Best Areas to Stay in Key West Pin 4

Going to the Southernmost U.S. City and wondering where to sleep?

On this list, you’ll find the 7 best places to stay in Key West for first-timers, party goers, culture vultures, families, solo travelers, and anyone in between.

  • Wanna stay close to the beach?
  • Perhaps party the night away?
  • Or would you rather wake up to the sight of famous Key West attractions?

Either way, we have you covered.

Despite its compact size, the island town offers unique experiences to all kinds of travelers.

Hop on and find out where to stay in Key West.

1. Stay in Key West Historic District for the 100-Year-Old Victorian Mansions

Hemingway House and Museum
Stay in the Historic District for the Victorian mansions, such as the Hemingway House and Museum

The Historic District or Key West’s Old Town covers most of the city’s area.

Between the seashore and the streets Angela, White, and Whitehead, you’ll find almost 200 historic buildings and structures.

Stay in this area if you fancy Victorian architecture with a touch of Spanish and Bahamian influences.

In the Old Town, you’ll find The Hemingway Home and Museum, the historic Key West Lighthouse, and the Key West Cemetery.

Don’t miss a chance to count all the chickens you encounter. A funny fact about Key West is that there are more hens roaming its streets than humans.

Our recommendations: The cozy 3* hotels Silver Palms Inn and Kimpton Winslow’s Bungalows will both pamper you with their tropical gardens, cooling swimming pools, and spacious, stylish rooms.

2. Stay between Mallory Square and Key West Bight Marina for the Sunsets, Boats, and Museums

Key West Sunset at Mallory Square
The stunning Key West Sunset viewed from Mallory Square

The area around Mallory Square houses most of the city’s museums. The square itself proudly hosts one of the coolest sunset celebrations you’ll ever experience.

In this neighborhood, you can explore several attractions and quirky museums, such as:

  • The Key West Aquarium;
  • The Shipwreck Treasures Museum;
  • The Mel Fisher Maritime Museum;
  • Truman’s Little White House; and
  • The Key West Museum of Art and History.

Further down the coastline, you’ll also find the historic Key West Bight Marina. Next to it, you’ll discover the interactive Sails To Rails Museum at Flagler Station and the ferry to the Dry Tortugas National Park. Apart from a day trip to the park, you can also hop on a snorkeling tour or a sunset cruise from the pier.

Stay in the area if you wish to watch the boats sail from the historic port or to experience the sunset celebrations.

Our recommendations: Pick the exceptional, spacious holiday home Sunset at Harbour Place for the fantastic views, huge living area, fully equipped kitchen, and outdoor pool. If you prefer luxurious resorts, the 4* Ocean Key Resort & Spa with its exquisite wellness area and quirky rooms in bright colors will charm you.

3. Stay at Duval Street for the Mile-Long Pub Crawl

Duval Street Bar
Bars and pubs line Duval Street and invite for drinks till the wee hours

The 1.25-mile-long Duval Street is the heart of the nightlife in Key West. The road runs from coast to coast. Victorian mansions featuring Bahamian and Spanish influences line its sides.

Most of the travelers who visit the town for more than a day spend at least one evening bar hopping.

Even if you decide to book your lodging away from the hustle of the party mile, you should still visit some of the iconic Key West bars and pubs.

The most famous establishments are:

  • The historic Sloppy Joe’s, Hemingway’s favorite bar in Key West, serving great rums and cocktails.
  • The original Jimmy Buffet’s Margaritaville Café playing nightly live music shows.
  • The lively Flying Monkeys bar which makes arguably the best frozen cocktails in Key West.

Tip: You can also find great locales in Whitehead Street, which runs parallel to Duval Street. For example, check out the Green Parrot Bar, established in 1890.  

If you wish to fall from your chair right into your bed, pick one of the accommodations below.

Our recommendations: If you’re looking for a cozy, unpretentious, and affordable stay, choose the Duval House Bed and Breakfast. You can relax in its gorgeous tropical garden after a long day of exploration or an endless night of partying. And if you prefer more luxurious accommodation, check out the Orchid Key Inn. The modern, spacious rooms, the refreshing swimming pool, and the happy hour at the inn’s bar will make your stay exceptional.

4. Stay in the Bahama Village for the Vibrant Colors and Caribbean Flair

Bahama Village
The colorful sign which welcomes visitors to the Bahama Village

The residential Bahama Village seduces with its radiant Caribbean architecture and laid-back vibe. 

After arriving in the area in the 19th century, the Bahamian settlers opened shops, bars, and restaurants in the area. Locals have always loved hanging up there. Even Hemingway has often visited and watched arm wrestling and boxing matches.

