Round Hill, Jamaica For a hotel that’s part-owned by Ralph Lauren (who designed the rooms), this boutique Jamaica gem somehow remains something of a well-kept secret. Round Hill, which opened its doors in 1952, has managed to retain its timeless ambience, instantly transporting you to the dawn of the jet-set age the moment you ride down the hill to the lobby. And history is at the core of this place, where boldfaced names from half a century have all stayed, from John F. Kennedy (yes, you can stay in his villa) to Oscar Hammerstein.