Drive south from Miami and you’ll discover an intriguing collection of islands strung together like a shell necklace. Each Florida Key has its own personality, so whether you lean more rugged, refined, or raucous, there is one to match your mood.
First up, Key Largo: Sure, it’s littered with kitsch, but don’t let that dissuade you. Turn off the main highway and you’ll find some terrific spots for relaxing by, in, and under the water. Or cruise down to more sophisticated Islamorada, where fine dining and purple-hued sunsets compete for your attention, along with a host of resorts. Then, keep heading all the way south to Key West to discover legendary characters, a fierce independent streak, and festive fun. Just like the islands themselves, you’ll discover a variety of unique hotels and resorts along the way, from sprawling and intimate to laidback and luxurious; it’s all here in America’s Caribbean. Here are the best places to stay in the Florida Keys.
Read our Key West travel guide here.
Every hotel review on this list has been written by a Condé Nast Traveler journalist who knows the destination and has visited that property. When choosing hotels, our editors consider properties across price points that offer an authentic and insider experience of a destination, keeping design, location, service, and sustainability credentials top of mind. This gallery has been updated with new information since its original publish date.
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