A common question for travelers who have never been to the Keys is where to stay in the Florida Keys. The Florida archipelago consists of a 126-mile string of islands surrounded by turquoise water under constant sunshine. While Key West gets a lot of the attention of course but, where to stay in the Florida Keys depends on what you’re looking for. Whether you’re looking for a laid-back beach vacation, a fishing adventure, kayaking mangroves, or spending the late-night hours on Duval Street, this is the guide you’ve been looking for. Just a warning for never-beens, the Florida Keys can get expensive.
Where to Stay in The Florida Keys for Scuba Diving, Snorkeling and Nature: Key Largo
If you’re coming from Miami, Key Largo is about an hour’s drive, depending on traffic. It’s the first Key from the mainland. Once you’re on the island you’ll understand what “island time” is.
Things To Do
Key Largo is the self-proclaimed “Diving Capital of the World” and it’s not hard to see why. Drive down the Overseas Highway and you’ll see dive shops littering both sides of the street. Add to that kayak tours, snorkel tours, and awesome fishing charters just waiting to take you out for a perfect day on the water.
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If you’d rather spend time in wooded nature, Dagny Johnson State Park offers nature trails and backwoods trails to bike and hike. John Pennekamp State Park has beaches, nature trails, fantastic off beach snorkeling, and mangrove tunnels to kayak through. They also offer snorkel and scuba diving tours to the Christ the Abyss statue.
Where To Stay
Favorite places to stay are Gilberts Resort, a small motel with a private beach, fantastic tiki hut restaurant, and water toy rentals. You can drive or boat there, they have dock space available for the day or longer. On the other end of the spectrum is Bungalows Key Largo. Luxurious accommodations featuring private outdoor soaking tubs, and a Zen garden spa.
The Bayside Inn Key Largo covers all your needs with complimentary kayaks and SUPs available. A private beach to relax on, or a pool if that’s more your thing. There’s a dive shop on site and they have stay and dive packages. Oh, and bring Rusty, because it’s a pet friendly resort.
Where to Stay in the Florida Keys for Luxury and Chill: Islamorada
If you’re wondering where to stay in the Florida Keys for laid back island vibes, Islamorada is the place to be. A walkable artsy downtown, a local brewery, fabulous restaurants, and views of Caribbean-esqe waters, all add to the relaxed setting.
Things To Do
Get a little bit of education at the History of Diving Museum, see what one couple turned forty years of collecting diving gear into. Just on the southern side of the Indian Channel Bridge is Robbies. At Robbies, you can grab your bait fish and head out to the dock and hand feed the tarpon. Or you can rent a kayak and paddle over to Indian Key and experience a ghost town. Maybe you just want to pull up a chair and enjoy a fresh seafood meal at their waterside restaurant, you can do that.
If you’re in Islamorada on the third Thursday of the month, head on over to the Morada Way Art District and help support a local artist at their monthly art walk. If you can’t find what you’re looking for there, the Rain Barrel Village will surely have something for you. At the very least, you can get your picture taken in front of the giant lobster.
Where To Stay
If you’re looking for the luxury part of Islamorada, The Islands of Islamorada have four-bedroom villas for about $2,000 a night. Amenities include watersports, poolside tiki bars, bikes, a marina, and a fireside s’mores experience (additional charge).
If you want to dial down the luxury a bit, then Casa Morada is a good choice. It’s mid-island and secluded on the Gulf side so you’ll get your share of beautiful sunsets. Of course they have all the amenities, free bicycles, complimentary breakfast, and even yoga mats.
Another good choice is the Sunset Inn, a small hotel that has recently been updated. Roomy rooms surround the pool. It’s conveniently located close to a marina and is reasonably priced.
Where to Stay in the Florida Keys for Fishing and History: Marathon
To rival Key Largo’s diving claim, Marathon is the self-proclaimed Fishing Capital of the World. But, when you go there and see all the marinas and charter boats, you’ll come to the conclusion that yeah, they have a point.
Things To Do
But Marathon is more than just fishing. If you want to see what the Keys looked like before development, head over to Crane Point Hammock. Not only is there a mid-century house in the middle of a 63-acre tropical forest, there’s also the oldest house in the Keys outside of Key West. Stop in for a fish pedicure, feed the fish at the point, and explore the tropical hardwood hammock and experience what it used to be like to live in the Florida Keys.
Get an education on sea turtles at the Marathon Turtle Hospital. They’ve been saving turtles since 1984. The Turtle Hospital has multiple tanks and pools set up for injured sea turtles that have been operated on, treated for sickness, or need rehab in some way. It’s definitely worth your time to see what the hospital has done for over 1,500 turtles.
