Where to stay in the Florida Keys depending on your interests

Published Date: January 6, 2023

Aerial view of the Florida Keys
Just a hop, skip and a jump from mainland Florida but a world away are the picture-perfect Florida Keys. Made up of a 125-mile-long island chain connected by 42 (yes, 42!) bridges, the Keys offer an incredibly wide range of activities and amenities — and where you should stay depends on what you’re interested in. Check out this helpful guide to navigating the 800+ islands in this storied archipelago.

Weekend warriors

The Florida Keys go on and on — Key West is not only the southernmost point in the United States, but it’s also closer to Cuba than it is to mainland Florida. But what if you’re coming from the mainland and only have a few days to spare? Consider Key Largo. It’s just an hour south of Miami and offers plenty of Keys charm. You can snorkel and dive in John Pennekamp State Park, do some sportfishing, and enjoy fresh seafood served up at colorful local restaurants. (If you haven’t tasted conch before, now’s your chance!) 


Marathon is a 10-mile chain of islands located in the middle of the Florida Keys, and it’s a must-visit for families. Young nature lovers can enjoy interactive experiences at the Turtle Hospital and the Dolphin Research Center. They may even get a chance to swim with dolphins! Marathon is also home to family-style resorts and plenty of kid-friendly restaurants. 

Underwater adventurers

The whole archipelago sits along the Florida Reef, the third-largest coral barrier reef in the world. From Key West to Key Largo, world-class snorkeling and scuba diving spots abound. Located in the Middle Keys, Alligator Reef wows divers with crystal-clear waters and amberjack, angelfish, barracuda and nurse sharks. From Marathon Key, divers can explore the Thunderbolt, a military ship that was intentionally sunk in 1986 to become a dive destination. Some 115 feet below sea level, it is now covered in colorful sponges, coral and hydroid. Alternatively, Islamorada’s Hen & Chickens Reef is the best place to see unique coral formations, some 15 feet high. 


With warm, tropical waters come incredible sportfishing opportunities. Islamorada is the self-proclaimed Sport Fishing Capital of the World. Amateur and expert anglers hook everything from bonefish to tarpot to sailfish in this island’s waters. From Big Pine Key, anglers in search of seasonal mahi mahi can book a charter that will give you the best possible chance of catching these prized tropical fish. (Hint: Spring is the peak season for big fish!) 

History buffs

Shipwrecks, pirates and hurricanes, oh my! The Florida Keys have a storied history, making the archipelago a dream destination for history enthusiasts. The best place to start is the Florida Keys History & Discovery Center in Islamorada, with exhibits on the indigenous people who first called the islands home, Spanish treasure fleets, the story of Henry Flagler’s Over-Sea Railway, and more. You may also be interested to know that iconic playwright Tennessee Williams and novelist Ernest Hemingway both called Key West home and both have museums dedicated to their legacies. 


If you’re looking to (really) get away and reconnect with the one you love, head all the way to Key West. Whether your idea of a romantic getaway is a quaint bed and breakfast or a luxury resort, Key West has it all. Spend relaxing days bicycling through Old Town Key West, wander through the Key West Butterfly & Nature Conservatory, take a sunset sail (with wine, of course), or snap selfies at the Southernmost Point Buoy, the southernmost point in the continental United States. You’ll also want to make time to share a slice of key lime pie, of course. 

Discover your perfect Florida Keys retreat

Browse Pacaso listings in the Keys, and discover the better way to own a second home. As a Pacaso co-owner, you can simply arrive on your favorite island, unpack and relax. We take care of the management, maintenance and more.  

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Jen Lyons

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