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Updated: March 29, 2021
The Best Area to Stay in Key West
As the southernmost city in the continental United States, Key West combines sun, culture, and positive energy with an off-the-grid feel. At less than eight square miles, the island is easy to explore, divided between contemporary, residential New Town and character-rich, historic Old Town. The latter is by far where visitors will spend the majority of their time with several neighborhoods that frequently blend together and borders that aren’t always easy to identify.
With that in mind, Old Town (also known as the Historic District) is the best area to stay, whether it’s a charming bed-and-breakfast in the Heart of Old Town or a more luxurious hotel in and around Downtown, Casa Marina, or the Historic Seaport. No matter where you stay, Old Town is easy to navigate on foot, the free Duval Loop bus shuttle, or the Old Town Trolley Tours with unlimited reboarding all day long. Ride-sharing services are another inexpensive option for getting around and with parking tight, it’s best to leave any car back at the hotel.
Key West is a unique mix of art, history, and an easy, waterside atmosphere. There are other more beach-oriented vacation spots in Florida, but you still have a few options for enjoying the sand and dipping your toes in the water. The horizon sunsets alone are worth a visit, especially when viewed from the daily Mallory Square street celebrations. Locals take an independent pride in being part of the “Conch Republic”, yet follow a “One Family” mentality that has long welcomed all demographics in a way that feels organic and effortless. Just be ready for a fierce debate on whether Key Lime Pie should be topped with meringue or whipped cream. You may also notice an unusual amount of cats and chickens roaming the sidewalks. Just go with it. They’ve been around for years.
The Best Places to Stay in Key West
- Best Luxury Hotels in Key West
Casa Marina • H20 Suites • Hyatt Residence Club
- Best Boutique Hotels in Key West
Orchid Key Inn • Gardens Hotel • Kimpton Lighthouse Hotel • Weatherstation Inn • Southernmost House
- Best Cheap Hotels in Key West
NYAH • Seashell Motel • Fairfield Inn
- Best Hotels for Families in Key West
Santa Maria Suites Resort • Oceans Edge Key West
Where to Stay in Key West for…
- Best Neighborhood in Key West for Walking: Heart of Old Town
The Heart of Old Town is where the preservation guidelines are strictest with thousands of colorful wood structures dating back well into the 1800s. Wander around and admire the vintage homes and what feels like a bed-and-breakfast on every corner. The former home of Ernest Hemingway was converted into a museum that makes for an easy tour, whether you want to explore it yourself or follow a guide. The above-ground cemetery is curiously cheerful and although it’s still in operation, tourists are welcome. (It’s not uncommon to see joggers and bicyclists traveling through.) The Heart of Old Town is a great home base since it’s walkable to other neighborhoods in just minutes. So head out on foot and enjoy the stroll.
- Best Neighborhood in Key West for History Buffs: Truman Annex
The main attraction of the Truman Annex is the former winter residence of President Harry Truman, which today is the only presidential museum in Florida. With much of the decor and furniture still in place, it’s now known as the Truman Little White House and includes a gift shop for presidential history buffs. The backyard is frequently used as an event space. Walk toward Mallory Square and the Historic Seaport and you’ll come across the original headquarters of Pan Am airlines (which is now the aviation-themed First Flight Island Restaurant & Brewery), the Aquarium, Mel Fisher Maritime Museum, and the Audubon House, which feels preserved in time from 1840 and has a large rare-for-the-neighborhood courtyard and garden.
- Best Neighborhood in Key West for Boating: Historic Seaport
Charters ranging from yachts to sailboat schooners leave frequently from the Historic Seaport for sunset cruises and day trips for dolphin watching, swimming, or snorkeling among the reefs. If you haven’t booked anything in advance, walk the docks and you might be offered a discount on the spot. For something different, Honest Eco has the Key’s first all-electric charter. It’s an unusually quiet ride and the hand-carved fruit platters are a nice touch. The Key West Express has rides to and from Ft. Meyers and Marco Island along the west coast of Florida.
