Where to Stay in Key West, Florida First Time: 11 Best Areas

The best areas to stay in Key West for first-timers are Duval Street, Historic Seaport, Smathers Beach & New Town, Bahama Village, Mallory Square. These are popular neighborhoods that offer a wide variety of tourist attractions and amenities.

In today’s post, I’ll be going over where to stay in Key West for tourists, nightlife, shopping, and family.

Key West is famous for its sunset, the locals and tourists celebrate the sunset in Mallory Square every evening. It’s also known for lively nightlife, beautiful beaches, historic sites with its pastel, conch-style architecture. Key West is also home to Ernest Hemingway and many other writers.

Old Town is the best place to stay in Key West for first-timers because it is a large area with the biggest collection of attractions and hotels. However, those wanting to stay near the airport will be better off in New Town. This is also a great choice for those on a budget as well.

Those visiting for New Year’s Eve will want to consider the historic seaport. With beautiful views of the fireworks over the water and a bar that hosts the most iconic event of the night, it is the destination that gives you the most complete experience.

The southernmost point in the continental United States, Key West is perfect to enjoy a secluded break amongst the palm trees, some 100 miles south of where Key Largo joins the mainland, no matter what you’re looking for. At its Southernmost Buoy, Key West is just 90 miles to Havana, Cuba. It’s closer to Cuba than Miami.

💖 Best Area for First-Timers:Old Town
💎 Best luxury hotel:Hyatt Centric Key West Resort & Spa
🏨 Best mid-range hotel:Simonton Court Historic Inn & Cottages 
💰 Best budget hotel:Douglas House 

Where to stay in Key West? 11 Best areas to stay in Key West for tourists

1. Old Town, where to stay in Key West for first-timers

Old Town (Key West Historic District), where to stay for first time visitors

Old Town is the best area to stay in Key West for first time tourist because it is where the most attractions, hotels, and restaurants are located. Key West Historic District is the town center and the history and cultural hub of the island. Old Town is a large district in the far west of Key West containing a number of sub-districts that we will look at further down such as Duval Street, Mallory Square.

In total, the Key West Historic District contains almost 2500 historic buildings and structures, many of which are listed on the National Register Of Historic Places. This makes it ideal for anyone wanting to learn about the history of the city during your stay in Key West.

For starters, you have the Audubon House & Tropical Garden Museum. Dedicated to the life and works of famed ornithologist James Audubon, a collection of 28 first editions of his work are stored within the house, along with a fabulous collection of antique furnishings. 

Combined with its beautiful, historic architecture and the stunning gardens where he discovered and drew 18 of the birds from his “Birds Of America”, it is a great destination for fans of his work, nature, and wonderful architecture alike.

You have the Key West Shipwreck Museum, which contains artifacts, films, and live performances, telling the story of over 400 years of shipwrecks and salvage operations in the Florida Keys.

The Mel Fisher Maritime Museum is another similar attraction, featuring artifacts from famous 17th-century shipwrecks, including the Henrietta Marie, Nuestra Senora De Atocha, Santa Margarita. It also includes an exhibition on the freeing of slaves in the area in the 1860s.

In terms of historic buildings, you have locations like the Basilica Of St. Mary Star Of The Sea, one of the oldest Catholic churches in the state of Florida. There is also the Oldest House Museum & Gardens, which contains facts and exhibits about Key West, housed inside its oldest structure.

Other historic buildings include The Armory, a 19th-century military training house, The Fogarty Mansion, Richard Beacon House, Dr. Joseph Y. Porter House, and the Key West Heritage House & Robert Frost Cottage.

There is even the Key West Cemetery which, with more than 100,000 people interned here, features more than triple the current population of Key West, which stands at around 30,000.

