6 Best Area to Stay in Key West

Key West, the southernmost city in the continental United States, offers a delightful fusion of sunshine, culture, and positive vibes, all wrapped in an off-the-grid ambiance. So today, we have come up with the best area to stay in Key West.

With its compact size of less than eight square miles, this island is perfect for exploration. It comprises two distinct areas: the contemporary, residential New Town, and the character-rich, historic Old Town, where most visitors spend the majority of their time. The neighborhoods seamlessly blend, making it difficult to identify their borders.

When it comes to choosing accommodations, Old Town, also known as the Historic District, is the top choice.

Whether you opt for a charming bed-and-breakfast in the Heart of Old Town or a luxurious hotel in Downtown, Casa Marina, or the Historic Seaport, you’ll find a suitable place to stay.

Getting around Old Town is a breeze, whether you prefer walking, utilizing the free Duval Loop bus shuttle, or taking advantage of the Old Town Trolley Tours, which offer unlimited reboarding throughout the day.


Affordable ride-sharing services are also available, and due to limited parking, it’s advisable to leave your car at the hotel.

Key West offers a distinctive blend of art, history, and a relaxed waterside atmosphere. While there are other Florida vacation spots more focused on beaches, Key West still provides options for enjoying the sand and dipping your toes in the water.

The breathtaking horizon sunsets alone make a visit worthwhile, especially when observed from the lively Mallory Square street celebrations that take place daily.

The locals take pride in their independent identity as part of the “Conch Republic” while embracing a “One Family” mentality that warmly welcomes people from all demographics, creating an organic and effortless sense of community.

Just be prepared for passionate debates over whether Key Lime Pie should be topped with meringue or whipped cream.

Additionally, you may notice an unusually large number of cats and chickens freely roaming the sidewalks. Embrace this unique aspect of Key West as these delightful creatures have been part of the city’s charm for years.

Best Area to Stay in Key West

1. Heart of Old Town – Best for Walking

The Heart of Old Town stands out as the area where preservation guidelines are most stringent, showcasing a plethora of vibrant wooden structures dating back to the 1800s.

Take a leisurely wander and marvel at the vintage homes that seem to grace every corner, creating an atmosphere akin to a charming bed-and-breakfast haven.

One notable attraction is the former residence of Ernest Hemingway, which has been transformed into a museum.

Whether you prefer to explore independently or join a guided tour, it offers a captivating experience. The above-ground cemetery, surprisingly cheerful in its ambiance, remains in operation but welcomes tourists.

It’s not uncommon to spot joggers and bicyclists passing through, adding to the lively atmosphere.

The Heart of Old Town is an excellent home base, allowing you to reach neighboring districts within minutes by foot. So set off on a delightful stroll and relish the charm that surrounds you. These are reasons which make the Heart of old town the best area to stay in Key West.

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2. Truman Annex – Best for History Buffs

The highlight of the Truman Annex is the former winter retreat of President Harry Truman, which stands today as Florida’s sole presidential museum.

Known as the Truman Little White House, this historical site retains much of its original decor and furniture, offering a fascinating glimpse into the past.

History enthusiasts can explore the museum and indulge in the presidential-themed offerings available at the on-site gift shop. The backyard of the Little White House frequently hosts events, adding to its allure.

As you make your way toward Mallory Square and the Historic Seaport, you’ll encounter several notable attractions which make the Truman Annex the best area to stay in Key West.

The original headquarters of Pan Am Airlines, now transformed into the aviation-themed First Flight Island Restaurant & Brewery, pays homage to the pioneering spirit of aviation.

The Aquarium, Mel Fisher Maritime Museum, and the Audubon House also dot this route. The Audubon House, frozen in time since 1840, presents a unique charm with its spacious courtyard and garden, a rarity within the neighborhood.

Exploring the Truman Annex allows you to delve into the rich historical and cultural tapestry of Key West, with the Truman Little White House serving as a captivating centerpiece amidst a collection of intriguing landmarks.

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3. Historic Seaport – Best for Boating

Departing regularly from the Historic Seaport, an array of charters awaits, ranging from luxurious yachts to elegant sailboat schooners.

These charters offer an abundance of options, including captivating sunset cruises and exciting day trips for dolphin watching, swimming, or snorkeling amidst the vibrant reefs.

If you haven’t made prior arrangements, take a stroll along the docks, as you may be pleasantly surprised by to find spontaneous discounts being offered.