- Best Neighborhood in Key West for Nightlife: Downtown/Duval Street
Duval Street is the heart of the Downtown area and where the action is for bars, restaurants, and nightclubs. On any given night, you’ll find live acts performing at the Smokin’ Tuna Saloon, Hog’s Breath Saloon, Irish Kevin’s, or the historic Sloppy Joe’s, which was said to be a favorite of Earnest Hemingway before it expanded into a large party house atmosphere with slushy cocktails. The Green Parrot is all about jazz and blues with irreverent charm seen immediately in the “Sorry, We’re Open” sign. Rick’s is eight bars in one, including an upstairs nightclub, downstairs rock bar, and next-store strip club. The intersection of Duval and Petronia marks the Pink Triangle of LGBTQ-friendly party spots, including 801 Bourbon Bar, New Orleans House/Bourbon St. Pub, and Aqua Nightclub, which all mix in plenty of entertainment. New Orleans House is also home to the famous red shoe drop on New Year’s Eve.
- Best Neighborhood in Key West for Food and Restaurants: Historic Seaport, Bahama Village
Tourists sometimes overlook the small Bahama Village neighborhood, which is colorful but so low-key that it’s easy to miss. Locals, however, know Blue Heaven is one of the best spots for breakfast or brunch, where ordering a slice of Key Lime Pie is just as appropriate as the BLT Benedict (with the “L” standing for lobster). Santiago’s Bodega is fun and quirky with Spanish-style tapas for sharing. On the other side of Old Town by the seaport, El Meson de Pepe’s (or as most seem to call it, “Pepe’s”) is all about authentic Cuban food, music, and art. Kermit’s is a small café and gift shop that’s “key lime everything” — not just pie, but cookies, candies, BBQ sauce, and more. (The inner courtyard with a koi pond and waterfall is a charming spot to grab a salad or sandwich.) Seafood spot B.O.’s Fish Wagon is famous for its old truck covered in stickers, but the dishes are slightly better at Half Shell Raw Bar, which comes with scenic dockside views.
- Best Neighborhood in Key West for Hitting the Beach: Casa Marina
This neighborhood is home to the Southernmost Point of the Continental United States (an almost required photo stop) and the beautiful historic Casa Marina hotel. Yet it’s also close to several public beaches on the south end of the island, including the expansive Smathers Beach, smaller Higgs Beach, and tiny Dog Beach, which brings out pet owners and is a fun spot for cocktails on the deck at Louie’s. In the other direction, Ft. Zachary Taylor State Park Beach dominates the western coast, but is more secluded and tends to be more locals-oriented than Smathers Beach.
- Best Neighborhood in Key West for Families: New Town
After visiting sites and attractions during the day, families will be eager to retreat to New Town, a more quiet, contemporary section of Key West. Familiar chains make it easy to stock up on groceries and other supplies, while hotels tend to provide more space and serenity for your dollar. A great example is Parrot Key, a tree-lined five-acre hotel renovated from a residential townhome community. First and second level rooms (which share a common foyer) can be combined into shared accommodations, opening up plenty of space for large groups and families with children. Upgrade to a room on the enclosed beach and fall asleep on a hammock between palm trees.
- Safest Areas of Key West
Key West is incredibly safe. Walking around in busy areas day or night is rarely a problem. Stay away from dark streets and odd corners after the sun goes down — not that you’ll want or need to do that anyway — and you’ll have few issues. Busy tourist areas like Duval Street and the Historic Seaport have little to worry about when it comes to safety. The Truman Annex is a very quiet and safe guard-gated community.
- Unsafe Areas of Key West
Compared to other sunny destinations, Key West has a small homeless population and the Historic District is designated a “no panhandling” zone. The residential blocks between the cemetery and Duval Street aren’t recommended for tourists on foot. Neither is the area between the cemetery and Casa Marina. Otherwise, make sure to use your best judgment when returning to your hotel after enjoying the late-night party scene. Transportation is easy and affordable, so take advantage of it after dark.
The 8 Best Neighborhoods in Key West for Tourists
1. Duval Street
Duval Street runs from one end of Old Town to the other. Depending on how you look at it, the road runs through Casa Marina, Heart of Old Town, and where the Truman Annex area merges with the Historic Seaport. You could walk the entire street and get a good feel for Key West. It’s the most active area at night and loaded with nightlife. The bars and gift shops are especially targeted at tourists, so if you have the time, use the street as a starting point for venturing around town. The Duval Loop is a free shuttle that covers the entire road and a few surrounding blocks. Take advantage of it.
