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Just 106 miles from Havana Cuba, Key West is America’s southernmost point and is steeped in Spanish history. To get here, you’ll need to cross over 42 bridges and drive 126 miles from the mainland or fly into Key West International Airport. The island's land mass is only four miles long and one mile wide yet it is one of the most exciting and relaxing places to live in Florida. 



Authors, musicians, vacationers, newlyweds, roosters and a few cats

Key West residents have a carefree spirit and deep appreciation for being disconnected from the rest of the world. Most have dark suntans, permanent smiles and a somewhat a hippy attitude. Affluent empty-nesters with disposable income blend in discreetly with those living pay check to paycheck. There are just as many year round residents as second home owners. 

The population of Key West is around 25,000 people and swells to double that during major week-long events such as Hemingway Days, Conch Republic Independence Celebration, Key West Power Boat Races and Fantasy Fest. Key West has been recognized as the #1 wedding destination by Trip Advisor.



Lots of tourists, pastel architecture, streets filled with bicycles and live music 

Cruise ships come and go daily at Mallory Square with over one million passengers visiting the island annually. The Naval Air Station Key West is an active training base and airport. There are a few more big box stores in Key West compared to the rest of the Florida Keys. Those include Office Max, Ross, TJ Maxx and Sears. Two public marinas on the island are Key West City Marina and Key West Bight Marina. Key West Golf Club spreads across 200 acres and has a Rees Jones designed course. 

Old Town is Key West’s first residential neighborhood and is less commercial. The Key West Historic District includes Duval Street, Mallory Square and Truman Annex. The Meadows on the north side of the island is also residential. Sunset Key is the exclusive residential neighborhood across the Key West harbor and is only accessible by ferry.  Key West also has houseboat communities all around the island. Parking is limited, but Key West’s city bus is inexpensive and makes travel easy to get around the island. The cost of living overall is higher because everything has to be imported.


Key West has four distinct beaches: Fort Zachary Taylor, Smathers Beach, Higgs Beach and South Beach. Most have water toys, restroom facilities and dining nearby. The Truman Waterfront Park Amphitheater is a cutting-edge, new multi-million dollar outdoor concert facility near Ft. Zachary Taylor State Park with a 3,500 seat capacity and plenty of space on the grass-filled grounds to enjoy the show lounging on a lawn chair or laying out on a beach towel. Fort Jefferson at the Dry Tortugas is a gorgeous national park about 68 miles from the Key West harbor. It is a popular boating hangout for those who have boats that can make the trip.



Historic homes, conch houses, timeshares, new condos here and there 

Pastel-colored Antebellum homes, as well as old mansions, with white picket fences and tropical flowers in bloom along the sidewalks, add to the island’s curb appeal. You’ll find homes dating back to the early 1900s beautifully restored to their original grandeur. There are approximately 10,000 homes on the island. All the homes have mandated metal roofs and parking is limited. 

Fixer-upper single-family homes start in the $400s, golf villas in the $500s, small condos start in the $300s and range to well over $1 million for new Key West condos and townhomes.  The average sold price on the island is around $700,000.

The city of Key West regulates vacation rentals. No new licenses less than 30 days are issued, but homes with existing licenses, may rent their homes less than 30 days. Be sure to check with the city before purchasing if you intend to use the home as a vacation rental. 

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A rich history of shipwrecks, sunken treasure and President Harry Truman’s influence on the island

Salvaging shipwrecks on coral reefs was the main occupation in the Florida Keys through much of the 19th century, helping make Key West the biggest and richest city in Florida. Like a time capsule, the shipwrecks and tales of distress remind us of how difficult it was back then to navigate the shallow Florida Straits without a digital GPS.

In the 1940’s Harry Truman spent a good amount of time in Key West during the winter months enjoying the warm weather. The Little White House, where he resided, remains a picture-perfect neighborhood with white picket fences, posh two-story residences and lush tropical foliage.

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Removed, relaxed, intentional and ‘anything goes’ attitude

Life in the tropical paradise of Key West, is enviable. Most non-residents spend all year working and saving money to grab one week in paradise while folks who live in Key West, live the dream every day. Biking to work, catching the best happy hours, enjoying the night life, and protecting Key West’s uniqueness. The locals and the tourists from around the world live harmoniously.

There’s also a sweet appreciation between the locals and the Key West businesses. On the first Sunday of the month, some attractions are complimentary to Monroe County residents, and discounts are offered on food, attractions and services. Locals return the love by shopping and dining on the island. Conchs, or Key West natives, have a strong and undeniable spirit.

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Conch Republic Independence Celebration - April

Hemingway Days Festival - July

Bahama Village Goombay Festival - October

Fantasy Fest - October

Key West Power Boat Races - November

New Year’s Eve in Key West - December

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Vibrant colors, fragrant smells, ocean breezes, and the quirkiness of it all

The variety of museums, art galleries, historic homes and incredible foodie scene is incredible. The endless live entertainment from Jimmy Buffett cover bands to Diana Ross and The Supremes look-a-likes at the Bull & Whistle will keep you grooving. The pirate vibe, the parrot heads, the rebellious conchs…this list goes on and on. Live like a local, or play tourist for the day--anything is possible in Key West.