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Three-and-a-half hours after leaving Miami, the Overseas Highway delivers one of America’s most rewarding arrivals. The turquoise water gets brighter as you go, and by the time you see Mile Marker 0, you’ve officially reached the end of the road.
From there, where you stay can shape the entire trip. Fortunately, Key West has a hotel for nearly every travel style. Historic hideaways sit a short stroll from Duval Street, waterfront resorts put boat traffic front and center, and sprawling properties offer enough pools, restaurants and amenities that you may never want to leave. These are the 11 best hotels in Key West, listed alphabetically, for travelers planning that next island escape without having to hop on an international flight.
Provided by Blue Flamingo Resort
Blue Flamingo Resort Key West
One of Key West’s newest resorts, Blue Flamingo Resort greets visitors just as they roll onto the island. Its colorful design, 245 guest rooms and pair of expansive pools create a vacation atmosphere from the moment you check in. The Backyard Pool & Social Club keeps the action going with bocce, shuffleboard, cornhole, giant Jenga and poolside cocktails from Toasted Coconut and Rum Row. 3820 N. Roosevelt Blvd., Key West; 305-320-0940; blueflamingokeywest.com.
Casa Marina Key West
Few resorts carry the history of Casa Marina. Originally envisioned by railroad magnate Henry Flagler, the landmark property has welcomed guests for generations while maintaining its unmistakable Old Key West character. A private beach, elegant public spaces and architecture tied to some of America’s most celebrated designers give the resort a truly unique sense of place. 1500 Reynolds St., Key West; 305-296-3535; casamarinaresort.com.
Eden House Resort
Built in the 1920s as the Gibson Hotel, Eden House remains one of Key West’s longtime boutique favorites. The property embraces its history while adding thoughtful sustainability efforts that have earned certification as a Key West Green Hotel. Fans of Hollywood trivia can also appreciate that scenes from the Goldie Hawn film “Criss Cross” were filmed here. 1015 Fleming St., Key West; 786-761-9599; edenhousekw.com.
Provided by Havana Cabana
Havana Cabana
Pre-Revolution Cuban culture is the inspiration throughout Havana Cabana, where vintage automobiles, hand-rolled cigars and lively music immediately set the mood. The resort surrounds what it bills as the largest pool in Key West, creating an inviting centerpiece for long afternoons under the Florida sun. Complimentary transportation in a classic Chevy adds another memorable touch, while Vespas and bicycles make exploring Old Town a breeze (literally). 3240 N. Roosevelt Blvd., Key West; 305-294-5541; havanacabanakeywesthotel.com.
Hilton Key West Resort & Marina
Hilton’s newest Key West resort expands the brand’s footprint with a marina-front setting on Stock Island. The 175-room property pairs spacious accommodations, many overlooking the Atlantic, with six saltwater pools, island-inspired dining and direct access to boating and fishing adventures. Complimentary shuttles simplify trips into Old Town while paddleboards, kayaks, yoga classes and poolside movie nights keep guests entertained between excursions. 5950 Peninsular Ave., Key West; 786-862-6300; hilton.com.
La Concha Key West
Few hotels put you closer to the pulse of Key West than La Concha. Right on Duval Street, this longtime landmark makes it easy to spend your days hopping between renowned bars, restaurants, boutiques and galleries without ever needing a car. Despite its central location, the hotel still offers a comfortable retreat after hours of exploring Old Town. 430 Duval St., Key West; 305-296-2991; laconchakeywest.com.
Ocean Key Resort & Spa
Sitting at the very end of Duval Street, Ocean Key Resort & Spa enjoys one of the island’s most recognizable locations. Guest rooms blend tropical style with colorful Key West character, and many overlook the Atlantic, historic Old Town, or the famed Sunset Pier. The waterfront landmark draws visitors nightly for live entertainment, tropical cocktails and one of the best sunset views on the island. 0 Duval St., Key West; 305-809-8072; oceankey.com.
Provided by The Marker
The Marker Key West Harbor Resort
Hidden beside the Key West Historic Seaport, The Marker offers a peaceful home base within easy walking distance of Duval Street and Mallory Square. The waterfront resort features three pools surrounded by lush tropical landscaping, spacious guest rooms with private balconies and an open-air restaurant perfect for dining outdoors. Its name references the final U.S. 1 mile marker, celebrating the relief of reaching the end of the road. 200 William St., Key West; 305-501-5193; markerkeywest.com.
The Perry Hotel & Marina Key West
The Perry has earned a loyal following thanks to attentive service, a Michelin Key and its setting beside the largest wet-slip marina in the Florida Keys. Fishing boats and luxury yachts provide the backdrop from the waterfront pool, while Salty Oyster keeps guests nourished between swims. Complimentary hourly shuttle service makes it easy to reach the Historic Seaport and Old Town before returning to the quieter side of Key West for the evening. 7001 Shrimp Rd., Key West; 877-496-8712; perrykeywest.com.
The Reach Key West
The Reach recently introduced the island’s only all-inclusive vacation package, giving guests breakfast, lunch, dinner and unlimited drinks for one daily price ($310). The resort also sits on Key West’s only private natural sand beach, making it a favorite for swimming, sailing, snorkeling and scuba diving. Duval Street, the Southernmost Point and the Ernest Hemingway Home and Museum are all within easy walking distance. 1435 Simonton St., Key West; 305-296-5000; hilton.com
Southernmost Beach Resort
Occupying six oceanfront acres where Old Town meets the Atlantic, Southernmost Beach Resort makes it almost too easy to settle into island life. Guests can rotate between three heated pools, two beaches, four bars, a full-service spa, oceanfront dining and accommodations ranging from restored Victorian homes to mid-century favorites. The Southernmost Point buoy sits just outside the resort, placing one of Key West’s signature selfie stops only steps away. 1319 Duval St., Key West; 305-296-6577; southernmostbeachresort.com.
