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Where to Stay in Key West: 6 Best Areas & Neighborhoods

Where to Stay in Key West: 6 Best Areas & Neighborhoods

Colorful, quirky, and stocked full of key lime everything, Key West is as close to the Caribbean as you can get without a passport if you live in the United States. If you’re planning a vacation to the Florida Keys, you’ll want to read below to see where to stay in Key West.

The small island at the end of the Florida Keys was discovered by Ponce de Leon around about 1513. It gained prominence (or would it be notoriety?) when it declared secession from the rest of the U.S. in 1982 and took on the aptly-chosen moniker of Conch Republic.

This act of secession was in protest to a border patrol by the U.S. Government, which caused a 17-mile backup. Who knows what they were looking for (drugs, guns, aliens, Elvis …. ?).

This unprecedented roadblock (within the actual United States) really made folks mad, as travelers apparently started canceling reservations and plans to visit the Florida Keys and Key West. Hence, the Conch Republic was born as a sovereign state of mind. But, yes, it’s still part of the United States.

The Southernmost City in the contiguous United States is a mere four miles by two miles wide. But within that small space sits a world of nightlife, sport fishing, nightlife, watersports, live music, amazing seafood, nightlife, gingerbread architecture, nightlife, and stunning sunsets. Don’t forget that nightlife.

Key West is world-famous for its tropical landscape, literary ties, a historic seaport, the lively atmosphere of Duval Street, and an abundance of watersports and outdoor activities. The island and its southernmost point are popular among family, group, and LGBTQ+ travelers.

Surrounded by the Atlantic Ocean’s coral reefs (the third largest barrier coral reef system in the world, by the way) and the Gulf of Mexico’s sparkling shades of sapphire, emerald, and aqua, Key West is approximately 159 miles southwest of Miami (the closest mainland city) and about 90 miles from Cuba (by water, of course). Visitors frequently tkae part in diving, snorkeling, fishing, paddleboarding, kayaking, and a ton of other water-related activities.

Locals and travelers embrace the island’s eclectic and freewheeling history of pirates, bootleggers, and a wide array of creative former residents with names like Ernest Hemingway, Tennessee Williams, and Jimmy Buffett.

Life is just a little different in Key West –and that’s exactly why we like it! 

Key West 2 Hour Sunset Sail on Schooner America 2.0
1. Key West: 2-Hour Sunset Sail on Schooner America 2.0 Top Recommendation

Sailing is a unique experience, one that brings the adventure of the sea to those who want to try it out. Key West is home to many yacht charters and beautiful vessels, but there's something special about the Schooner America 2.0. This 105-foot tall ship offers tours on both land and water, giving you two very different trips in just one trip. From watching dolphins swim around your boat to seeing Key West from above as you sail with the wind in your hair - this trip will be like no other you've ever experienced!

Key West Hop On Hop Off Trolley Tour
2. Key West Hop-On Hop-Off Trolley Tour

Hop-On Hop-Off Trolley Tour is a fun and convenient way to see everything Key West has to offer. Featuring over 100 stops, you can stay as long or as little as you like at each location. Your expert guide shares the history, lore and legends of Key West with every stop.

Key West Dolphin Watching and Snorkeling Eco Cruise Tour
3. Key West: Dolphin Watching and Snorkeling Eco Cruise Tour

This 45 min cruise departs from the Key West harbor, heading to a cove that is approximately 2 miles away. You will be accompanied by expert guides who will share with you interesting tidbits about dolphins and marine life. As you approach the area, you can expect to see, hear and smell the salty ocean water and observe the relaxing atmosphere of this natural habitat for dolphins, manatees and other marine life .

