A private garden with brick walkways, tropical plants, and a canopy of palms sets this convivial guesthouse apart from the pack. The vintage-1880s Island City House has wraparound verandas, pine floors, and charm to spare. Arch House, a former carriage house, has a dramatic entry that opens into a lush courtyard. Although all suites front on busy Eaton Street, only Nos. 5 and 6 face it. A reconstructed cigar factory has become the poolside Cigar House, with spacious rooms, porches, decks, and plantation-style teak and wicker furnishings. The private tropical garden wraps around a spacious pool area. Children are welcome—a rarity in Old Town guesthouses.