Find exclusivity on a secluded 27-acre island that’s home to Sunset Key Guest Cottages (from $495), a 40-cottage resort that’s just a five-minute ferry ride from Key West. If you’re traveling in a group, book one of the newer three- and four-bedroom colonial-style cottages with private pools. Book a Swedish massage (from $80) at the new spa, then decompress on your treatment suite’s individual patio.
Walk steps to the Gulf of Mexico at The Reach (from $179), the only property on Key West with a private natural-sand beach. Stay active by renting a variety of water-sports equipment (from $25) or attending morning yoga on the adjacent Casa Marina pier ($20), or lie back and enjoy poolside service from the hotel’s Strip House outpost.
Experience the island’s quirky side two miles away from historic Old Town at the fifties-era Ibis Bay Waterfront Resort (from $139), which was renovated and reopened last year. Enjoy the 600-foot stretch of sand (in the process of being extended) with jet-ski and kiteboard rentals (from $25 per hour) from the fun desk, or do something new and get a lesson in sand sculpture ($49 for two-and-a-half hours) from local artists Marianne van den Broek and Chris Guinto.