Ultimate Guide to Best Key West Beaches, Resorts (and More)

Here's the inside scoop on the best Key West beaches, resorts, restaurants and activities.

Key West is at the very tip of a string of islands south of the Florida coast. A mere four-hour drive from Miami, this is where Floridians vacation.

You can fly directly into Key West, but if you can swing a short road trip, driving through the Florida Keys is an experience that’s very much worth it. At the end of the road, you’ll find a town famous for its diving opportunities, raucous parties, colorful mid-century houses and an abundance of sunny days.

Ready to enjoy the place Ernest Hemingway once called home? Here’s an ultimate guide to Key West’s best beaches, resorts, restaurants and more.

Best Key West Beaches

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Outside of Orlando, the beach is the reason most people come to Florida.

As you’d expect from a group of islands, there are plenty of great Florida Keys beaches — you just have to make sure that you manage your expectations. Soft-sand beaches are the exception, with most beaches being narrow and rocky. This is because the Keys are surrounded by the third-largest coral reef system in the world, an asset that prevents erosion.

Even without soft sand, heading to the beach is the best thing to do in the Florida Keys and in Key West specifically. If you love the water, make sure you spend time in at least one (hopefully all five) of these amazing Key West beaches.

1. Smathers Beach

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Remember what we said about sandy beaches? Smathers Beach is the happy exception to this (though the sand is, of course, imported).

The largest and most popular beach in Key West, Smathers is located only three minutes away from the airport, making it a popular first stop for vacationers. Stores and restaurants line up near the shore, so you can enjoy fresh fried fish after a good swim or get the sunblock you inevitably forgot to pack.

Plenty of shops also rent water sports equipment for kayaking, snorkeling, wind sailing and other activities.

2. Fort Zackary Taylor Beach

Fort Zachary Taylor State Park Beach Key West Florida

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Not your typical beach experience, Fort Zachary Taylor State Park is a protected natural and historic area. The beach is the main attraction with a natural shoreline of harsh coral that makes it a favorite with locals who prefer its authenticity.

The reefs near the shore provide ample opportunities for an underwater safari that doesn’t require anything except goggles. But once you’re done playing in the water, make some time to go on a tour of Fort Zach (as it’s known colloquially) or walk through one of the two short trails in the park.

3. Higgs Beach

Key west florida beach Clearence S Higgs

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If you want an alternative to Smathers Beach that’s a bit quieter, head to nearby Higgs Beach.

Higgs also boasts imported sand as well as numerous palm trees that make for perfect pictures and plenty of amenities. Renting beach chairs and umbrellas is as easy as Key lime pie, and there are dog-friendly areas nearby. A long pier makes it possible to get great views of the water without getting wet.

This beach is also an important historical site, as it was the final resting site of hundreds of Africans who were rescued from illegal slave ships. You can visit the memorial and pay your respects.

4. South Beach

Old pier at South Beach, Key West, Florida Keys

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No, not that South Beach, the South Beach — the actual southernmost beach in the entire United States.

South Beach is decidedly about the Florida Keys lifestyle, with a laid-back vibe and limited facilities. Don’t worry, though, there are still shacks selling refreshing drinks that you can enjoy as you sunbathe.

With shallow, calm waters (again, let’s thank the reefs!), this is one of the most family-friendly beaches. As a bonus, the Southernmost Point is nearby, so you can kill two pelicans with one stone.

5. Bahia Honda State Park

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Though Bahia Honda is actually about an hour away from Key West, we simply had to include it, given that it is continually declared the best beach in the Florida Keys.

The state park is an idyllic and secluded sanctuary where you’ll truly get away from the noise of civilization. Here, you’ll find one of the few natural white-sand beaches in the Keys, a rarity that is made even more special by the light blue water that encircles it.

Despite the distance, this is one of the best Key West campgrounds, for those inclined for adventure. It’s also a state park that you can arrive at by boat.

