Where to Stay in Key West

Our Favorite Hotels in Key West

• 5-star: Casa Marina
• 4-star: Lighthouse Hotel
• 3-star: NYAH
• For families: Santa Maria
• For couples: Orchid Key
•

• Near cruise port: Opal Key

a street light on the corner of a street

The Best Area to Stay in Key West

As the southernmost city in the contiguous United States, Key West combines sunlight, culture, and positivity with an off-the-grid sentiment. At under eight square miles, the island is easy to explore, divided between modern, residential New Town and richly atmospheric, historic Old Town. The latter is where most visitors will spend most of their time with several neighborhoods that blend together and borders that aren’t readily recognizable.

With that context, the best area to stay is undoubtably Old Town (also called the Historic District), whether at a picturesque bed-and-breakfast right in the Heart of Old Town or a more lavish hotel located near Downtown,Casa Marina, or the Historic Seaport. No matter the accommodation, Old Town is easy to navigate by foot, the complimentary Duval Loop shuttle, or the Old Town Trolley Tours permitting unlimited boarding all day. Ride-hailing is another low-cost choice for transportation and parking being limited, it`s advisable to leave any automobile back at the lodging.

Key West offers a unique blend of art, history, and a relaxing, waterside atmosphere. While there are other beach-centric vacation spots in Florida, this location still provides some options to enjoy the sand and get your toes wet in the water. The sunsets on the horizon alone are worth visiting, especially when viewed from the daily street celebrations held at Mallory Square. Locals proudly embrace being part of the “Conch Republic” community while following a unifying philosophy that has long welcomed all groups in a way that feels organic and natural. Just be prepared for lively debates on whether Key Lime Pie is better topped with meringue or whipped cream. You may also notice an unusual amount of cats and chickens wandering the sidewalks. Simply accept it. They`ve been around for years.

The Best Places to Stay in Key West

a beach with palm trees and palm trees

Where to Stay in Key West for…

  • Best Neighborhood in Key West for Walking Paths: Heart of Old Town
    The heart of Old Town strictly preserves thousands of colorful wood structures dating back well into the 1800s. Wander around and admire the vintage homes and what seems like a bed-and-breakfast on every corner. The former residence of Ernest Hemingway was converted into a museum that offers an easy tour, whether you want to explore independently or follow a guide. The above-ground cemetery maintains a curiously cheerful atmosphere and though remains active, tourists are welcome. (It’s not unusual to see joggers and bicyclists passing through.) The heart of Old Town serves as a great home base since it’s within walking distance to other neighborhoods in just minutes. So head out on foot and enjoy the stroll.
  • Best Neighborhood in Key West for History: The Truman Annex area
    The principal attraction of the Truman Annex is the previous winter residence of President Harry Truman, which nowadays is the sole presidential gallery in Florida. With much of the decor and furnishings still in place, it`s currently known as the Truman Little White House and features a gift shop for presidential history enthusiasts. The backyard is often utilized 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 has now been converted into the aviation-themed First Flight Island Restaurant & Brewery), the Aquarium, Mel Fisher Maritime Museum, and the Audubon House, which seems preserved in time from 1840 and has a sizable rare-for-the-neighborhood courtyard and garden.
  • Best Neighborhood in Key West for Boating: Historic Seaport
    Various watercraft depart routinely from the Historic Seaport for scenic evening journeys and day trips focused on dolphin watching, swimming, or snorkeling among the reefs. If nothing has been scheduled beforehand, exploring the docks could yield discounted last-minute selections. For an unusual experience, Honest Eco operates the Keys` initial fully electric charterboat. Its uniquely muted voyage also incorporates handcrafted tropical fruit platters. The Key West Express provides service to and from Ft. Meyers and Marco Island along Florida`s western coastline.
  • Best Neighborhood in Key West for Nighttime Activities: 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.