The marina at the Historic Seaport is an eclectic yet commercial mix of boating, restaurants and shops. The Sails to Rails museum is an inexpensive detour worth exploring to learn how the Keys were modernized and connected with the railroad system. Neighboring Mallory Square is famous for its street performers and daily sunset viewings, perhaps best enjoyed from the rooftop bar at the Margaritaville hotel. Between the boats and crowds, it’s the one time of day when it feels like everyone in Key West is all in one place.
The Heart of Old Town is also the heart of Key West’s restoration movement, with much of the architecture dating back to the early-to-mid 1800s. Many of the buildings, which are now bed-and-breakfast hotels, offer plenty of options for those looking to “live like a local” for a few days. Keep in mind, some B&Bs have limited parking, so if you’re traveling with a car, check about availability in advance. The Heart of Old Town is the most centralized neighborhood, which is a perk because getting around Key West is based heavily on walking. Some of the nearby attractions are on the quirky side, like the historic cemetary or the Secret Garden parrot sanctuary, but the neighborhood merges effortlessly with the bars, shops, and restaurants of Duval Street and Bahama Village.
4. Casa Marina
The neighborhood developed around the Casa Marina Hotel, built in 1920 by railroad tycoon Henry Flagler. The resort is a stunning piece of architecture and has its own beach and expansive backyard pool deck. The neighborhood winds north toward the island’s most consistent stretch of beachfront (most notably, Smathers Beach), yet it’s best known for the large concrete buoy that marks the southernmost point of the continental United States. Get in line and have your photo taken. Mornings seem best for avoiding a long wait. When you’re done, walk over to the Butterfly and Nature Conservatory to see the flamingos.
Bahama Village is the best quick escape from the tourist trap elements of Duval Street. The Blue Heaven restaurant has a fantastic sandy courtyard with quirky outdoor décor and roosters roaming between tables. You’re also steps from tourist attractions like the Key West Lighthouse which has the best views of the island. The Ernest Hemmingway house is right across the street and has similar views from the second floor. Otherwise, you may find a few B&B options, like Caribbean House, which are a bit less expensive than elsewhere in Old Town.
6. Truman Annex
Truman Annex is a private guard-gated community where many of the homes were renovated from old military buildings. The neighborhood is especially peaceful at night with a sense of added security. You may find a few Airbnb rentals, although the city discourages them in favor of bed-and-breakfasts. The main attraction here is the Little White House, used frequently by President Truman as his winter residence during World War II. It’s now a museum and a must-visit for American history buffs who will also love the USCGC Ingham Maritime Museum, designed from a vintage military vessel. The waterside Key West Amphitheater welcomes national touring acts throughout the year.
7. New Town
New Town (which merges with residential Poinciana Plaza in the northwest half of Key West) is an abrupt change of pace from the historic Old Town neighborhoods. It’s where the island starts to feel like the rest of the United States with contemporary housing and shopping plazas. While it’s an easy place to stock up groceries (or go to Home Depot — sometimes you need that), New Town also has its share of waterfront hotel options allowing guests to stretch their dollar a bit further. The neighborhood is the closest to the small but convenient Key West International Airport.
8. Sunset Key
Sunset Key is a privately-owned island near Key West that’s only reachable by ferries that typically run twice an hour. The novelty of staying on a small, isolated 27-acre island has its appeal, but the mix of resort and residential cottages is strictly for the luxury traveler with money to spend. Latitudes is a fine-dining reservations-only restaurant with evening rum tastings.
- Best Hotels: Sunset Key Cottages
The Best Beaches in Key West
Key West is known for its charm and lifestyle more than its beaches. Yet, the ones scattered around this small island have their own unique identity and characteristics. If you love to lounge in the sand and take a dip in the water, map out your visit based on the beaches that work best for you.
- Best Beach for Swimming: Smathers Beach
The largest public beach in Key West is popular for kite-flying, water sports, and swimming, although like most beaches facing the Atlantic, the water is shallow and waves are virtually non-existent due to the coral reef. Smathers Beach is next to the ruins of a Civil War-era fort overseen by the Key West Garden Club as a free attraction. It’s an inviting spot for escaping the sun and finding a bit of shade. Parking is easy but be ready to feed the meter.
