Finding the best Airbnbs in Italy is no easy job—there’s an almost absurd number of beautiful places to choose from, whether you’re after a weathered stone farmhouse surrounded by olive trees, a colorful apartment above a village piazza, a cliffside villa overlooking the Mediterranean, or a centuries-old home where the original tile and shutters have somehow survived. After traveling through Italy in the off-season, including chasing trains between the five towns of Cinque Terre and visiting friends in Puglia, some of my favorite memories are the most low-key: lingering over coffee, wandering into a tiny market, coming home to our rental with a bag of tomatoes and bread, and then opening every window in the house as the evening breeze rolled in.