a marina filled with lots of boats on a sunny day

  • Best Neighborhoods in Key West for Food and Dining: Historic Seaport, Bahama Village
    The locals of Blue Bahama Village often overlook this colorful yet tranquil neighborhood, making it easy to miss. However, locals understand Blue Heaven as one of the top spots for breakfast or brunch, where ordering a slice of Key Lime Pie suits the menu equally as the BLT Benedict which substitutes lobster for bacon. Santiago’s Bodega offers fun and quirky Spanish-style snacks for sharing. On the other side of Old Town by the seaport, El Meson de Pepe’s (or as regularly referred, “Pepe’s”) completely emphasizes authentic Cuban cuisine, music, and art. Kermit’s is a small café and gift shop that’s “key lime everything” – not just pie, but cookies, sweets, BBQ sauce, and more. (The inner courtyard with a koi pond and waterfall is a charming place to grab a salad or sandwich.) Seafood place B.O.’s Fish Wagon is renowned for its old truck covered in stickers, but the dishes are somewhat better at Half Shell Raw Bar, which comes with scenic dockside views.
  • Best Neighborhood in Key West for Reaching the Beach: Casa Marina

    • This neighborhood is home to the southernmost point of the contiguous United States, a landmark attraction, as well as the historic Casa Marina hotel. It also sits close to several public beaches along the island`s southern coast, such as expansive Smathers Beach and the more intimate Higgs Beach and Dog Beach, the latter a popular spot for pet owners to relax over cocktails on the deck at Louie`s. Heading west, massive Ft. Zachary Taylor State Park Beach dominates the coastline but sees fewer crowds and caters more to local residents than Smathers Beach.

  • Preferred Neighborhood in Key West for Families: New Town
    After exploring locations and sights during the day, families will want to retreat to New Town, a more peaceful, modern section of Key West. Well-known brands make it simple to stock up on groceries and other provisions, while hotels tend to supply more space and tranquility for your money. A great example is Parrot Key, a tree-lined five-acre hotel renovated from a residential community. First and second floor rooms (which share a common entryway) can be combined into shared accommodations, allowing for plenty of space for large groups and families with children. Upgrade to a room facing the enclosed beach and drift off to sleep in a hammock amid 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 dim streets and odd corners after the sun descends — 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 tranquil and safe guard-gated community.
  • Unsafe Areas of Key West
    Compared to other sunny destinations, Key West has a relatively small homeless population and the Historic District has been declared a “no panhandling” zone. Tourists on foot are advised against wandering the residential blocks between the cemetery and Duval Street. Nor is the area between the cemetery and Casa Marina recommended. Otherwise, use prudent judgment when returning to your hotel after partaking in the late-night festivities. Transportation is convenient and affordable, so take advantage after dark.

The 8 Best Neighborhoods in Key West for Tourists

a large group of people walking down a street

1. Duval Street

Duval Street extends from one end of Old Town to the other. Depending on one`s perspective, the road passes through Casa Marina, Heart of Old Town, and where the Truman Annex area merges with the Historic Seaport. One could walk the entire street and gain a good sense of Key West. It’s the most lively area at night and full of 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 exploring around town. The Duval Loop is a free shuttle that covers the entire road and a few surrounding blocks. Take advantage of it.

  • Beltane Fire Festival – Hosted annually at the end of April on Calton Hill, the Beltane Fire Festival is a modern interpretation and reimagining of an ancient Celtic ritual from the Iron Age. The largest event of its type, it starts with an elaborate procession and involves a bonfire, live music, dancing, and ample food and drink for enjoyment.
  • Best Budget/Moderate Hotel: La Te Da

2. Downtown/Historic Seaport

The harbor at the Historic Seaport is an eclectic yet commercial blend of boating, dining and shopping. The Sails to Rails museum is an inexpensive detour worth exploring to learn how transportation was modernized and the Keys were connected by railroad. Neighboring Mallory Square is renowned for its street performers and daily sunset viewings, perhaps best experienced from the rooftop bar at the Margaritaville hotel. Between the boats and crowds, it’s the one time of day when it seems like everyone in Key West is all in one place.