Nowadays, open-air restaurants line Petronia Street. Treat yourself to their mouthwatering seafood dishes and coconut-rich cocktails. Many will entertain you with live music sessions as well.

The charming area stretches for 12 blocks. If you enjoy vibrant colors and Caribbean flavors, book your accommodation in Bahama Village.

Our recommendations: The cozy apartment at The Galleria – Salvador’s Suite #4is located in a typical Caribbean house in the heart of Bahama Village, close to all of Key West’s attractions. You’ll have access to a kitchenette, a patio, and a small, refreshing swimming pool.

5. Stay at Casa Marina for the Perfect Beach Vacation

Southernmost Point
The Southernmost Point is probably the most famous photo op in Key West

An island vacation is (mostly) about the beach.

In Key West, the best beaches are in an area called Casa Marina. The tiny neighborhood boasts the best Key West beaches. These include:

  • Rest Beach: a white-sand stretch, great for sunbathing, picnicking, and gathering seashells.
  • Higgs Beach: a small sandy beach with clear waters, perfect for surfing, kayaking, and snorkeling.
  • Straw Hat Beach: the most secluded Key West beach, great for escaping the crowds.
  • Fort Zachary Taylor Historic State Park: the beach in the park is arguably the best Key West beach. We’ll leave finding out if that’s true to you.

One of the most surprising facts about Key West is that the sand on its beaches comes from the Bahamas.

In Casa Marina, you’ll also find the Southernmost Point of the Continental U.S.A. The buoy is the most famous photo spot in town.

If you’re looking for the perfect resort for your beach vacation, here are the hotels with the best beach in Key West.

Our recommendations: For the best beach experience in Key West, stay at one of the hotels, which offer private beach access. Adjacent to Higgs Beach, you’ll find Casa Marina. Another great beach resort is The Reach. Both offer private white-sand beaches and spectacular views over the Atlantic Ocean.

6. Stay at Smathers Beach for Sunbathing Under the Airplanes

Smathers Beach
Smathers Beach – the largest public beach in Key West

The only other “beach area” in Key West is around Smathers Beach.

It’s located next to the Key West Airport. Some might find the airplanes taking off over their heads bothersome, while others might think them fascinating. If you’re in the second group, you’ll love your stay at Smathers Beach.

The sand on the most popular and largest Key West beach also came from the Bahamas. Smathers Beach is perfect for volleyball, jet skiing, and windsurfing.

Our recommendations: Stay at Barbary Beach House Key West for the peaceful location just a few steps from the beach. You can take advantage of the free water activities, the large swimming pool, and the luxurious amenities.

7. Stay at Stock Island for the Budget-Friendly Family Accommodations

Stock Island
The bridge that connects Key West and Stock Island

If you prefer to stay a bit further from the partying crowds in Key West, then Stock Island is the best place for you.

The island is even smaller than the southernmost inhabited island of the Florida Keys. The establishments you’ll find here aren’t as crowded and pricy as the ones in the City of Key West.

Situated just 3 mi (4.8 km) from the Old Town, you can choose from several great, affordable resorts here.

Crossing one bridge is all it takes to get from Stock Island to Key West. If you’re traveling by car, this will only take a couple of minutes. And if you don’t have a vehicle at your disposal, you can ride the Key West bus for just $2.

Our recommendations: The fabulous Perry Hotel & Marina Key West seduces with luxury accommodations, two waterfront pools, three dockside restaurants, and a complimentary shuttle service to the Old Town. Plus, the staff can organize a private sailing tour for you.

Where Will You Stay in Key West Next?

Victorian Mansions in Key West
No more wondering where to stay in Key West – now you know the best places to stay in the southernmost U.S. city

There you have it – the 7 best areas to stay in Key West on your trip to the southernmost U.S. city.

Despite its compact size, the town offers a wide variety of accommodation options.

Sure, prices aren’t cheap, even in the off-season. However, the interesting designs, the luxurious amenities, and the great service make the experience worth your money.

So, regardless of whether you want to soak in history and culture, party the night away, or relax at the beach, you’ll find the right lodging for you.

And if you need inspiration on what to see and do during your visit, check out our Key West travel guide.

Now, we’d like to hear in the comments below:

Which area would you stay in next time you travel to Key West?

Where to Stay in Key West Pin 2
Where to Stay in Key West Pin 1
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Naddya

Naddya has been road tripping on four continents in altitudes from 0 to 4,655 m. She spent 12 years in Germany studying, working, and partying. In this time, she visited approximately 253 European cities by planes, trains, and automobiles. Her favorite activity is to get lost and then find her way again. Fun fact: Naddya has a love for islands and a hatred for tan-lines.

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