Truly an original, the waterfront Pier House Resort & Spa has attracted eclectic artists for years. In the 1960’s, Jimmy Buffett played his first Key West gig at the hotel’s funky Chart Room Bar. Get lost in the views of the crystal-blue sea or walk to the many watering holes that line lively Duval Street; 1 Duval St., 305-296-4600.
Perfect for the young and hip (of any age), The Gates Hotel is a new hotspot with a laid-back-meets-retro flair. Channel Hemingway at the hotel’s Rum Row Poolside Bar, selecting from a fine selection of Prohibition era cocktails created in partnership with the Key West First Legal Rum Distillery; 3824 N. Roosevelt Blvd., 305-320-0930.
If sweet serenity is what you’re after, then head to the six-acre Southernmost Beach Resort and kick back in one of the oceanfront hammocks, relax on the beach, or stroll two short blocks to the iconic concrete buoy at the Southernmost Point; 508 South St., 800-354-4455.
Situated directly on the Key West Harbor and next to Mallory Square, Ocean Key Resort & Spa, A Noble House Resort offers panoramic water views that span for miles. At the hotel’s Sunset Pier, pull up a front row seat to famed nightly sunset celebrations, complete with live music and plenty of local entertainment; 0 Duval St., 800-328-9815.
Escape to the secluded, 27-acre island of Sunset Key where you’ll find Victorian-style cottages nestled on a private, white-sand beach. Only accessible by boat and located just seven minutes from the mainland, Sunset Key Cottages, a Luxury Collection Resort feels like it’s a world away from the bustling bar scene; 245 Front St., 305-292-5300.
Located in the heart of all the action on Duval Street, La Concha Hotel & Spa is a Key West icon dating back to 1926. Detox from late revelry and take in stunning city and ocean views at the hotel’s rooftop spa, the highest point on the island; 430 Duval St., 305-296-2991.
One of the best beachfront hotels in Key West, The Reach, A Waldorf Astoria Resort offers an impressive shoreline sanctuary. Partake in a variety of water sports and wander out onto the private pier to watch for dolphins; 1435 Simonton St., 305-296-5000.
Situated on the waterfront, The Marker Key West is a boutique hotel with a free-spirit ambience that seafarers and adventurers will adore. Set sail on a sunset cruise or walk to the many saloons and taverns along Duval Street; 200 William St., 855-485-9291.
A beachfront hotel landmark conceived by railroad tycoon Henry Flagler, Casa Marina, A Waldorf Astoria Resort dates back to the glamorous 1920s. Soak up elegance and grandeur that has attracted the likes of dignitaries and the crème de la crème for nearly a century, not to mention a stunningly redone lobby, two great pools, and a lovely beach; 1500 Reynolds St., 305-296-3535.
A great spot for families, Margaritaville Key West Resort & Marina offers everything you’d expect from a waterfront gem, including a lushly landscaped pool area and a marina with easy access to boating excursions like fishing and snorkeling tours. 245 Front St., 305-294-4000.