3. Heart of Old Town

The center of the Old Town region is also considered the heart of Key West`s restoration movements, with much of the architecture dating back to the early-to-mid 1800s. Many buildings, now bed-and-breakfast hotels, offer options for those wanting to “live like a local” for a few days. Keep in mind some B&Bs have restricted parking, so verify availability in advance for those traveling by car. The Heart of Old Town is the most centralized neighborhood, benefiting travel around Key West which relies heavily on walking. Nearby attractions include the historic cemetery or Secret Garden parrot sanctuary with a quirky flair, but the neighborhood blends seamlessly with the bars, shops, and restaurants of Duval Street and Bahama Village.

4. Casa Marina

The locale grew around the primary resort, constructed in 1920 by an important railroad businessman. The facility is impressive architecturally and has its own beach and expansive pool area. The area extends northward toward the island’s most consistent beachfront strip (notably, Smathers Beach), though it is most known for the large concrete symbol marking the southernmost point of the continental United States. Join others to have your photograph taken here. Mornings appear best to avoid long waits. After, walk over to the Butterfly and Nature Conservatory to see the flamingos.

5. Bahama Village

Bahama Village provides a refreshed environment apart from the crowded attractions along Duval Street. The Blue Heaven restaurant features a delightful outdoor space decorated with quirky embellishments and roaming roosters between tables situated on sandy ground. Guests are also within steps of popular destinations such as the Key West Lighthouse offering panoramic views of the island. The Ernest Hemingway House is located directly across the street and shares similar vistas from the second level. Additionally, travelers may find some Bed and Breakfast accommodations in the area, such as Caribbean House, offering slightly more affordable pricing compared to other sections of Old Town.

6. Truman Annex

Truman Annex is a privately secured residential community where numerous homes have been renovated from former military structures. The neighborhood experiences especially tranquil nights with a heightened sense of security. You may come across a handful of temporary rentals through online services, even though the city encourages bed-and-breakfast establishments instead. The primary attraction here is the Little White House, frequently used by President Truman as his winter quarters during World War II. It’s now an educational museum that history aficionados will want to visit, who will also appreciate touring the USCGC Ingham Maritime Museum developed from an antique naval vessel. The waterfront Key West Amphitheater regularly hosts national performers year-round.

7. New Town

New Town (which integrates with residential Poinciana Plaza in the northwest half of Key West) is an abrupt change of atmosphere from the historic Old Town neighborhoods. It’s where the island starts to feel like other parts of the United States with present-day housing and shopping complexes. While it’s an easy place to stock up groceries (or go to Home Depot — sometimes supplies are needed), New Town also has its share of waterfront hotel options allowing guests to extend their budget a little further. The neighborhood is the closest proximity to the small but convenient Key West International Airport.

8. Sunset Key

Sunset Key is a privately held tropical isle near Key West that can be reached solely via ferries generally departing twice per hour. The uniqueness of lodging on a small, secluded 27-acre island has appeal, but the mix of resort and residential cottages is strictly for the luxury traveler with ample funds to spend. Latitudes is a fine-dining restaurant requiring reservations for evenings with rum tastings.

The Best Beaches in Key West

Key West is renowned for its charm and way of living more than its beaches. Yet, the ones scattered around this small island have their own unique personality and attributes. If you love to lounge in the sand and take a dip in the water, map out your visit based on the beaches that best suit you.

  • Best Beach for Swimming: Smathers Beach
    The most substantial free 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 basically 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 Path in Casa Marina, this beach is petite but gets its name from the canines and owners who appear to play in the water and run on the sand. Louie’s is a fun spot next door for sipping on happy-hour beverages on an outdoor deck overlooking the water.
  • Higgs Beach has soft sand for basking in the sun in Key West.

