Drive south from Miami, past Florida City, and the scenery quickly shifts from big-box stores and suburban sprawl to mangroves, sea, and sky. The multi-lane turnpike gives way to two-lane bridges—slender ribbons of road suspended between the Gulf of Mexico and the Atlantic Ocean. So begins the 120+ mile journey to and through the Florida Keys, across 42 bridges and through a captivating chain of islands strung together like a shell necklace. Each Key has its own personality, so whether you lean barefoot and wild, quietly refined, or unapologetically festive, there’s one to match your mood.
First up, Key Largo. Yes, it’s dotted with kitschy roadside stops, but take a turn off the highway and you’ll find quiet coves, coral reefs, and a mellow, water-loving pace. Just beyond, Islamorada shines with fresh-caught seafood, world-class sport fishing, and those famed violet sunsets (the island’s name, after all, means “purple” in Spanish). Soon, revel in 360-degree water views as you cross the famed Seven Mile Bridge, connecting the Middle Keys to the Lower Keys. Upon landfall, keep an eye out for blink-and-you’ll-miss-it Little Torch Key, the launch pad for America’s most coveted private island escape: Little Palm Island. Closer to the end of the archipelago and just north of Key West, Stock Island offers a grittier, more local vibe with working docks and a growing number of upscale surprises.
And, finally, there’s Key West. Its anything-goes energy, sun-faded charm, and fiercely independent spirit have drawn wanderers for generations. Though connected to the mainland since 1938 by US Highway 1, the so-called “Conch Republic” has always marched to its own beat and even once tried to succeed from the US. Here, guesthouses and grand resorts coexist on an island that still feels a little like its own country.
Just like the islands themselves, the Florida Keys are home to a wide range of places to stay—from intimate hideaways to luxe, full-service resorts. Here, we present fifteen of the best.
Read our Key West travel guide here, which includes:
How we choose the best hotels in the Florida Keys
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.
