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Key West is the southernmost city of the continental United States and one of Florida’s most popular tourist destinations. In the 1930s, it was home to famed novelist Ernest Hemingway, and today visitors flock to Key West to enjoy the area’s lively nightlife and thriving watersports scene. The city boasts beautiful sandy beaches, elegant conch-style architecture, and a thriving arts scene.
If you’re planning to visit Key West for the first time, you might wonder which part of the city to stay in. In this travel guide, we look at where to stay in Key West and who each area is best suited to. Plus, we highlight some of the city’s best hotels to help you plan your visit to this popular region of the Florida Keys.
Old Town for Historic Charm
Highlights: Key West City Cemetery, Secret Garden Parrot Sanctuary
With architecture dating back to the 1800s, Key West’s Old Town has a quaint, historic atmosphere that is protected by the area’s strict preservation guidelines. The area is highly walkable, and many popular parts of the city, such as Southernmost Point and Duval Street, are within walking distance.
If you’re looking for a quiet and characterful place to stay, make it Old Town. Many of the colorful wooden buildings here are bed-and-breakfast hotels, so you won’t have trouble finding accommodations offering a hearty meal to get your day started right.
Popular Accommodation in Old Town
Southernmost Beach Resort and Guesthouse
This serene resort feels somewhat separate and private from the rest of Old Town, which makes the Southernmost Beach Resort and Guesthouse perfect for a peaceful getaway. It offers garden-view and ocean-view rooms, four dining venues, wine-tasting classes, and live music shows.
Hyatt Centric Key West Resort and Spa
With many of its 120 spacious rooms offering impressive views of the Gulf of Mexico, Hyatt Centric Key West Resort and Spa is a relaxing resort with a casual atmosphere. Amenities include a seafood grill, a full-service bar, a spa, and access to snorkeling and golf.
Kimpton Key West
There are five Kimpton hotels dotted across the heart of Old Town, including the Kimpton Lighthouse Hotel. Each has its own unique style and atmosphere. Set in lush gardens with beautiful swimming pools, each Old Town hotel from Kimpton provides a taste of local Key West life.
H2O Suites
The H2O Suites is a serene adults-only boutique hotel with luxury accommodations and excellent modern amenities. Enjoy panoramic views of Key West as you sip cocktails beside the pool on the rooftop deck.
Mallory Square for Daily Sunset Celebrations
Highlights: Key West Aquarium, Key West Shipwreck Museum, Key West Historic Memorial Sculpture Garden, Mel Fisher Maritime Museum, Key West Museum of Art & History
Mallory Square sits at the end of lively Duval Street on Old Town’s historic waterfront. It’s home to many popular restaurants and bars and several fascinating attractions. Plus, you can enjoy incredible sunset views over the Gulf of Mexico when you head here in the evening.
Each night, two hours before the sun goes down, the square fills up with tourists, food carts, art and craft exhibitors, and street performers, creating a lively, celebratory atmosphere that’s not to be missed.
Popular Accommodation in Mallory Square
Ocean Key Resort & Spa
Overlooking Sunset Pier, the Ocean Key Resort & Spa is a timeless island-style hotel within walking distance of many popular Mallory Square bars and attractions. Plus, there’s a full spa, an outdoor pool and hot tub, and a waterfront restaurant.
Duval Street for Lively Nightlife
Highlights: Sloppy Joe’s Bar, Jimmy Buffett’s Margaritaville, Ernest Hemingway Home & Museum, Southernmost House
Duval Street cuts right through the heart of Old Town, from north to south. It’s one of the busiest and liveliest streets in the area, with no shortage of bars, restaurants, boutique shops, museums, and tourist attractions.
It also provides fantastic nightlife. Sloppy Joe’s is a particularly well-known bar that is said to have been the favorite drinking hole of Ernest Hemingway. You can also find live music and entertainment in the many jazz, blues, and rock clubs here. If you want a taste of Key West’s party atmosphere, definitely make Duval Street your base.
