild boar chops.

The historic lawn hosts outdoor activities and events, including badminton and croquet.

Free bike rentals allow guests to explore the Pinellas Trail, a 40-mile urban pathway.

Cons

The pool lacks heating and may be cooler in certain seasons.

No on-site parking is available.