TL;DR Our Favorite Accommodations in Key West

Best Areas to Stay in Key West, Florida

  • Best area for first-timers/tourists: Uptown
  • Best area for budget travelers: Mid Town
  • Best area for luxury travelers: Sunset Key
  • Best area for safety: Truman Annex
  • Best area for families: New Town
  • Best area for nightlife: Old Town/Downtown

Where to Stay in Key West

1. Best area for first-timers/tourists: Uptown

Key West Butterfly and Nature Conservatory Entrance
image by Sandy Allen

Uptown is an excellent choice if you’re wondering where to stay Key West first time. Uptown is the area around upper Duval and the Southernmost Point in the Continental United States. This southern edge is just a short walk from restaurants, bars, and shops on Duval Street.

Uptown includes the residential Bahama Village, a restored historic district offering an eclectic array of restaurants and shopping options. If you’re planning to stay in Key West, here are a few things to do while you’re there.

Things to do in Uptown

  • Brunch with chickens (yes, really) at Blue Heaven Rendezvous. You’ll probably have to wait in line, so head on over before you get really hangry.
  • Stop in for a slice of key lime pie at the Southernmost Key Lime Shop.
  • Stroll through the historic restored Bahama Village and buy yourself a straw hat or souvenir at the Bahama Village Market.
  • Visit butterflies, birds, and flamingos (Rhett and Scarlett) at the Key West Butterfly and Nature Conservatory.
  • Visit a Civil War fort, exotic plants, and tropical gardens at the West Martello Tower and Key West Garden Club. The fort is listed on the National Register of Historic Places.
  • Go to Higgs Beach, which offers a restaurant, restrooms, a volleyball court, and the Higgs Beach Memorial Pier. There’s also a fenced-in area, Higgs Beach Dog Park, for the four-legged beach bums. The nearby Dog Beach is another place for Fido, Rex, or Spot to run around and sniff.
  • Visit the Key West AIDS Memorial Bridge (at White Street and Atlantic Boulevard), located at the Edward B. Knight Pier. Installed in 1997, granite plaques commemorate the names of people who have died due to complications from AIDS. The original installation held 730 names. Side walls were added in 2014 to allow for more names. As of 2020, there are 1,240 names.
  • Don’t forget to wait in line to pose for a pic with the famous southernmost point waterfront buoy, which proudly proclaims its location: 90 miles from Cuba.

We’ve collected a few ideas for places to stay in Uptown for first-timers. Choose from mid-range options, boutique hotels, and the luxurious hotel and private beach at Casa Marina. Hotels offer beautifully decorated rooms with a private balcony, complimentary breakfast, and a heated swimming pool surrounded by palm trees and tropical flowers.

In addition to the ones featured, the Almond Tree Inn and the Santa Maria Suites are excellent luxury options for an island hotel stay.

Searching for an adults-only hotel when you visit Key West? The Orchid Key Inn offers an outdoor pool, continental breakfast, a bar, and complimentary happy hour. It’s on Duval Street near the southernmost point, making it one of the best hotels for a honeymoon, anniversary, or romantic getaway.

The Caribbean House boutique hotel features colorful rooms with island names and tropical-inspired decor.

See Related: Best Day Trips From Tampa, Florida

2. Best area for budget travelers: Mid Town

Kapok Tree in Key West
image by Sandy Allen

Truman, First, Flagler, and Leon Streets form a rectangle, of sorts, to make up the Mid Town district. Mid Town backs up to New Town and the White Street Gallery District. This town center area consists of residential homes and some vacation rentals and is close to Garrison Bight where the fishing charter boats hang out.

While in any area of town, be mindful of the poultry population (hens, roosters, and chicks). These crowing and cackling creatures are like the squirrels of urban settings. Don’t bother them and they won’t bother you.

They might even pose for a picture, if you’re lucky. Also, lizards and iguanas are frequently seen throughout the Florida Keys. Hey, we said it was different here!