Best Key West Resorts

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Although land is limited in Key West, the city has an impressive array of hotels and resorts that cater to different types of travelers.

Whether you’re looking for easy access to the beach, a space away from it all or to be at the heart of the party, these are the best Key West resorts.

Best Overall Key West Resort: Casa Marina

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Originally built in 1888 and turned into a resort in 1921, Casa Marina is listed on the National Register of Historic Places.

Besides getting to experience a piece of Key West history, you’ll get the amenities that can be expected from a Hilton Curio Collection resort: a beach concierge, a luxurious in-house spa and over 1,000 feet of sand from which you can enjoy the sea.

Getting up early to watch the spectacular sunrise at least once is highly recommended.

Stay at Casa Marina Resort

Best Key West Resort for Couples: The Gardens Hotel

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Couples usually go for a beachside hotel for an amorous escapade. But we actually think the most romantic hotel is the Gardens Hotel.

Although it doesn’t have access to the beach, it does provide a secluded setting inside a lush tropical garden. Stay at a cottage, and enjoy a private entrance and a veranda where you can sip wine or refreshing iced tea. Best of all, this is an adults-only hotel, so you won’t have to worry about children and noise.

Walking to the beach will take you through Duval Street and some Key West landmarks like Hemingway’s house. For a truly special night, book a private serenade dinner in the courtyard.

Stay at the Gardens Hotel

Best Key West Resort for Families: Sunset Key Cottages

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When traveling with kids, convenience is what matters the most. Sometimes, this is impossible to get in a small hotel room, so booking a seafront cottage on a private island is the way to go.

Sunset Key is mostly residential, but vacationers have access to the cottages. Perks include not having to worry about loud parties that’ll keep the kids up, a private beach, a pool, tennis courts and a kitchen, in case your child is a picky eater.

The resort offers a boat shuttle service that will easily and quickly connect you to the “mainland.”

Stay at Sunset Key Cottages

Best Key West Resort for Friend Groups: Ocean Key Resort

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If you’re traveling with friends, however, you’ll want to be right in the middle of it all. Ocean Key Resort is located in Zero Duval Street, at the heart of the city. You’ll be perfectly positioned to step out and into the best parties and nightlife in Key West.

Each room comes with a balcony that boasts a view of either Duval Street or the Gulf of Mexico. Resident artists, writers and performers bring life right into the property, which is part of the Curator Hotels and Resorts Collection. It also boasts the Sunset Pier, a beloved spot where live music and food complement the spectacular sunsets.

Stay at Ocean Key Resort

Best Key West Resort for Staycations: The Marker Resort

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With remote work becoming increasingly common, some people are choosing to spend a couple of weeks enjoying the magic of Key West.

For the best combination of business and leisure, nothing beats the Marker Key West Harbor Resort. For one, most rooms have a desk you can work from and spacious suites that make for a comfortable, prolonged stay. It’s also near enough Duval Street, Mallory Square and the seaport to provide easy access to fun activities but far enough to keep you away from the noise when you need to concentrate.

When you’re not working, wind down with poolside yoga, or enjoy Starboard, the resort’s in-house restaurant famed for its delectable seafood. That or relax in the private soaking tub in your room.

Stay at the Marker Key West Harbor Resort

Best Things to Do in Key West

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Key West is here to prove that when it comes to activities, size definitely doesn’t matter. Of course, a lot of what you’ll be doing during a trip here will be near, on or in the water — we did say the beach was the best thing to do in the Keys.

But there are plenty of attractions and things to do outside the water as well. Some of the famous ones include visiting the Southernmost Point and riding the Conch Train through Old Key West. And while these are worth it, there are better ways to spend your day.

To maximize your time in the city, here are the five best things to do in Key West that you can’t miss.

1. Spend a Day at Dry Tortugas National Park

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If you’ve never heard of this Florida gem, you’re not alone. Most people are completely unaware of this beautiful national park, which is almost entirely underwater.