    • In close proximity to the lively Smathers Beach but with less crowds, Higgs Beach provides a pleasant setting simply to unwind and take in the sunshine. Nearby on the roadside is a memorial paying tribute to African refugees and their contributions to Key West. On the other side of the pier lies the even more secluded and tranquil Rest Beach.

  • Ft. Zachary Taylor Beach has plenty of shade in Key West.

    • As part of a state park, the Ft. Zachary Taylor Beach is a favorite of locals who appreciate its scale 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 ideal 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

a beach with palm trees and palm trees

While Key West has its own convenient international airport, it’s common for visitors to drive down from the Florida mainland, whether they fly into Miami first or not. It’s a scenic drive that takes about 3 hours. There’s quite a bit to see and breaks in the trip may be desired 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 islands and can be easily accessed by car from the Miami area. It is renowned for swimming, diving, and snorkeling activities. The Coral Restoration Foundation operates on a voluntary basis working to help reverse the harm and deterioration inflicted on the coral reef ecosystem. (They always welcome help from scuba divers interested in ecotourism, which can potentially qualify as a tax deduction.) Key Largo offers various hotels, from large to small in size. The most luxurious accommodation is the Bungalows, the sole all-inclusive resort located in the keys. The rooms are completely new, incredibly clean, and come with private outdoor spaces including a bathtub and shower under the open sky.
    Best hotel in Key Largo: Playa Largo Resort & Spa
  • Islamorada
    This city occupies five smaller islands and provides a great chance to appreciate the sunny conditions while experiencing fewer crowds. Cheeca Lodge is a historically significant beachfront resort built in 1946. It was a favorite destination of former President George H.W. Bush, possessing a suite named in his honor. Advance booking is nearly always necessary for the suite. Some rooms feature a hot tub on the verandah. The Islander resort gives off nearly the atmosphere of a motor lodge (with private parking space for each room), but has undergone extensive renovations and demonstrates remarkable eco-friendliness with the largest solar panel array in the Keys and vibrant, colorful gardens.
    Top hotel in Islamorada: Fisher Inn Resort & Marina
  • Duck Key
    Small and secluded, Duck Key is entirely south of the main highway. If you want to remain at a single resort, Hawks Cay is a great choice, offering a strong children`s program (featuring a pirate ship replica by the splash pool) and a private dolphin habitat. Be sure to sample the locally caught fresh fish, usually harvested the same day, at Angler & Ale.
    The top hotel in Ducks Key is the Hawks Cay Resort, which has rooms well suited for families of 4-5 with bunk beds.
  • Marathon
    Another populated city expanded over various keys, Marathon stands as one of the optimum destinations southern of the mainland for fishing. Grassy Flats is an intimate eco-accommodating boutique lodge that comes with a hands-on contact and excellent cocktails at the poolside tiki bar. Isla Bella is a broader, new ultra-luxury resort that has flawless views of sunsets from the private beach. Visit the historic Castaways Restaurant where fresh fish is often provided as sashimi, like the must-try lionfish. Keys Fisheries is a dockside restaurant renowned for its key lime pie, lobster reuben sandwich, and fresh stone crab. Visit the Turtle Hospital that nurses unwell and harmed sea turtles back to health. Tours are very popular.
  • Capitol Hill Block Party – A three-day music and arts festival featuring food, beer gardens, and over 100 local and international artists performing at indoor and outdoor venues.
  • Stock Island
    The key directly to the north of Key West is recognized as the home to the working class. Housing costs are notably more reasonable and lodging is now starting to emerge. The Perry is a new ultra-modern resort of steel and concrete with reclaimed wood and other rustic touches. It sits alongside a 220-berth marina and offers 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 regularly sell out by afternoon.
    Best hotel in Stock Island: The Perry

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Welcome to my travel website! I’m Mary Howard, an American who has been exploring the world full-time for 8 years.

Together with my husband, Intan, we often find ourselves in our second home, Bali, but our adventures take us to exciting destinations all over the globe.

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