Islamorada, often called the Sportfishing Capital of the World, offers a string of waterfront resorts along the scenic Overseas Highway. These properties range from the 27-acre Cheeca Lodge & Spa, with its 9-hole golf course and 525-foot fishing pier, to the family-focused Three Waters Resort, which spans 15 oceanfront acres and includes a dedicated adults-only enclave at The Cove. Travelers can expect amenities like multiple swimming pools, private beach areas, and on-site dining-all within easy reach of attractions like John Pennekamp Coral Reef State Park.
Budget-wise, expect to pay anywhere from $250 to $600+ per night depending on season and room type. For a more intimate experience, the boutique Pines & Palms Resort (scoring 93/100) offers fully equipped kitchens and direct beach access, while Islander Resort provides a classic Florida Keys feel with two pools and a private beach. Families should consider Three Waters for its included paddleboards, kayaks, and bikes, while couples can retreat to the adults-only Cove area. For the best value, book mid-week and consider the shoulder seasons (April-May, October-November) when rates drop.