For those who like history but aren’t overly interested in sightseeing, why not stay at a historic hotel or spend some time in one of the historic bars in the area, such as Sloppy Joe’s (a favorite American Bar of novelist Ernest Hemingway) or Captain Tony’s Saloon

These bars have stood in their location for decades and have been frequented by all manner of famous visitors, from actors to Presidents. That makes them a great place to kick back and relax with a cold drink while taking in some history and culture.

With all of this and more, it is no wonder Old Town is one of the most popular neighborhoods in Key West. You can easily find beds and breakfasts that are converted from many buildings that date back 1800s.

Stay In Key West Historic District If you are interested in the history of Key West; you want to stay in close proximity to the majority of the attractions on the island; you want to stay in a historic Key West hotel.

Best places to stay in Old Town:

💎 luxury ($$$): Hyatt Centric Key West Resort & Spa This waterfront resort is located in the heart of Key West, within walking distance from the nightlife and restaurants of Duval Street. it offers cozy rooms with a private balcony, free WiFi, an on-site spa, a fitness center, and 2 on-site restaurants Shor American Seafood Grill and Blue Mojito Pool Bar and Grill.

🏨 mid-range ($$): Simonton Court Historic Inn & Cottages this Florida adult-only inn is located within a short drive from Duval Street, the Ernest Hemingway Home and Museum, the Southernmost Point of the continental United States of America, Mallory Square, and Smathers Beach. It has a continental breakfast, free WiFi, rooms with a TV, a telephone, and a refrigerator, and 4 on-site outdoor pools.

💰 budget ($): Douglas House This inn is located near Key West Lighthouse and Keeper’s Quarters Museum. You are close to South Beach, Fort Zachary Taylor Beach, Higgs Beach, Rest Beach, Simonton Street Beach, and Smathers Beach.


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2. Duval Street, where to stay in Key West for nightlife

Located in the heart of Old Town, Duval Street is the main drag in the city. It’s a 1.25-mile north-south street that connects the Gulf Of Mexico to the Atlantic Ocean. It’s is packed with activity, live music, bicyclists, pedicabs.

At the south end near the Southernmost Point of the Continental U.S.A. stands the oversized buoy that attracts many people to take photos.

The area is filled with mansions featuring wonderful Bahamian and Spanish takes on Victorian ‘Conch’ architecture, making it a unique destination for anyone interested in architecture and design.

In a similar vein, numerous art galleries also fill the surrounding streets, giving you the opportunity to take in some of the local styles.

A plethora of shops and boutiques offer all manner of products, providing visitors with hours of options to stroll and browse through. Then, when you’re all shopped out, a collection of bodegas and inns give you a place to unwind.

And there are more than 100 bars in 15 blocks, these bars open till early morning. it’s a great place if you are looking for parties and nightlife!

Being located so close to Cuba, there are plenty of establishments where you can enjoy that culture as well. Cafes serve Café Cubano, a traditional type of Cuban coffee. Why not unwind sitting in the sun sipping a cup and puffing on a Cuban cigar.

When you want a drink with a little more excitement, the bars to the north end of Duval Street offer a vibrant and active atmosphere. With an abundance of cruise ships docking nearby, resorts like the legendary Margaritaville provide fun and activities especially aimed at tourists hoping to party.

This energy, culture, and history have led to Duval Street developing a reputation amongst the rich and famous through the years. People like Harry S. Truman and Ernest Hemmingway are just a couple of the famous names who will have drank in the same bars as you if you choose to stay here.

Duval Street also hosts events and festivals during the year including the Conch Republic Days, Songwriters Festival, Poker Run, Hemingway Days, and Fantasy Fest.

Families with children will want to visit the Key West Butterfly and Nature Conservatory with more than 50 species of butterflies.

Stay In Duval Street If you want to stay in the downtown area of Key West; you want to stay in one of the best hotels in Key West; you want a range of amenities and attractions just a short walk away.

Best places to stay in Duval Street:

Duval Gardens This adult-only bed and breakfast is within easy walking distance from the Butterfly and Nature Conservatory. This inn offers an outdoor heated pool, continental buffet breakfast, and free WiFi.