Things to do in Mid Town

  • Book a fishing charter for the day.
  • The Mel Fisher Maritime Museum features treasures from wrecks of Spanish galleons such as the Nuestra Senora de Atocha, the Santa Margarita, and the Henrietta Marie. You can even touch and lift a real bar of gold. Interesting fact: the bar of gold was actually stolen out of its protective plexiglass box at one point (it’s since been returned).
  • The Key West Museum of Art and History at the Custom House is located in an 1890s-era building. Check out local art, photographs, and history exhibits (including items belonging to Ernest Hemingway).
  • The Key West Nature Preserve, while small, is a great way to see mangroves and, possibly, island animals (besides the chickens and lizards). Two boardwalk pathways lead around the area and end at the ocean. It was originally known as The Berg before being acquired by the City.

Mid Town offers a boutique hotel, family-friendly resorts, and luxury Key West hotels with modern amenities such as a continental breakfast, an outdoor swimming pool, and water sports access. Families, groups, and business travelers will find some of the best hotels in this area.

3. Best area for luxury travelers: Sunset Key

Sunset Key and Wisteria Island Aerial View

You can’t get much more luxurious than a private island. For the ultimate luxury experience, book a stay on Sunset Key. Secluded, serene, and situated offshore, it’s 27 acres of tropical island atmosphere.

Sunset is about 500 yards off Mallory Square (you can probably see it while you’re watching the sun slide into the sea). Don’t let the location intimidate you, you can get to Downtown Key West (via a 24-hour private ferry) in about five minutes.

Things to do in Sunset Key

  • Relax in secluded luxury on the white sand beach.
  • Book a couples massage or an indulgent spa treatment. The spa is located at the Opal Key Resort & Marina on the mainland (near Mallory Square).
  • Lounge the day away at the pool or by your private plunge pool.
  • Practice your serve, forehand, and backhand at the tennis courts.

Part of the Opal Collection, Sunset Key Cottages is one of the best hotels in Key West for a luxurious and exclusive experience among a setting of orchids and tropical flowers

One, two, three, and four-bedroom cottages are available. Cottages start around $9,000, which is why we’re not including budget and mid-range for this luxury list (and also because there aren’t any).

See Related: Fun & Best Things to Do in Hollywood, Florida

4. Best area for safety: Truman Annex

Shipwreck Museum Exhibit
image by Sandy Allen (Shipwreck Museum)

While all areas of town are considered safe, we chose Truman Annex due to its gated community access. The area is home to the Truman Little White House (the winter home of Harry S. Truman), making it a good choice to stay in Key West for history enthusiasts.

Truman Annex is just a short walk to the historic seaport, Mallory Square, and the attractions, shopping, and dining of Duval Street.

Things to do near Truman Annex

  • Take a guided tour of the Truman Little White House, Florida’s only presidential museum.
  • Touch rays, feed sharks, and learn about sea turtles at the Key West Aquarium.
  • Spend the day snorkeling, swimming, and sunning at Fort Zachary Taylor State Park. It’s one of the best beaches (and definitely the biggest) on the island. There’s a concession stand, picnic tables, and lots of shady trees to get out of the sun. This is a terrific area to watch dolphins jumping the bow wake of cruise ships heading out to sea.
  • The Key West Shipwreck Museum is filled with artifacts, films, and other items on the history of shipwrecks (including pirate booty like pieces of eight and other coins). You can also climb the lookout tower, but watch out, that vertigo will get ya!
  • Take a selfie by the Mile Marker 0 sign. Yes, you’ll probably have to wait in line. It’s not as popular of a site as the southernmost point, but it can get close.
  • Grab a slice of key lime pie at the Key Lime Pie Bakery. Located near Duval Street, you’ll also find local souvenirs and gift items.

You’ll find family-friendly hotels and weekly vacation rentals in Truman Annex. For a romantic getaway, honeymoon, or special anniversary, an adults-only hotel like the Cabana Inn is a terrific choice and among Key West’s best hotels.

The Hyatt Residence Club has a hotel pool and suites with fully equipped kitchens, which is a great place to stay in Key West for an extended vacation.