Popular Accommodation near Duval Street
Pier House Resort & Spa
The Pier House Resort & Spa is a four-star luxury hotel and spa that has a private beach with its own bar, two restaurants with beautiful ocean views, and an outdoor swimming pool.
The Guesthouses by Southernmost Beach Resort
Avalon and Duval Gardens are two guesthouses owned by Southernmost Beach Resort. These charming historic properties offer the lively atmosphere of Duval Street along with access to the resort’s peaceful and luxurious private beaches and pools.
Historic Seaport for Sightseeing and Water Sports
Highlights: Sails to Rails Museum
Key West’s Historic Seaport lines the island’s northwestern edge and is dotted with restaurants, bars, and attractions. You can take cruises and boat trips from here if you’re interested in dolphin watching or snorkeling.
This is also where you’ll head to catch ferry rides to Fort Meyers and Marco Island on Florida’s west coast. Historic Seaport is a convenient base for many of Key West’s biggest attractions, as well as easy access to water sports like sailing, parasailing, fishing, and snorkeling.
Popular Accommodation in Historic Seaport
Opal Key Resort & Marina
With rooms that feature floor-to-ceiling windows, the Opal Key Resort & Marina is a bright and airy hotel and a contemporary and relaxing place to stay. It includes 24/7 room service, suites with whirlpool tubs, a gym, a restaurant, and an outdoor pool.
Casa Marina for Pure Luxury
Highlights: Higgs Pier, Higgs Beach, African Refugee Cemetary
The Casa Marina Hotel, by the Curio Collection for Hilton, was built in 1920 by a railroad tycoon, and the neighborhood surrounding it quickly became known by the same name. The area stretches between Southernmost Point and Edward B. Knight Pier and spans some popular public beaches. This is a good base if you’re looking for sun, sea, and sand, but note that it has an upmarket atmosphere, and it’s pricier than other parts of the city.
Popular Accommodation in Casa Marina
Casa Marina Key West Resort by Hilton
This luxury resort is situated right on the oceanfront and boasts an exclusive private beach. The Casa Marina Key West is one of the most famous hotels in the area, with its timeless architecture and decor.
New Town for Budget Vacations
Highlights: Key West Tropical Forest & Botanical Garden
New Town is a quiet, modern neighborhood that’s far more affordable than Key West’s historic district. There are some beachfront hotels in the area for those looking for ocean-view rooms, and they tend not to get booked up as far in advance as those in the Old Town if a last-minute trip is on the cards.
New Town also benefits from being close to Key West International Airport. There aren’t many sights here, and you’ll likely need a car to get around, but if you’re looking for a quiet and affordable way to visit Key West, New Town is a good place to stay.
Popular Accommodation in New Town
Parrot Key Hotel & Villas
With cottage-style rooms and lush tropical gardens, the Parrot Key Hotel & Villas is a spacious waterfront resort that offers a peaceful escape from the city. Plus, it provides complimentary shuttles to Duval Street and Smathers Beach to help guests get around.
The Laureate Key West
The Laureate Key West is a new, upscale resort that offers haven-like suites with gorgeous views of the Salt Pond Keys. It’s ideal for those looking for modern luxury.
Fairfield Inn & Suites by Marriot Key West
The Fairfield Inn & Suites by Marriot Key West is an inviting hotel that provides free WiFi in all guest rooms and a free buffet breakfast each day. It has a 24-hour fitness center and an outdoor pool with a poolside tiki bar.
Havana Cabana at Key West
The Havana Cabana at Key Key West is a charming hotel features classic cars out front and nostalgiac design influences from neighboring Cuba. It boasts the largest swimming pool in Key West, where you can sip cocktails as you relax poolside.
Smathers Beach for Sun, Sea & Sand
Highlights: Fort East Martello Museum
Smathers Beach is Key West’s largest public beach. It stretches for two miles on the south side of the island, and its golden sand and rows of palm trees make it instantly recognizable.
Smathers is popular with tourists and locals alike for sunbathing, playing beach sports like volleyball, and heading out into the waves for jetskiing. If you’re looking for a beach-focused vacation, staying at Smathers Beach is a great choice, but you’ll need to drive or Uber when you want to head to Old Town for sightseeing.