Santa Maria Suites Resort This resort is just 1 block from the Atlantic Ocean and Duval Street, close to the Clinton Market Square shopping area, Ernest Hemingway House, and Fort Zachery Taylor Historic State Park. It offers suites with a full kitchen and flat-screen cable TVs, 2 outdoor heated pools, and free wifi.

Avalon Bed and Breakfast This bed and breakfast is on the National Register and the Cuban Heritage trail, 700 m from Ernest Hemingway’s House and the South Beach,  the Key West Butterfly Conservatory, the Southernmost Point, 350 m from Barefoot Billy’s Watersports as well as bars, cafes, and fine dining restaurants like Pisces by Café des Artistes, and 8km from Key West International Airport.


3. Mallory Square, where to stay in Key West for sunset

Mallory Square, where to stay in Key West for sunset

Our next area of Mallory Square is again located within Old Town, this time on the coast at the northwest point of Key West. Mallory Square is a bustling plaza filled with restaurants, shops, bars, attractions, and views, all just a short walk from one another.

Mallory Square is best known as the home of the Sunset Celebration, a nightly festival that is known as one of the primary tourist attractions on the island. With its western location and unobstructed views, it offers some of the best sunset’s you will find anywhere in Key West.

Each night hundreds of tourists flock to the square to watch the sunset over the Gulf Of Mexico. Countless arts and crafts exhibitors, food carts, and street performers are present from 2 hours before sunset, helping to create a true carnival atmosphere.

Cruise ships are even required to leave the dock in front of the square from when the vendors arrive until after the sun has set. This ensures everyone can have a fabulous time, eating, drinking, being entertained, buying local products, and enjoying one of the most beautiful, natural scenes on Earth.

The Sunset Celebration isn’t the only reason to stay in Mallory Square though. For starters, you also have the Key West Historic Memorial Sculpture Garden. With beautiful bronze busts of 39 historic figures deemed important to the development of Key West, it is ideal for art and history fans alike.

Then you also have the Key West Aquarium. One of the oldest aquariums in Florida, it is home to alligators, jellyfish, sharks, turtles, and Atlantic Shore Fish. With touch tanks and numerous exhibits, it is a great place to visit for anyone interested in the marine life of the area.

Ripley’s Believe It or Not! Odditorium is another highlight that is worth visiting for all ages.

If you interested in history, there are couples of museums to explore including the Key West Shipwreck Museum, Key West Museum of Art & History at the Custom House, and Mel Fisher Maritime Museum.

Being located in the busiest part of Key West also means you will have plenty of options in the surrounding areas. Therefore, you are almost guaranteed to find a Key West hotel that perfectly complements your trip and ensures you have a vacation to remember.

Stay In Mallory Square If you want to witness and be a part of the Sunset Celebration; you want to visit the Key West Aquarium or Memorial Sculpture Garden; you want easy access to some of Key West’s best hotels, shops, bars, and restaurants.

Best places to stay in Key West Mallory Square:


4. Historic Seaport, where to stay in Key West for ferry trips

Historic Seaport, where to stay in Key West for ferry trips

Located immediately to the east of Mallory Square and north of Duval Street, Key West Historic Seaport is the busiest part of the entire city. Multiple marinas are full of stunning yachts and vessels, while the Key West Express ferry service takes passengers on voyages across the Gulf Of Mexico.

You also have a collection of companies offering tours on fishing boats or private hires, allowing you to get out and spend some time on the water. There’s even a water sports company, where you can take part in activities such as boat rides, windsurfing, parasailing, snorkeling, and even catamaran cruises.

Around the historic seaport, numerous bars, restaurants, and coffee shops provide you with places to enjoy a drink or meal, while watching the boats bob up and down on the waves.

Perhaps the most famous is the Schooner Wharf Bar, which is known for its live music and New Year’s Eve festivities.

