14 Best Hotels in the Florida Keys, From Private Islands to Beachy Bungalows

"With a fascinating history dating to 1946, Islamorada’s Cheeca Lodge has hosted the who’s who of politics, Hollywood, and fishing royalty over the decades, most notably President George Bush Sr. in the 1980s and 1990s (who, in fact, for ten years hosted “The George Bush Cheeca Lodge Bonefish Tournament.” ) Accommodations are spread across a massive campus and vary greatly by enclave. The most coveted units include the Premiere Oceanfront Suites of the 43-room Premier Tower, completed in fall 2022, as well as the Casitas, a collection of 11, two-bedroom stand-alone villas, which share their own beach, tennis court, and swimming pool. Thanks to a long stretch of sandy beach, three pools, a 9-hole golf course, and extensive programming, there’s never a shortage of things to do in the greater Cheeca resort. However, given that it houses the longest pier in the Florida Keys—and fishing rods and bait are complimentary—a preferred activity among repeat guests entails languid days at the ocean’s edge, beer in hand, trying to reel in a catch." - Paul Rubio, Nancy DePalma