Concierge.com's insider take:
Originally built in 1923 by pineapple pioneer James Dole for company VIPs and guests, this historic property became Lanai's first hotel. Details such as hardwood floors, ceiling fans, pineapple-shaped bedside lamps, hand-stitched quilts, and vintage photographs evoke the bygone era. Its up-country location is about eight miles from the beach, but you'll get a more authentic feel for local life here than you will at the island's two over-the-top resorts, the Lodge at Koele and Manele Bay. Attentive, friendly service, out-on-the-porch tranquility, and the island's most popular restaurant—the lively Lanai City Grille—make this affordable 11-room inn a real gem. (For the most privacy, rent the original caretaker's cottage.) Being a stroll away from Lanai City center and Dole Park's shops and restaurants doesn't hurt either.