Historic Seaport offers beautiful sunset views around the port. You can enjoy drinks and meals while watching the sunset at Bistro 245 and El Meson De Pepe’s Restaurant & Bar.

With some of the most scenic views in Key West and convenient access to the most popular areas, the historic seaport is a great choice for anyone who wants a relaxing break, where they have access to everything the island has to offer.

However, with so much going on, it is an area that gets remarkably busy. This means you may need to book in advance and be aware of issues like limited parking and large crowds.

Stay In Historic Seaport If you want to go on a cruise; you aren’t worried about limited parking or large crowds; you are a fan of water sports; you find eating and drinking while watching the boats in the marina relaxing.

Best places to stay in Historic Seaport:


5. Bahama Village, good neighborhood for food and restaurants

Bahama Village, good neighborhood for food and restaurants

Located in the south of Old Town, Bahama Village is named after the original population of the area, which was predominantly from the Bahamas. This allows the area to offer a slightly different feel and culture than the rest of Key West.

This can be seen everywhere from the abundant shops, restaurants, and hotels to the local people that still inhabit the area. With the southern section of Duval Street running through Bahama Village, it is also incredibly well connected to the rest of the city center.

Perhaps the most famous attraction in the area is the Key West Light House Museum. Constructed in 1848 after hurricanes destroyed the first two lighthouses in Key West, it stands 50 feet tall and is one of the most iconic structures on the island.

Directly opposite the lighthouse, you will also find the Ernest Hemingway Home. Constructed in French Colonial Style just 3 years after the completion of the lighthouse, it has become the most visited attraction on the island.

The site where he wrote some of his most famous works, it has been fully restored and designated a National Historic Landmark. It now operates as a museum to his work and still features a population of polydactyl cats like those he owned, with many believing they’re descended from his actual pets.

The other well-known attraction in Bahama Village is the Southernmost Point Of The Continental U.S. While the southernmost point is actually in the neighboring district, this is where you will find the monument, which is a popular photo opportunity for tourists in the area.

Bahama Village is also home to Fort Zachary Taylor, where you can learn more about the important roles of the fort in the Civil War and Spanish-American War. The park also boasts Key West’s favorite beach, Fort Zachary Taylor Historic State Park Beach, offering opportunities for picnicking, swimming, snorkeling, and fishing.

Accommodations in Bahama Village are cheaper than Old Town with B&B with Caribbean House.

Stay In Bahama Village If you want to stay in an area with a unique culture and Caribbean charm; you want easy access to the rest of the city center.

Best hotels in Key West Bahama Village:


6. Casa Marina, luxury area with private beach

Casa Marina, luxury area with private beach

The Casa Marina subdistrict is located on the southern side of the island, immediately to the southwest of Bahama Village. It is named after the luxury resort in the neighborhood that was founded by Henry Flagler in the late 19th century.

The highlight attractions in Casa Marina are Southernmost Point, Higgs Beach with a beautiful sunrise, and African Refugee Cemetery.

The area is known for its private beach and outdoor swimming pools. Often considered somewhat of a playground for the rich and famous, it is a fabulous choice for those who want a beach vacation with a stylish atmosphere and aren’t worried about spending big to pay for it.

At either end of the beach, beautiful piers jut out into the ocean. This allows you to stroll along, enjoying serene views while surrounded by nothing but water.

Attractions like a water sports company provide rentals for those looking to hit the waves and have some fun. Meanwhile, a sand artist creating sculptures to request on the beach offers a slightly more relaxing activity for those seeking a slower pace.

Then, no matter how you choose to spend your days, a great choice of bars and restaurants allows everyone to kick back and relax with some fine food and drink of an evening.

When you combine that with the shops and other facilities that are within close proximity, Casa Marina becomes one of the best spots on the island for those seeking a truly relaxing vacation.