5. Best area for families: New Town

Scenery from Fort East Martello Museum
image by Sandy Allen (view from the Fort East Martello Museum)

New Town is the best area to stay in Key West for families who like to be near everything while still being away from the hustle and bustle. It’s the first section of the island of Key West you enter after leaving Stock Island. While most areas of town are fine for families of all sizes, we chose New Town for its proximity to attractions and activities.  

The thing to understand about Key West is that while it’s tropical and Caribbean-like, it’s not really your typical “beach” town. In other words, if you’re a tried-and-true beach bum, you may be a bit disappointed (I have to admit, I kinda was the first time I went – but now I adore it, so all is good).

Let me explain. You won’t find long strands of wide-open beaches like the East and West Coast of mainland Florida. The beaches are small, rocky, and fairly shallow (and often come complete with seaweed).

And you certainly won’t be surfing. That being said, you can still get in the water, relax on a lounge chair, enjoy a tropical drink, and go snorkeling. The shallow aspect will appeal to parents of small children (so, we’ll tally that one up on the plus side).

Smathers Beach or Fort Zachary Taylor State Park are going to be your best bets for beach days.

Things to do in New Town      

  • Grab a hogfish sandwich at the Hogfish Bar & Grill on Stock Island.
  • The Key West Tropical Forest and Botanical Garden is just across the bridge on Stock Isle. Stroll through tropical gardens with exotic flowers, a small pond, and native plants.
  • The Key West Golf Club offers a tropical setting to practice your swing. Golf architect Rees Jones designed the 18-hole par 70 course.
  • Take an Old Town Trolley Tour to learn about island history, Key West’s gingerbread architecture, and other tropical sites around town.
  • Fort East Martello Museum, located in an 1862 Civil War fort, features exhibits on local and maritime history such as cigar making and shipwrecks (as well as some really cool metal sculptures). It’s also home to the supposedly haunted Robert the Doll (the infamous character Chucky was based on him).
  • Book a sightseeing day cruise, snorkeling trip, or sunset booze cruise.
  • Gather the crew and take a day trip to Bahia Honda State Park on Big Pine Key. It’s about 37 miles north of Key West.
  • Relax on the sand at Smathers Beach. There are restrooms, which is a big bonus if you’re traveling with kids.

New Town offers a variety of hotels and resorts with tiki bars, indoor pools, and balconies for budget, mid-range, and luxury travelers. Parrot Key Hotel and Villas, Sunrise Suites Resort Key West, and Fairfield Inn & Suites by Marriott Key West are just a few to choose from.

Located near the Key West International Airport (EYW), Margaritaville Beach House Key West is our favorite Key West resort. It’s one of the best resorts in Key West for families for its on-site restaurant, outdoor pool, hot tub, lawn games, hammocks, and convenience to Smathers Beach (which is right across the street). Kids’ activities include fireside s’mores, fresh-baked cookies, and poolside smoothies while adults get to enjoy rum tastings and paint-and-sip events.

See Related: Best Things to Do in Miami, Florida | Top Attractions

6. Best area for nightlife: Old Town/Downtown

Crowd and a Performer in Mallory Square
Benny Marty / Shutterstock.com

Also called the historic district and historic seaport, Old Town (or downtown Key West) is where you’ll find the nightly sunset spectacle at Mallory Square and the party end of Duval Street (though, the word “party” could apply to all of the island, not just Duval Street). This central location includes the Key West historic seaport.

The famous Duval Street runs from east to west (from the Atlantic to the Gulf of Mexico) through historic Old Town and Downtown to Uptown. While all of Duval Street is alive with nightlife, Old Town is our choice due to world-famous bars like Sloppy Joe’s and the Hog’s Breath (“Hog’s breath is better than no breath at all,” as their slogan so elegantly states).

