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May 17th
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A Guide to the Most Unique Neighborhoods in Key West, Florida

If you are ready to explore somewhere new, then you can't miss this guide to the unique neighborhoods of Key West, Florida. Despite this small island only being two by four miles, it's home to a collection of diverse and beautiful neighborhoods. While the parameters are subtle, each area offers unique architectural styles, character, and historic interest. So, the next time you visit, venture beyond the tourist-packed streets and experience what island life is like for the residents for the southernmost United States.

Plan to visit the unique neighborhoods and take in their highlights during your next visit to Key West, Florida.

Old Town


As the name implies, Old Town is the historic district of Key West. You'll find the famous Mallory Square that comes to life at sunset with performers and streets stalls. Other Key West neighborhoods are also located in this district, including Bahama Village, the Meadows, and the Key West Historic Seaport.

Famous landmark in Old Town Keywest Ice Cream Sign

Old Town is the perfect place to start your visit to Key West. Grab a drink at the famous Sloppy Joe's and a slice of key lime pie to delight your taste buds. Then check out the rich history of the island with pirates, gold hunters, and the home of Nobel and Pulitzer Prize winning author Ernest Hemingway.

If you're looking to stay in the heart of Old Town, you'll find stunning Victorian homes and cottages. You'll love the adorable names of the narrow streets, such as Poorhouse Lane and Love Lane. It gives you a real sense of what life was like for the early shipbuilders that called this area of the island home.

Downtown


If you're looking to stay in the heart of the action, then you'll want to stay downtown Old Town. This is the main strip of Duval street between Mallory Square to the north and the southernmost point to the south. There are bars, restaurants, hotels, shopping, and plenty of entertainment to keep you busy.

tropic cinema downtown key west

downtown key west fl

 

 

Uptown


Did you know that Key West was a prominent cigar factory town in the late 1800's? Driven by Cuban immigrants, a prominent businessman, Eduardo H Gato, built a stunning marble building on Simonton Street, to manufacture cigars. The building was completely renovated and now houses local government offices. Most of the historic wooden cottages and houses, originally built for cigar makers, have been renovated into charming homes. Many are available to rent as vacation rentals.

butterfly conservatory upper duval key west

upper duval street key west fl

 

Uptown encompasses Upper Duval Street where there is an exceptional variety of restaurants, boutiques and furniture galleries. This neighborhood also includes the Southernmost Point of the United States and Key West South Beach.

uptown

Heart of Old Town


In the center of the island is the residential heart. It includes the highest point of the island, Solares Hill, a whopping 14 feet above sea level. Historic streets are lined with gingerbread Victorian houses and cottages built by early shipbuilders. There are many houses and cottages available to rent as vacation rentals.

heart of oldtown key west

 

You’ll find your way here when you go to visit the must see historic Key West Cemetery. A large green space, walking through the cemetery you’ll see interesting headstones and get sense of Key West history. The USS Maine Memorial, honoring the sailors who died the sinking of the battleship in Havana Harbor is in the cemetery.

Bahama Village


On the southwest side of Old Town is the most colorful and cool neighborhoods of Key West. This 16-block neighborhood is one of the oldest on the island, dating back to the 1800s. It was once home for the marginalized people of the Bahamas and the Caribbean who settled on the island.

bahama village key west FL

 

You'll know you're in the right area when you see streets lined with "shotgun" homes with clapboard siding. The homes are colorful canary yellow and Caribbean blue.
Today the neighborhood is home to colorful shops and some of the best restaurants on the island. One of the most famous restaurants, Blue Heaven, is on Olivia Street in Bahama Village. You'll taste some of the freshest seafood you've ever eaten as you're entertained by the free-roaming chickens and cats.

Truman Annex


Did you know there's a naval station in Key West? This active military base is located on the island's southwest side, near the cruise ship ports. When Harry S. Truman was president, he had a winter "white house" located in an annex as a part of this station.
This portion of the property has since been sold to a developer who has turned the once presidential annex into a redevelopment neighborhood in Key West. It includes 425 traditional conch style homes, high-end condos, a hotel, and affordable housing. Truman's house was also preserved and turned into a museum.

fort zachary taylor statepark beach truman annex key west

truman annex street view key west fl

 

Staying in this gated community will feel more like living in a park. The grounds are perfectly manicured, and you'll be able to freely enjoy the picturesque views.

Historic Seaport


You'll find Key West's marine industry and most active ports in the historic seaport. In the middle of the 19th century, this area was a gathering place for commercial fishing, sponging, and shrimping. In the 90s, the area was redeveloped to also be a place for both locals and tourists to enjoy.

historic seaport mallory square key west

historic seaport keywest FL

This is the place to go if you're looking for a boat charter or watersports activities. There are also plenty of restaurants and live entertainment.