Stay In Casa Marina If you aren’t worried about money; you want to relax on a private beach; you are interested in water sports or sand sculptures; you want a good choice of bars and restaurants.


7. Truman Annex, quiet residential area, good for family

The final Old Town subdistrict we will look at, the Truman Annex is located on the far west of the island. A neighborhood and military installation, it is named after former U.S President Harry Truman, as it is the location of his winter home.

The Harry S. Truman Little White House where he stayed has now been converted into a museum that is one of the main attractions of the area. It features artifacts and information about his life, located in rooms still decorated how they would have appeared during his time there.

Beyond the museum itself, the other main draw to the area is the Fort Zachary Taylor Historic State Park. With nature trails and a pre-Civil War fortress, it is a great place to get out and explore the history and landscape of Key West first-hand.

Not only that, but the park also has the best beach near the city center. With beautiful stretches of sand, water sports rentals, and unimpeded views across the Gulf to Cuba and Mexico, it is equally ideal whether you want to relax and enjoy the scenery or let loose and go wild on the waves. 

This is also a family-friendly area because it’s safe, quiet, and close to attractions such as Fort Zachary Taylor State Park, Truman Waterfront, Duval Street, and Downtown.

Stay In Truman Annex If you want to visit both a beach and the city center; you are interested in the history of President Harry S. Truman; you want to explore nature trails and historic sites in a state park.


8. New Town, where to stay in Key West on budget

New Town consists of almost everything on the main island of Key West to the east of Old Town. Unlike its neighbor, New Town is a much more residential area, with very few attractions designed specifically for tourists.

That said, it is still a great destination for anyone who prioritizes enjoying the natural beauty of their surroundings, as opposed to being overwhelmed by other tourists the entire time.

A great selection of restaurants and shops caters primarily to the locals, allowing you to sample some of the more traditional cuisines of the area. Without such a tourist reputation, you will also be able to do so for significantly less than you would find in the island’s hot spots.

While the more famous Key West hotels are mostly located to the west of the island, there are still a good range to be found here too. That means you shouldn’t have trouble finding a hotel, no matter what your budget or taste may be.

One of the main reasons many will choose to stay in New Town though is because it is the location of Key West’s main airport. This makes it ideal for anyone wanting to remain close so they don’t miss their flight, have to drag their luggage all over town, or for any other reason they may have.

Stay In New Town If you are traveling on a budget; you prefer a quieter, more residential area; you want to stay near to the Key West International Airport; you don’t need to be near the city center.

Best places to stay in Key West New Town:

9. Smathers Beach, where to stay in Key West with family

Located on the south side of the island, Smathers Beach is the largest public beach in Key West. 2 miles of beautiful golden sand meets crystal clear turquoise waters and is backed by rows of palm trees, creating a scene straight off of a postcard. 

This scenic appearance has helped Smathers Beach become recognized as the best beach anywhere in the Florida Keys. As a result, the beach is equally popular with locals and tourists alike, who swarm to Smathers to make the most of the beautiful weather of Key West. 

While this can lead to large crowds forming, its sheer size still means you are likely to find a spot perfectly suited to your own personal needs. For example, some parts feature water sports, such as jet skis, so the thrill-seekers can get out on the ocean, ride the waves and get their blood pumping. 

Then there are sections that feature sports like volleyball. Those who love some good-spirited competition will be able to get their fill, whether they want to participate themselves or simply spectate on the events.

There are even plenty of sections that are simply just a little quieter and less populated. This makes them ideal for those who just want to laze on the sand, topping up their tan, and perhaps go for the occasional dip in the ocean.

Likewise, this also makes it great for families with small children. You can give them the freedom to play in the sand and help them learn to swim, without worrying about them making too much noise as you might on a smaller beach.

When you are done after a long day in the sun, there are also showers available for the public to use. This means you can rinse off and spend an early evening at one of the bars or restaurants located near the beach to complete your day before heading back to your hotel.

