With a city this appealing, you’re going to want to stay awhile. The elegant and historic Fenway is a stellar choice, with its calm and cozy rooms, as well as a rooftop bar with a fabulous view of the water. In keeping with Dunedin’s small-town attitude, the city has several B&Bs to choose from, including the Meranova (where each suite has a private entrance, bath and kitchenette) and Beyond the Wall Bed and Breakfast (as they explain, offering a retreat for “beachgoers and bohemians of all backgrounds”).
At the Best Western Plus Yacht Harbor Inn, every room has a view of St. Joseph Sound - and there’s easy access to sightseeing and charter fishing boats, as well as Bon Appetit restaurant.
Looking for vintage digs? Palm Court Motel was built in 1957 and definitely delivers on that Old Florida feel - plus it’s the closest hotel to Honeymoon and Caladesi islands. Seaside Artisan Motel is another good retro option - and it gets extra points for being both pet-friendly and within walking distance to downtown Dunedin.