New Town


Just as there's an old town chock full of history, there's a New Town that celebrates modern-day Key West. This area was mainly developed in the 1900s and is home to about 75% of the residents of Key West. You'll find homes, shopping centers, schools, and government buildings.

 

Most people consider anything northeast of White Street to be a part of New Town. You'll find the restaurants that the locals frequent and other services that cater to everyday life.

Mid-Town


In between New Town and White Street Gallery, the Mid Town neighborhood is where you can find mid-century Key West homes with larger yards that are beautifully landscaped. Many homes are renovated to become unique island dream homes belonging to full time residents.

Proximity to the beach, White Street, and New Town, many seek out this location to stay. Occasionally houses are available to rent in this neighborhood for a month or more.

The Meadows


When you venture past White Street and into New Town, the first neighborhood you'll encounter is The Meadows. You'll see uniquely wide tree-lined streets and large historic homes. There's a distinctly elegant and gracious feel to the area that will add some class to your vacation.

Staying here will give you a quiet escape from the lively Duval Street while also being close enough to the action to take part when the mood strikes. The area is home to people who live on the island year-round, but there are several homes available for rent. This is a great area to check out art galleries, bakeries, and high-end shops.

White Street Gallery


White Street is the focal point of this neighborhood and is referred by many as the “local’s Duval Street.” Here you’ll find an assortment of locally favorite businesses including food stores, hair salons, yoga studios, veterinarian clinic, and a variety of restaurants.
The author Tennessee Williams once lived in this area, and a variety of art galleries earned it the name White Street Gallery neighborhood. Residential streets are lined with an eclectic collection of houses. It’s central but off-the-beaten path location make it favorite place to stay.

Casa Marina


On the southeast side of the island, you'll find the area known as Casa Marina. It's just north of the Southernmost Point in the Continental US. You'll find high-end hotels with stunning private beaches. If you're looking to enjoy large homes with quiet streets, then this is the area of the island for you.

west martello tower casa marina key west

Even if you aren't staying here, it's worth a visit to check out Higgs Beach, Smather’s Beach, or White Street Pier. These are the perfect place to take a sunrise or sunset stroll along the shore and breathe in the salt air.

Beachside


Beaches stretch all along the south shore of the island and here you'll find residences, museums, and businesses. The Beachside neighborhood feels like a beach town with light ocean breezes, and a paved biking and walking path stretches along the ocean front. Here you'll find ocean front condos, parks, tennis courts, and beachside dining.

beachside key west florida

This neighborhood is also the location of two brick pre-Civil War Forts. Fort East Martello is now an important museum and houses the famous haunted Robert the Doll. West Martello Fort houses the Key West Garden Club. Both are on the U.S. National Register of Historic Places.

Southside Resort


The extreme southeast shore of Key West is the location of several stylish European and Caribbean style resort condominiums and hotel complexes. The airport is close to the hotel complexes that were developed for tourists.
The south end of Smather’s Beach is across the boulevard from the hotels and condos. For a short stay, of a day or two, this can be an affordable and convenient location.

Northside Resort


The main boulevard entering Key West from U.S. Highway 1, is North Roosevelt Blvd. This neighborhood borders harbor side of the island where the waterfront leads out to the Gulf of Mexico. This is were you’ll go to find shopping centers, some chain restaurants, and hotels.

A long-paved path between the boulevard and the seawall is Key West’s own Malecon. Walk or bike along the path to enjoy the view and along the way check out Houseboat Row.

Golf Course Neighborhood


Immediately before driving into Key West you can see the Key West Golf Club on the right side of U.S. Highway 1. In additional to offering a beautifully maintained 18-hole golf course, it is also a planned gated residential community. Here you find townhomes and luxury villas, many with views of the Golf Course greens.

A quiet and peaceful neighborhood, golf paths and narrow streets wind through manicured grounds with white picket fences, making this a great place to relax and rejuvenate. Rentals in this neighborhood offer a great value for a quality experience.

Sunset Key


For the traveler who is looking for ultimate luxury, Sunset Key is a 27-acre private tropical island surrounded by turquoise waters. It is located 500 yards off the main island of Key West and accessed by a small ferry boat. This is a 5-Star Resort island, including a luxury hotel, award winning Latitudes Restaurant, resort amenities, and white sandy beaches.
From here you’ll experience some of the most breathtaking sunsets in the world. Impeccably manicured grounds with mature landscaping and aged brick paths wind along the front yards of a distinctive collection of elegant multi-million- dollar homes. Several private homes are available to rent for a month or more. A few have gardens that lead directly to a private beach.

Experience Life in Key West, Florida Neighborhoods


As you can see, Key West, Florida is full of history, culture, and a vibrant love of life. You'll find colorful buildings and people as you stroll around the tiny island. So, the next time you visit, venture beyond Duval Street and the tourist attractions and experience the diverse communities that call these Key West neighborhoods home.
Book your vacation home today and plan your next trip to Key West.


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