Best Places To Stay In Key West

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This free-spirited town, the southernmost point in the continental United States, is a magnet for visitors with varying interests—whether it’s the lively party scene, the rich, literary history or the crystalline waters for sailing, fishing and snorkeling. Fortunately, there are plenty of hotels in Key West to accommodate all of those interests, from cozy B&Bs in the center of town to waterfront resorts with marinas.

Casa Marina Key West, A Waldorf Astoria Resort

First opened on New Year’s Eve in 1920, this gracious resort listed on the National Register for Historic Places has been welcoming guests for generations for its serenity away from all the activity in town. (But it’s just steps away from town for those who want to venture back in.) Part of that attraction is its beach: 1100 feet of beach reserved exclusively for hotel guests and the perfect launch point for kayaking or snorkeling the barrier reef. The 311 rooms are contemporary in feel, recently refreshed after a $42 million renovation, and other facilities include a spa and two outdoor pools. 

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Oceans Edge Key West Resort Hotel & Marina

Another destination for guests who want to be near the water, this 175-room resort is located on 20 acres on Stock Island, the small island attached to and just north of Key West; all of the spacious, crisply decorated rooms have terraces with water views as well. There’s also a 165-slip marina with boats on call for fishing and sailing/motor charters, plus six outdoor pools for those who want to relax on the grounds. And a regular shuttle operates to and from downtown Key West for those who don’t want to negotiate the limited parking in town.

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The Perry Hotel Key West

Also on Stock Island, this contemporary 100-room hotel fronts another marina with 220 slips and charters available for fishing, snorkeling and scuba diving. Fishing artifacts in the resort’s common rooms are both interesting design touches and reflections of the island’s commercial fishing industry. But the hotel itself is a sophisticated, romantic enclave within this working community. There’s also an excellent restaurant on site: Matt’s Stock Island Kitchen & Bar, serving creative seafood dishes. And for those who want to leave their cars behind when going into downtown Key West, the hotel also operates a regular shuttle.

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Sunset Key Cottages

Along the water, but closer to downtown, this 27-acre island (just 500 feet from the activity in downtown Key West) houses 40 cottages, ranging from one to four bedrooms decorated in tropical style and surrounded by bougainvillea and orchids. The cottages are designed to be residential, with full kitchens, and food items are pre-stocked. Popular with families due to the range of amenities and activities, from the secluded white sand beach to tennis courts, fishing and snorkeling charters, sailing and parasailing, many never leave the resort. But those wishing to go into Key West can easily take the resort’s private ferry.

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The Marquesa Hotel

One of the Victorian “conch” houses in the city—including a new 14-room extension called Marquesa 4-1-4—this intimate hotel regularly tops readers’ lists of the best places to stay in Key West. Polished wood floors, antiques (or very good reproductions), bold fabrics, and fourposter beds (especially in the Bahama Suites in the new extension) add up to atmosphere. The convenient location—one block to Duval Street—serene back garden with a pool and a destination restaurant, Café Marquesa, make this hotel popular with visitors and locals alike.

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H2O Suites

Another intimate hotel within Old Town Key West, this all-suite hotel features sophisticated décor and balconies or patios for lounging. The rooftop pool is a top people-watching spot, too, as are the private plunge pools attached to deluxe suites. There’s also a light-dining menu by the pool; for a more substantial Japanese menu (sushi, teriyaki, tempura) guests go over to the hotel’s sibling Santa Maria Suites, which features two bedroom suites. But the concierge is especially well connected and can suggest and then get guests into some of the more popular restaurants in town.

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