Key West is a magical island that blends the beauty of the Gulf of Mexico and the wild rush of the Atlantic Ocean with a real sense of history and serenity. Whether you stay in Key West itself with its fine dining options and resort lifestyle or choose a Key West vacation rental on a more secluded island nearby, you’re sure to return from your holiday relaxed and happy. Here are 10 of our favorite places to stay near Key West.

1. Old Town, Key West

old town

In Key West’s Old Town, you can experience tropical luxury combined with fabulous restaurants and shopping. Surround yourself with magical beauty when you visit the Key West Butterfly and Nature Conservancy, and then stroll down Duval Street to explore intriguing gift shops, boutiques, and art galleries. At the end of the day, relax in your cozy cottage with a hot tub on the patio, or look out over Duval Village from your penthouse that puts you above it all.

2. Truman Annex, Key West

hemingway house

This exclusive neighborhood, which puts you right on the water at the far end of the island, has some unique ties to history. Visit the Ernest Hemingway Home and Museum and Harry Truman’s Little White House to learn about some of the most famous residents of this remote island. You can even stay in a piece of history when you rent a historic home that dates back almost 150 years and is large enough to accommodate your whole family or choose an oceanfront condo that offers stunning sunset views.

3. Midtown, Key West

palm trees

In Midtown, stay in a condo that sits right on the water with a spectacular view of the Atlantic Ocean, or opts for a spot in a private community with immediate access to the Key West Nature Preserve. Head to the eastern side of the island for some peace and quiet. Take a picnic to Smathers Beach to relax under a palm tree and snap photos that are as perfect as any postcard.

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4. Newtown, Key West

cruise ship

Sail up to the Newtown neighborhood of Key West and dock your boat at the boat slip available at your vacation condo. A visit to the Fort East Martello Museum provides fascinating insights into the cigar-rolling, sponge-collecting past of the island, and boat tours can take you scuba diving, snorkeling, dolphin or shark-watching, or just sailing into the spectacular sunset.

5. Stock Island

stock island

Stock Island, which serves as the gateway island to Key West, is home to the Key West Tropical Forest and Botanical Garden, one of the few spots in Key West where you can still experience the island in its natural state. The many marinas of Stock Island are also a great jumping-off point for boat tours of the Keys and scuba and snorkeling trips. Stay on the water at night when you rent a houseboat as your home base, or pamper your whole family with a palatial oceanfront estate with a private beach and boat dock.

6. Sugarloaf Key

key west bridge

Privacy and beauty are the hallmarks of Sugarloaf Key. Treat yourself to a lifestyle few get to experience when you stay in a vacation home on a private beach in the middle of a wildlife preserve, slipping off your private dock to snorkel and swim in the clear water. Charter a boat to take you fishing on the ocean, or enjoy a private kayak tour that lets you see the wildlife of the islands in a new and fascinating way.

7. Cudjoe Key

lighthouse

Enjoy eco tours, jet ski rentals, chartered fishing trips, and sailing from your vacation rental on Cudjoe Key, and set aside some time to get pampered at one of the local spas. Sail your own boat up to an ocean front dock, or relax in a hammock outside your vacation condo. Don’t miss the giant bat tower in the middle of the Key.

8. Big Pine Key

beach sunset

Relax on the white sand beaches of Bahia Honda State Park and Beach, or visit the unique National Key Deer Refuge when you enjoy the uncrowded lifestyle of Big Pine Key. Beachfront homes with screened porches for dining and easy access to both the Gulf and the Atlantic Ocean add to the comfort of your stay.

9. Marathon Shores

beach sunset

Vacation in luxury and privacy in an oceanfront estate on a private island just off Marathon Shores, or pick a spot near Sombrero Reef with a private boat dock and expansive ocean views. Helicopter tours taking off nearby let you get a sense of the entire stretch of the Keys. Once you’re back on the ground, pay a visit to the Turtle Hospital to see the good work local veterinarians are doing to rescue sea turtles and pick up a friendly concert put on by the Florida Keys Concert Association.

10. Key Colony Beach

man fishing

Sports fishing is a big deal at Key Colony Beach, but don’t forget about the wonders under the water as well. Bring your snorkel or scuba gear to Collins Patch, just off the key, to enjoy spectacular underwater sights. Your vacation rental here might be a cozy condo overlooking a white sand beach filled with tiki huts to provide a little shade or choose a home on one of Key Colony’s wide channels where you can catch fish off your own dock and grill your haul for dinner.

 
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