The only way to get here is by a ferry that will take you to Fort Jefferson, a Civil War fortress that constitutes most of the overwater part of the park. You’ll be one of a little over 79,000 people who visit Dry Tortugas, which is the eighth least visited national park in the U.S.

Besides the fort, the park has a beautiful secluded beach and provides some of the best Key West snorkeling opportunities — after all, how often do you get to snorkel around a fort?

2. Visit Hemingway’s House

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One of the unmissable landmarks in Key West is the Ernest Hemingway Home and Museum.

The famed author lived in Key West from 1928 to 1939, leaving his mark on the town. This house museum was originally built in 1851 and served as a home for Hemingway and his second wife, Pauline Pfeiffer. (Ironically, he also met his third wife, Martha Gellhorn, in Key West.)

Works like “Green Hills of Africa,” “The Snows of Kilimanjaro” and “To Have and Have Not” were breathed into life in this house, which continues to attract visitors with Hemingway paraphernalia. Another great attraction is the six-toed cats that roam the property, all descendants of Hemingway’s six-toed pet, Snow White.

3. Walk Through Duval Street

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The beating heart of Key West, you couldn’t avoid Duval Street even if you tried. Dotted with historic houses that range from Spanish-influenced Victorian mansions to Bahamian-style cottages, the street is where you’ll find most of the town’s entertainment.

While some of the beautiful and colorful historic houses are still residential, the majority now house boutique shops, restaurants, bars, nightclubs, bed and breakfasts, and art galleries. You’ll probably spend a lot of time in this street and never get bored of it.

4. Attend a Sunset Party at Mallory Square

Sunset party at Mallory Square, Key West

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If you walk Duval Street all the way to the Gulf of Mexico, you’ll end up in Mallory Square.

While the square is graced with numerous restaurants, bars and shops, what really draws people here are the sunsets. Every single evening, the square fills with hopeful crowds and a carnivalesque air, as street performers sing, juggle and do magic until the sun goes down.

5. Get Close to Nature at the Key West Butterfly and Nature Conservatory

Tiger Longwing Butterfly at the butterfly conservatory, Key West

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Take a break from the crowds and the beach at the Key West Butterfly and Nature Conservatory. The sanctuary protects around 60 species of butterflies, which often swirl around you, making you feel like you’re in a Disney movie.

Other species like beautiful pink flamingos also reside here. The conservatory is always a hit with kids, so it’s the perfect Key West family attraction out of the water.

Best Restaurants in Key West

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A mix of American, Cuban and Caribbean cuisines makes food in Key West so good that people come down here just to eat as much of it as possible.

You can’t leave without eating Key lime pie at least once — once a day, is what we say — preferably from the famous Key Lime Pie Co.

But for fuller meals, you’ll have your pick of choices in these five best restaurants in Key West.

1. Blue Heaven

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After you’ve tried Key Lime Pie Co., come to Blue Heaven and order a slice of their Mile-High pie, with a generous cream filling that makes it rise up toward the sky.

As for food, the choices are quite cosmopolitan, with fresh seafood dishes, jerk chicken, curry soups and avocado omelets. The atmosphere is laid back in a way that feels homey, with lots of vegetation surrounding the blue building, and cats and roosters casually passing through.

2. The Lobster Shack Key West

The Lobster Shack Key West / Facebook

If you’re serious about your seafood and want to try some of the best lobster in Florida, there’s no better place than the Lobster Shack.

You can come right after an obligatory stop at the Southernmost Point and enjoy more variations of lobster than you could’ve ever imagined. The fresh lobster salad is always a hit, with one type that includes Key lime juice.

3. Louies’ Backyard

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Set in a beautifully restored Victorian home, Louies’ Backyard is a gourmet restaurant that still manages to feel welcoming rather than pompous. The building is listed on the National Register of Historic Places, so you know you’ll have a beautiful backdrop to your meal. Other things you’ll definitely enjoy are the views of the water and the shade from the trees on the patio.

