Another charmer of a variation on the Key West theme of historic architecture and a fetching heated pool set amid palmy verdant gardens. Behind a striking, balustraded, triple-decker facade, Island City House also brings a particular distinction to the table: It’s the island’s oldest still-operating guesthouse, established in 1912 from a merchant’s home built in 1880 (if you’re looking for period decor, the original building is the place, with hardwood floors, lace curtains, wainscoting, four-posters, and antiques). Two adjacent, also historic buildings were added and now house half of the units, which lean toward a more contemporary flavor; some, for example, with white pickled-wood paneling, others with a more Tommy Bahama/rattan vibe. It’s also great for folks who want to do a little cooking, as all have full kitchens. Here kitties are part of the scenery, and currently four of them, with names like Blackie and Mr. Toes, get fed through a cute cat-shaped hole next to reception.