Drive south from Miami and you’ll discover an intriguing collection of islands strung together like a necklace of shells. Each Florida Key has its own personality, so whether you’re more rugged, refined, or boisterous, there’s one to match your mood.

First, Key Largo: Sure, it’s littered with kitsch, but don’t let that deter you. Get off the main highway and you’ll find great places to relax near, in and under the water. Or cruise to more sophisticated Islamorada, where fine dining and purple-hued sunsets vie for your attention, along with a host of beach resorts. Further south, Duck Key attracts families with its summer camp vibe. Then, continue south to Key West to experience legendary characters, a fierce, independent streak of party fun. Much like the islands themselves, you’ll discover a variety of hotels and resorts along the way, ranging from sprawling and intimate to laid-back and luxurious; it’s all here in the American Caribbean. Here, the best places to stay in the Florida Keys.

Read our Key West travel guide here.

This gallery has been updated with new information since its original publication date.

All listings featured on Condé Nast Traveler are independently selected by our editors. If you book something through our links, we may earn an affiliate commission.