El Meson de Pepe

El Meson de Pepe's is a family owned and operated Cuban Restaurant here in Key West for over 20 years. Chef Pepe Diaz and family first opened in 1984, bringing locals and tourists alike delicious Cuban favorites. El Meson de Pepe is dedicated to great quality food and the preservation of Cuban-Conch Heritage in Key West. Live music nightly.

Grand Cafe Key West, Inc.

The Grand Cafe is a warm and inviting family owned restaurant in Key West. Located in a breathtaking victorian mansion, The Grand Cafe serves fine wines, perfect martinis, and of course delicious seafood and meats. You are invited to spend a lazy afternoon having lunch in our garden, take your time with starlit meals on our wraparound porch, and enjoy our newly renovated bar and lounge.

Hard Rock Cafe
Coming Soon!

Island House

Private, clothing-optional resort for men in Old Town Key West. Poolside café and bar. Luxury rooms with our feather topped beds. Heated pool, fully-equipped gym, sauna, steam room, two Jacuzzis, and a tanning deck with misting fans. We were recently named “The best gay men's resort in the world” by OUT Traveler magazine. All facilities of the Island House are open and available 24 hours every day. Men welcome at the restaurant and bar anytime. Daily and 12 visit resort passes are available for locals and men staying elsewhere. Inquire at the front desk.

Kelly's Caribbean Bar/Grill
Kelly's Caribbean is one of Key West's most impressive and historic buildings. The birthplace of Pan American Airlines! In the main restaurant garden soaring trees arch and create a living canopy with sparkling and twinkling lights at night. Kelly's is also home to the first micro-brewery in the key's and home to the Southernmost Brewery in the USA! Don't miss a visit to the famous Crash Bar. The second floor rooftop garden is the perfect spot for an intimate wedding reception, corporate party or and special event get-togethers. Catering & special event information is available at www.AKeyWestAffair.com.

Margaritaville Cafe & Store
Margaritaville Key West is just the kind of place you’d expect to be cruising home from when you “blew out your flip flop and stepped on a pop-top.” The restaurant & store are located on popular Duval Street in the town that is the real deal escape for artists, writers, musicians and anyone needing to kick back for awhile. Guests looking to escape from mundane and expected restaurants can have an authentic Key West experience here. Groups up to 200 people can make Margaritaville their own tropical paradise and give your group an island adventure they won’t forget.

Pier House Resort and Caribbean Spa

If you’re seeking an authentic taste of “Key West” you will find it at Pier House Resort and Caribbean Spa. We offer our guests a collection of accommodations that create an atmosphere that is distinctively Key West. Acknowledging our long standing reputation as Key West’s authentic island resort, our guest rooms reflect a relaxed graciousness found in Caribbean’s traditional island style. Our resort is located at the corner of the Gulf of Mexico and Duval Street. Beautiful tropical gardens surround our pool and open directly onto the private beach.

Sloppy Joe's

Sloppy Joe's is one of the most famous bars in Key West. Located at the corner of Greene and Duval Streets since 1937, it’s filled with historical memorabilia of days gone by, and boasts of times when Hemingway made Key West home. The atmosphere is casual and relaxed. Sloppy Joe's is known for generous drinks, quality food, live entertainment and world-famous t-shirts. Joe's Tap Room "features crafted beers on tap," the same food/drink menu and has big screen satellite TV.

Sunset Watersports

Sunset Watersports is Key West's oldest and largest Water Sports company with 4 locations since 1984. Offers: Parasail $29 AM flights, Reef Snorkel Trips $35, Sunset Cruises $30, 2 Beach Locations offering Sailboats, Kayaking, Wind Surfing, Chairs & Umbrellas, Safari Tours & Boat Rentals. The World's 1st Water Sports Party Boat Company introduces our NEW 2 Million Dollar Air-Conditioned 149 Passenger Party Cat. More on Sunset Watersports >

The Westin Key West Resort & Marina

The Westin Key West Resort & Marina is ideally located on the waterfront in Old Town, within walking distance of attractions, restaurants, shopping and vibrant nightlife. The resort offers multiple dining venues, marina vendors with a variety of water sport activities and a nightly Sunset Celebration on the pier making The Westin Key West Resort & Marina as desirable a location as Key West itself.