Things to do in Old Town

  • Take a tour of the Hemingway Home and Museum. The author’s island home is the site where he wrote several novels. Walk through the living room, view his office, and learn about his life and times in the Keys. You may even get a glimpse of the famous six-toed cats.
  • The Key West Lighthouse, built in 1848, is located across from the Hemingway Museum. Climb 88 steps to the top and explore photographs and artifacts from its history.
  • The Tennessee Williams Museum has a large collection of art, books, and other media from the life of the playwright. Williams lived in Key West for about 30 years.
  • Head to the Hog’s Breath Saloon for live music, entertainment, dancing, and drinks. The Hog’s Breath, and Key West in general, has seen impromptu performances by names like Kenny Chesney. You can imagine the crowd that accumulated for that!
  • Soak up that hot Florida sun at Simonton Street Beach or South Beach, one of the smallest on the island.
  • Dance, drink, indulge in excellent food, and listen to live music at nightclubs like Sloppy Joe’s, Margaritaville Restaurant, Fat Tuesday, the Hard Rock Café, Smokin’ Tuna Saloon, Coyote Ugly, and many others.
  • Don’t forget the street performers, arts and crafts vendors, and food kiosks at the nightly sunset celebration at Key West’s Mallory Square during your stay in Key West. After the sun goes down, it’s customary to keep the party going on Duval Street.
  • Check out the waterfront scene along the historic seaport. You’ll find a wide array of fishing charters, sightseeing cruises, and water sports like jet skiing, snorkeling, and diving trips.
  • Get a slice of key lime pie at Kermit’s Key West Key Lime Shoppe. If you’re looking for a recommendation, choose the frozen version that’s covered in chocolate. Sit on the deck and enjoy watching koi swim about.
  • Papa’s Pilar Rum Distillery, located near the Historic Seaport, celebrates “Papa” Hemingway’s love of adventure (and rum) with tours, tastings, cocktail classes, and a shop.

You’ll find a variety of luxury hotels, bed and breakfasts, a historic resort, and vacation cottages close to all the action of Key West’s Old Town. Many claim to be haunted.

Maybe they are, maybe they aren’t. With the variety of famous and infamous individuals frequenting the area, who knows (but it makes for fun stories).

The Artist House on Fleming, Old Town Manor, and the Crown Plaza Key West – La Concha apparently have a ghostly presence. Tennessee Williams and Ernest Hemingway both stayed at the La Concha historic hotel. I thoroughly enjoyed the hotel’s rooftop outdoor pool.

Amsterdam’s Curry Mansion Inn, at Caroline and Duval Street, is a lovely bed and breakfast retreat. Don’t miss the conch-style houses while traveling along Caroline Street on your way to Duval Street.

The Ocean Key Resort is one of the best luxury hotels in the historic seaport. Within walking distance to Mallory Square and the entertainment of Duval Street, it offers a spa, a fitness center, and the Sunset Pier restaurant.

Hotel amenities at these best hotels include free Wi-Fi, outdoor swimming pools, a sun terrace, tropical gardens, and more (the ghosts are a bonus).

FAQ

Where is a good place to stay in Key West near Mallory Square?

For easy access to the city center and the nightly sunset celebrations at Mallory Square while visiting Key West, you’ll want to choose a Key West hotel in Old Town near the water.

What is the best area to stay in Key West?

It’s all about what you want to do! If you need to be near access to watersports, offshore fishing, and such, the historic district of Old Town and the historic seaport are excellent choices. To be within walking distance to dining, shopping, and entertainment on Duval Street, stick with Uptown or Downtown.

What are the best neighborhoods to stay in Key West?

Key West is such a small island, that you’ll be able to easily get from place to place. For a quieter vibe, and one of the best places to stay in Key West, choose Stock Island, which is Key West’s next-door neighbor.

The southernmost point is another excellent area to stay in Key West. Traveling with pets? You’ll want to stay near dog beach in the Uptown area.

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