Pier House Resort & Spa

The location – on a quiet stretch of beach at the foot of Duval – is ideal as a buffer from and gateway to the action. Its sprawling complex of weathered gray buildings includes an original Conch house.

It's fair to say that no hostelry is more 'front and center' hereabouts than this former pineapple factory, which helped put Key West on the map as a vacation destination upon opening in 1968, provided a hangout for the likes of Truman Capote, and helped launch careers like those of treasure hunter Mel Fisher, chef Norman van Aken, Bob Marley, and Parrothead-in-Chief Jimmy Buffett. Besides location, it offers good service and 6 acres' worth of bells and whistles including a sweet little beach and the island's largest, most comprehensive spa.

Located at the furthest end of Duval Street, this hotel has been a staple in Key West since the 1960s. The hotel features an upscale tropical decor and lush landscaped grounds in a superb location.

Six low-rise buildings, tucked into bougainvillea gardens between the harborfront and the historic Old Town, house 142 guest rooms and suites. The luxury resort maintains an authentic Old Key West attitude with help from local art and the Chart Room Bar, which continues to serve free popcorn and steers clear of any neon slushie drinks.

A full-service, four-pearl hotel in a town filled with B&Bs, this property differentiates itself from the competition by providing more rooms and more amenities – including an on-site spa, pool, restaurant/bar, and beach access – in a convenient downtown location. Rooms are simple and comfy with premium bedding, rain-style showers, flat-screen TVs, mini-fridges, and free Wi-Fi.