- Best Beach for Pets: Dog Beach
At the south end of Vernon Avenue in Casa Marina, this beach is tiny but gets its name from the dogs and owners who come to play in the water and run on the sand. Louie’s is a fun spot next door for sipping on happy-hour cocktails on an outdoor deck overlooking the water.
- Best Beach to Sunbathe: Higgs Beach/Rest Beach
Close to Smathers Beach, but less busy, Higgs Beach is a good spot to simply relax and enjoy the sun. Near the road is a memorial to African refugees and their contributions to Key West. On the other side of the pier is Rest Beach, which is even more quiet and secluded.
- Best Beach for Shade: Ft. Zachary Taylor Beach
As part of a state park, the Ft. Zachary Taylor Beach is a favorite of locals who appreciate its size and the entry fee that keeps out large crowds of tourists. The beach is banked against a large grove of Australian pine trees offering plenty of shade. Hang out on the sand and watch the boats as they head out toward the Atlantic from the seaport.
- Beach Beach for a Quick Dip: Simonton Street Beach
Another local favorite, Simonton Street Beach is very small and one of the few that faces the Gulf of Mexico. It’s a great vantage point for watching sunsets and grabbing a cocktail at one of several nearby bars and restaurants. Restrictive netting keeps swimmers from traveling out too far.
The Best of the Florida Keys
While Key West has its own convenient international airport, it’s common for visitors to drive down from the Florida mainland, whether or not they fly into Miami first. It’s a scenic drive that takes about 3 hours. There’s quite a bit to see and you may want to break up the trip with an overnight hotel stay along the way. Many of the keys are worth the overnight stay.
- Key Largo
Key Largo is the largest of the Florida Keys and an easy drive from the Miami area. It’s known for swimming, diving, and snorkeling. The Coral Restoration Foundation is a volunteer operation working to help reverse the damage and deterioration done to the coral reef. (They’re always welcoming diving help from those interested in ecotourism, which can potentially make your vacation a tax write-off.) Key Largo has plenty of hotels, large and small. The most luxurious is the Bungalows, the only all-inclusive resort in the keys. The rooms are brand new, ultra clean, and come with private courtyards that include an outdoor bathtub and shower. Best hotel in Key Largo: Playa Largo Resort & Spa
This city is spread out over 5 smaller keys and is a great option for enjoying the sunny weather with fewer crowds. Cheeca Lodge is a historic resort on the beach built in 1946. It was a favorite of President George H.W. Bush and even has a suite named after him. (Ask about it well in advance. The suite is almost always booked.) Some rooms come with a hot tub on the balcony. The Islander resort almost has a motor lodge feel (with individual parking for each room), but has undergone extensive renovations and is incredibly eco-friendly with the largest solar panel installation in the Keys and beautiful, colorful gardens. Best hotel in Islamorada: Fisher Inn Resort & Marina
- Duck Key
Small and secluded, Duck Key is entirely south of the main highway. If you’re looking to just stick around one resort, make it Hawks Cay, which has a great kids program (with a pirate ship replica by the splash pool) and a private dolphin enclave. Make sure to have some fresh fish, usually caught the same day, at Angler & Ale. Best hotel in Ducks Key: Hawks Cay Resort (rooms with bunk beds are great for families of 4 or 5)
Another city spread out over several keys, Marathon is one of the best destinations south of the mainland for fishing. Grassy Flats is an intimate eco-friendly boutique resort that comes with a hands-on touch and great cocktails at the poolside tiki bar. Isla Bella is a larger, new ultra-luxury resort that has perfect sunset views from the private beach. Visit the historic Castaways Restaurant where fresh fish is often served as sashimi, including the must-try lionfish. Keys Fisheries is a dockside restaurant known for its key lime pie, lobster reuben sandwich, and fresh stone crab. Visit the Turtle Hospital that nurses sick and injured sea turtles back to health. Tours are very popular. Best hotel in Marathon: Tranquility Bay Resort (two and three-bedroom houses on the beach)
- Stock Island
The key directly north of Key West is known as where the working class live. The housing is considerably more affordable and hotels are now starting to pop up. The Perry is a new ultra-modern resort of steel and concrete with reclaimed wood and other rustic touches. It sits alongside a 220-slip marina and has free guest shuttles to Key West. While in Stock Island, find time to try the woodfired pizza at Roostica and the key lime beignets at Croissants de France, which often sell out by afternoon. Best hotel in Stock Island: The Perry
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