General Horseplay

Monumental civic building from 1891, restored as a museum for the Key West Art & Historical Society.

Nestled just moments from vibrant Duval Street, this colonial-style retreat boasts airy rooms with ocean views, multiple pools, and a private beach, blending luxury with laid-back Key West vibes.

Revered, longtime eatery offering Caribbean-American cuisine, ocean views & a wine bar.

Sophisticated hotel with airy suites, some with garden views, plus 2 pools & a Japanese eatery. This upscale all-suite hotel is a 3-minute walk from Duval Street's bars and restaurants, and a 5-minute walk from the beach. The contemporary 2-bedroom suites include sleek furnishings, free Wi-Fi, 42-inch flat-screen TVs, DVD players, iPod docks and washer/dryers, plus private balconies or patios, and full kitchens with wine chillers. There are also bi-level units with pool and/or garden views. Freebies include morning muffins and a daily wine hour, as well as smoothies and fruit served poolside. There are 2 heated pools surrounded by tropical gardens, plus a gym. There's also an on-site Japanese restaurant.

Bustling, open-air hangout featuring 2 bars, local seafood & live music on the courtyard stage.

Cozy, homey music venue presenting nightly live jazz with craft beer, cocktails & light snacks.

Nestled on an island accessible only by ferry, Latitudes offers an enchanting dining experience with ocean views, exceptional service, and a contemporary menu that's perfect for special occasions.

Mallory Square is a plaza located in the city of Key West, Florida. It is located on the waterfront in Key West's historic Old Town, adjacent to the cruise ship port. It is located just west of the northern end of Duval Street, facing the Gulf of Mexico. It runs the entire length of Wall Street.

"Simonton Beach"

Guesthouse with low-key rooms & detached conch houses, plus a heated pool & a daily happy hour. This relaxed, art deco-style guesthouse in historic Old Town dates from 1924, and is a mile from The Ernest Hemingway Home and Museum, and a 9-minute walk from Duval Street’s restaurants and bars. Decorated in soft hues, the main guesthouse offers both rooms with en suite bathrooms and rooms with shared facilities. Some provide private porches, and all have free Wi-Fi. Some rooms include flat-screen TVs, microwaves and minifridges. There are also several restored conch houses on the property with rental units, and some have full kitchens. There's a daily complimentary happy hour. Additional amenities include a heated outdoor pool and a hot tub.