Popular Accommodation in Smathers Beach
Margaritaville Beach House
For the ultimate beachfront getaway, check in to Margaritaville Beach House, which sits just across from Smathers Beach. Many of the hotel’s spacious suites have private balconies with Atlantic Ocean views, and there’s a restaurant, a bar, and a lagoon-style pool area to enjoy.
Sunset Key for Private Escapes
Highlights: Sunset Pool
Sunset Key is a privately-owned, 27-acre island situated northwest of Key West. It was originally built during the cold war to service submarines and other vessels. Today, it’s dotted with luxury vacation rentals.
A word of warning: you’ll be very isolated when you stay on Sunset Key and totally reliant on twice-hourly ferries to reach Old Town. The quiet and privacy here appeal to couples and families looking for a luxurious, private escape in the Florida sunshine.
Popular Accommodation in Sunset Key
Sunset Key Cottages
These luxury cottages are nestled among tropical gardens and offer the utmost privacy and panoramic views of the Gulf. The resort has a spa, a gourmet restaurant, a pool bar, and tennis courts.
Stock Island for Golf and Sailing
Highlights: Key West Golf Club, Key West Tropical Forest & Botanical Garden
Stock Island lies east of Key West, and it offers a far quieter pace of life than the bustling streets of Old Town. It’s also significantly cheaper when it comes to accommodation options.
Stock Island is primarily a residential area but is also home to several marinas and offers extensive boat storage and rentals. The island has a thriving art scene and a popular golf course, and during December, it hosts a 3-day festival promoting local artists and businesses. Stock Island is accessible via road thanks to the Overseas Highway, which cuts right through its center and connects it with Key West.
Popular Accommodation on Stock Island
The Perry Hotel & Marina
The Perry Hotel & Marina is an extensive resort includes a deep water marina for guests to dock their boats, as well as waterfront pools, a gym, dockside restaurants, community gardens, dog parks, and access to shuttle rides to Old Town.
Truman Annex for History Lovers
Highlights: Truman Little White House, Truman Annex Park, USCGC Ingham Maritime Museum, Key West Amphitheater, Fort Zachary Taylor Historic State Park
The Truman Annex is a luxurious gated community that was once home to President Harry Truman. His former winter residence, now known as the Little White House, is open as a museum, with much of the original decor and furniture remaining. There are a few hotels and guesthouses in the Truman Annex area, and these are best suited to those looking for a quiet, safe neighborhood from which to explore Old Town’s historic sights.
Popular Accommodation in the Trump Annex
Weatherstation Inn
The Weatherstation Inn is five bedroom adults only Bed & Breakfast. Its location is part of its charm. It is just 600 meters from Mallory Dock, Mallory Square, and the Ernest Hemingway Home and Museum.
Bahama Village for a Local Experience
Highlights: Blue Heaven Restaurant, Key West Lighthouse, The Key West Butterfly and Nature Conservatory
The small area of Bahama Village is dotted with colorful, quirky buildings and packed full of popular casual restaurants. It has a friendly, informal vibe, and the quaint B&Bs here offer lots of character and cheaper rates than other parts of the city.
If you want to experience Key West like a local, Bahama Village is a good choice. Plus, you’ll be very close to Southernmost Point, and you can be in the center of Old Town within just 15 minutes on foot.
Popular Accommodation in Bahama Village
The Conch House
The Conch House is an 1874 quintessential Grand Key West Estate! As it exists today, it is known as one of the finest examples of ”Conch House” Architecture in Key West. The house encompasses four bedrooms, gorgeous hardwood floors, tall ceilings, incredible millwork, many floor-to-ceiling French doors, original transoms, and tons of natural light.
Plan Your Key West Vacation
Key West blends lively entertainment and nightlife with fascinating historical attractions and laid-back beach culture. A vacation here offers a little something for everyone, which makes it the perfect destination for families and groups of friends.
Now you have a better understanding of Key West’s most popular neighborhoods; you can get started planning your visit to this dynamic region of Florida.