For a unique and environmentally conscious experience, consider Honest Eco, which proudly operates the Key’s first all-electric charter.

This innovative mode of transportation provides an unusually serene journey, allowing you to appreciate the tranquility of the surroundings.

As a bonus, they offer delightful hand-carved fruit platters, adding a touch of elegance to your excursion.

If you’re seeking a different kind of adventure, the Key West Express provides convenient rides to and from Fort Myers and Marco Island along the scenic west coast of Florida.

This transportation option allows you to explore beyond Key West while enjoying the coastal vistas along the way.

With the Historic Seaport serving as a hub of maritime activity, you’ll find a wealth of charter options to suit your interests, offering memorable experiences on the water.

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4. Downtown/Duval Street – Best for Nightlife

Duval Street, situated at the heart of the Downtown area, pulsates with vibrant energy and serves as the epicenter of entertainment, boasting an array of bars, restaurants, and nightclubs.

When the sun sets, the street comes alive with live performances at renowned venues such as the Smokin’ Tuna Saloon, Hog’s Breath Saloon, Irish Kevin’s, and the historic Sloppy Joe’s, a favored haunt of the legendary Ernest Hemingway.

Sloppy Joe’s has transformed over the years into a bustling party destination with its slushy cocktails and lively atmosphere.

For a dose of jazz and blues paired with irreverent charm, head to the Green Parrot, where you’ll xbe greeted by their signature “Sorry, We’re Open” sign.

Rick’s offers a unique experience with its eight bars under one roof, featuring an upstairs nightclub, a downstairs rock bar, and an adjacent strip club.

The intersection of Duval and Petronia marks the Pink Triangle, a vibrant LGBTQ-friendly district, where you’ll find an assortment of party spots, including 801 Bourbon Bar, New Orleans House/Bourbon St. Pub, and Aqua Nightclub, all serving up abundant entertainment and a welcoming atmosphere.

Notably, New Orleans House is renowned for hosting the famous red shoe drop on New Year’s Eve, a celebration not to be missed.

Duval Street stands as a dynamic and diverse hub, beckoning visitors with its plethora of establishments that promise an unforgettable nightlife experience in Key West.

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5. Casa Marina – Best for Hitting the Beach

This district proudly encompasses the Southernmost Point of the Continental United States, an iconic landmark that practically demands a photo stop.

It also boasts the exquisite historic Casa Marina hotel, adding to its allure. Furthermore, the neighborhood is in close proximity to several public beaches located on the southern end of the island.

These include the expansive Smathers Beach, the smaller yet charming Higgs Beach, and the delightful Dog Beach, where pet owners can enjoy the company of their furry friends while savoring cocktails on the deck at Louie’s.

On the other side, the western coast is dominated by the captivating Ft. Zachary Taylor State Park Beach.

This secluded gem offers a more tranquil and serene environment, often attracting locals seeking a peaceful coastal getaway.

While Smathers Beach may draw larger crowds, Ft. Zachary Taylor State Park Beach offers a more intimate experience and a cherished sense of community.

In this neighborhood, you’ll find a delightful blend of historic landmarks, stunning beaches, and hidden retreats, making it a must-visit destination for both locals and visitors alike.

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6. New Town – Best for Families

After a day filled with exploring the various sites and attractions, families often seek solace in the tranquil and modern atmosphere of New Town in Key West.

This section of the city offers a serene escape from the bustling streets. Familiar chain stores and supermarkets are readily available, ensuring that you can easily stock up on groceries and other supplies during your stay.

When it comes to accommodations, New Town is known for its hotels that provide ample space and a peaceful ambiance, all at great value.

A prime example is Parrot Key, a unique hotel situated on a lush, tree-lined five-acre property. Originally a residential townhome community, this hotel has been beautifully renovated to offer guests a comfortable retreat.

One of the standout features of Parrot Key is the option to combine first and second-level rooms, creating shared accommodations that are perfect for large groups or families with children.

This opens up plenty of space and ensures everyone can stay together during their visit. For an even more luxurious experience, you can opt for a room with access to the enclosed beach area.

Fall asleep while swaying gently in a hammock between palm trees, creating a peaceful and dreamy environment for a restful night’s sleep.

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We hope you found our article on the Best Area to Stay in Key West helpful and informative. Feel free to share it with your fellow travelers who will be joining you in Key West. Also, be sure to explore other articles on various travel topics available on IntendStuff. Happy travels!

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