1. Up Country Hawaii by Cullman & Kravis—Ellie Cullman designed this refined Hawaiian retreat for Oprah Winfrey. Instead of taking the tropical route, Cullman used traditional American furnishings and decor to create a truly singular and unexpected island getaway. The bright and airy residence features an abundance of natural materials, including rich woods, wicker, and stone, which reinforces the home’s connection to its lush surroundings.