Stay In Smathers Beach If you are a fan of water sports; you like long sandy beaches; you are traveling as a family or with small children; you don’t need to be near the city center.


10. Sunset Key, where to stay in Key West for luxury

Sunset Key, where to stay in Key West for luxury

Sunset Key is a small island, located 500 yards off the north-western coast of the main island. Originally known as Tank Island, it was built in 1965 during the Cold War, both to create passages for submarines and other large vessels, as well as to be used as a fuel tank depot.

After eventually being sold in 1986 it continued to be developed and change hands for almost a decade until it was renamed Sunset Key in 1994. It is now owned by Tom Walsh, who also owns the Margaritaville Key West Resort & Marina.

It has since become known as one of the most exclusive parts of the entire archipelago. The key consists of a collection of 69 family homes and vacant lots, each of which is valued at more than 1.5 million dollars.

A small fleet of 4 ferry boats known as Island Time, Lil’ Princess, Serenity, and Sierra are the only way to reach the island, all of which run between it and the Margaritaville Marina.

A single resort is present on the island, the Westin Key West Resort. With a private beach, a small collection of waterfront cottages, a spa, and a restaurant, it is one of the most sought-after Key West accommodations, as a booking there is the only way to visit the island for non-residents.

With only a handful of other guests staying at the hotel and a collection of residents who value their privacy, Sunset Key is the perfect location for a truly secluded getaway, where you can enjoy your own slice of tropical paradise, without worrying about prying eyes all the time.

Stay In Sunset Key If you want to stay in one of the most exclusive Key West hotels; you aren’t worried about money; you are happy to book well in advance; you want a break in a secluded, tropical paradise.

11. Stock Island, a residential area in Key West

Our final destination of Stock Island is technically located outside the limits of Key West, instead of being located in the eastern part of the region. Unlike Key West, Stock Island is a primarily residential area, with a larger population that remains on the island year-round.

The island is particularly known for its artistic community. Numerous enclaves and establishments exist in the area, such as Stock Yard Studios, The Art Shack, Washed Up Studios, Art At The Perry Hotel, Studios At Stock Island Marina Village, and Studios At Safe Harbor.

This makes it a great option for aspiring artists, as well as those who simply appreciate works of art. Beyond art, sailing and golf are the other dominant pastimes here. 

A collection of 10 marinas and boatyards ensure you will always find somewhere to store your vessel or rent one for a day. There are even hotels like Perry Hotel Key West that include their own marina, so you never need to be too far from your ship.

Meanwhile, the Key West Golf Club takes up nearly a quarter of the west side of the island. Featuring a beautiful golf course, it gives you the perfect opportunity to get out on the links and play a few rounds during your visit.

There aren’t a great number of tourist attractions on Stock Island, but the Key West Tropical Forest & Botanical Garden is a nice stop for nature lovers. A collection of trees, shrubs, and palms demonstrate how the local plant life differs to that elsewhere in the united states.

If you happen to be in the area during December, there is also the I Love Stock Island Festival. Running for 3 days, a lighted boat parade, tours of the island, culinary contests, and promotion for the arts and businesses of the island create a wonderful atmosphere for all to enjoy.

Numerous restaurants and food trucks serve all types of cuisine, from fine dining to street food. This makes it a perfect choice for foodies who want to try as many things as they can during their stay. 

Hotels aren’t overly abundant in the area, but there is still a nice selection to choose from. That said, it is worth booking in advance to avoid your chosen hotel selling out and leaving you disappointed.

Stay In Stock Island If you want to go to the I Love Shutter Island Festival; you are interested in art, golf, or sailing; you want to visit the botanical garden; you prefer a more residential area and are happy to book early.


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Overall, I recommend Old Town as the best area to stay in Key West due to its prime location. If you stay here, you will be located in the heart of action, within walking distance to tourist attractions, as well as, shopping, dining, and nightlife. Old town also offer a widest range of accommodation options for all budget travelers.

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