On the southern tip of Marathon, that little island just west of the Seven Mile Bridge is Pigeon Key. Pigeon Key was instrumental in building the Overseas Railway and Highway. Now it’s a museum with restored buildings and awesome snorkeling.
If you’re more of a beach person, grab your lounger and head to Sombrero Beach. Soft sand and fabulous views of the Atlantic Ocean are waiting for you.
Where To Stay
If you want to stay someplace that’s a little different, try the Yacht Haven Marina and stay in your own houseboat. You won’t get any closer to the water than this. Each houseboat is a two-bedroom suite that will sleep six.
If you’re looking for a resort, then Hawks Cay Resort is right up your alley. Tailored for families Hawks Cay is on Duck Key and features 5 pools, a private lagoon, restaurants and bars, and you won’t want to miss out on the dolphin encounters.
A nice quiet motel with its own private beach is Blackfin Resort and Marina. They have quaint rooms with a refrigerator and microwave. There’s a chilled pool for when it’s hot, and a private beach to enjoy the sunsets.
If you’re bringing the RV or tent, there are campgrounds at Long Key, Curry Hammock, and Bahia Honda State Parks.
Where to Stay in The Florida Keys for Nightlife, History, and Water Adventures: Key West
While Key Largo and Marathon are laid back and relaxing, Key West is in your face fun and adventure. Historic homes, churches, and lighthouses litter the streets while water activities call you to jump on a boat and explore. Duval Street is a non-stop party with revelers and reveler watchers, while Higgs Beach and Smathers beach beckon you to sit back and re-energize before the next round of fun starts.
Key West is divided into New Town and Old Town. New Town is on the north end of the island where the big hotels and resorts are. Think marinas filled with boats, resorts with every amenity available so that you never have to leave the site. If you do leave, you’ll need a car, taxi, or Uber. Perfect for families who want to enjoy the Tropical environment with the convenience of everything you need at your fingertips.
Things To Do
Old Town is a walkable historic section of town filled with B&Bs, retro motels, and plenty of things to do. If you’re into historic forts and beaches, Fort Zachery Taylor is on the southeast tip of the island. It’s a civil war era fort next to a fantastic beach. Another historic home on Whitehead Street is the home of famous Author Ernest Hemingway, take a tour where he wrote a lot of his most popular books and learn about his six-toed cats. After you’re done there, take a walk across the street and climb the 177-year-old lighthouse and get unparalleled views of Key West.
If you head to the west side at the end of Whitehead Street you can check out The Shipwreck Museum and see what life was like in the 17th century on Key West. Or you can book a kayak-and-snorkel sail on Danger Charters. If that’s not your thing, hit up Fury for a ride on one of their catamarans. After you get back you can stay at Mallory Square and enjoy the sunset with all the other sunset enthusiasts.
Anytime is a good time to take a stroll up and down Duval Street. Restaurants, bars, art galleries, and souvenir shops line the shaded street. After hours the bars really come alive, check out historic bars like Sloppy Joes, Capt. Tonys Saloon, and The Green Parrot Bar. The drag shows are non-stop at bars like 801 Bourbon Bar, or the Aqua Nightclub. Let it all hang out, literally, at the Garden of Eden, Key West’s clothing optional bar. And finally, end the night at one of the many cigar bars that are on Duval Street.
Where To Stay
The Hyatt Vacation Club is a beautiful property on the beach. Close to the Martello museum and Smathers beach, if a private beach isn’t your style. There’s a restaurant on site, for those nights when you don’t want to go out.
Havana Cabana is a quirky hotel with plenty of amenities and the largest pool in Key West! If you’re in the mood for good food, their very own Cuban style food truck is waiting for you, you’re not going to want to miss those Empanadas.
For the B&B lovers, you’ll find yourself in the Old Town section, Winslow’s Bungalows on Truman Street is a historic inn conveniently located to Duval Street, but far enough away to keep the noise at bay. You have your choice of three pools to relax by, or you can hang out at the onsite Bungalow Bar and enjoy a cocktail.
The Conch House is also on Truman; it’s a little closer to Duval Street but still far enough away to miss the noise. This 19th-century Victorian home is now a top-rated B&B and is owned by direct descendants of Key West settlers. The three houses onsite all have wrap around porches to enjoy the night breezes. There’s a pool and they offer off-street parking for $10 a day.
The Southernmost Beach Resort is accurately named; it’s located at the end of Duval Street right next to the Southernmost Buoy. Only stay here if you’re into two private beaches, three pools, private cabanas, spa, a fitness center, and luxury accommodations.
Now that you have an idea where to stay and what to do, it’s time to start packing, the Keys are calling.
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