The menu changes seasonally, but you can expect mouthwatering items like seared duck foie gras with bacon and honey spiced apple butter or pesto-rubbed sword fish.

4. Pepe’s Cafe

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If you’re more into casual restaurants that are reasonably priced and generous in their portions, Pepe’s Cafe won’t fail you.

With an old-school diner vibe and philosophy, Pepe’s is the kind of place you can go to straight after the beach. The baked oysters are absolutely delicious, but if you want something more diner-y, the sandwiches are popular as well.

5. Little Pearl

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If on the other hand you want an upscale dining experience that still feels coastal, Little Pearl is the place to go. Located in Old Town, the restaurant only offers a four-course Chef’s Menu that usually focuses on seafood.

Yes, the options are limited, but we assure you that you can trust the chef to bring out five-star dishes every single time.

Best Key West Bars

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What’s a Key West vacation without a little bar hopping?

For a town its size, Key West has a surprisingly happening nightlife, capitalizing on the promise of a beach town party. There are too many bars to count, some are historical and very much worth a visit, while others are the generic places you can find anywhere in the country.

Avoid the meh places, and go to these best Key West bars that will definitely wow you.

1. The Bull & Whistle Bar

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Affectionately known as The Bull, this historic establishment claims to be the last of the open-air bars that once defined Duval Street.

But just because it’s historic doesn’t mean it’s quaint. This is one of the most raucous places you’ll find in Key West, with three floors that offer three different experiences. Stay on the first floor for live music and an old-timey bar feel. If a sports bar is more your thing, head to the second floor, where you’ll find pool tables and other bar games.

For the bold at heart, the third floor is a rooftop bar with beautiful views of the town — just be advised that it’s clothing optional, and people very often go for that option.

2. Sloppy Joe’s Bar

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This is one of two restaurants that battle for the title of being the original Sloppy Joe’s — the one where Hemingway and a cohort that included John Dos Pasos, Waldo Pierce and Henry Strater often met for drinks and shenanigans.

But whether this was the original or not, the bar is still historic and serves a mean Sloppy Joe sandwich that you have to try before going back home. There’s also live music every day of the week from noon to 2 a.m., so you’ll always have a show with your drink or dinner.

3. Captain Tony’s Saloon

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The other bar claiming to be the original Sloppy Joe’s is Captain Tony’s Saloon. Besides Hemingway, the bar claims to have been a favorite spot for the likes of Truman Capote and Tennessee Williams.

But whether its ties to “Papa” are real or not, the truth is that Captain Tony’s has a very interesting history, as it once served as the town’s gallows and, later, as a morgue. You can still see real tombstones popping up randomly from the floor. If you look up, you’ll be met with thousands of dollar bills hanging from every inch of the ceiling. There’s also a large tree in the middle of the bar that bursts through the ceiling.

This is definitely a bar you won’t find anywhere else.

4. Bourbon St. Pub

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Key West is known for being one of the most queer-friendly destinations in the entire U.S. And there’s no gay bar more exciting than the New Orleans-themed Bourbon St. Pub.

The bar has weekly drag shows, theme nights where people are welcome to dress up and an outdoor pool that makes for wild pool parties.

If you happen to spend New Year’s in Key West, this is the place to go. Skip watching the ball drop on TV and head out to see the bar’s giant red slipper drop.

5. Hogfish Bar & Grill

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Touting itself as a look into what the Florida Keys used to be, we love Hogfish Bar & Grill for its laid-back, casual atmosphere.

Their claim is not empty, the bar really has managed to keep that grouchy feel that once made the Keys a perfect place to hide from the world. If you like fresh seafood, you’ll love it here, since you can actually see the fish being brought in by boat right before you feast on it.

The best part is that the Hogfish is not on Duval Street, so you’ll find many more locals than tourists here. Oh, and the drinks are good and strong.