The Grand Guesthouse Key West Florida Dining


Staff’s Top Picks

We’ve listed some of our favorite restaurants and hope that you will enjoy them.  We will be happy to help you make any reservations you need, just let us know!  Enjoy!!



 A and B LobsterHouse        Seafood, Steak

700 Front St., upstairs; (305) 294-5880           

Since 1947, A&B (named for its original owners, Alonzo and Berlin) has been a destination of choice for superior seafood dining with great views of the boats docked at Key West Bight. Try the shrimp cocktail martini appetizer: jumbo Key West pink shrimp served chilled with horseradish cocktail sauce and lemon.  $$$


 Ambrosia Japanese Restaurant

1401 Simonton St.; (305)293-0304     

Ambrosia serves up fresh sushi and Japanese-influenced fare. Try the sashimi appetizer with four varieties of the day’s fresh fish, or the duck tataki: duck breast marinated in sweet miso paste, seared, sliced thin and served with spicy green yuzu pepper. $$$


Azur Key West             Mediterranean, New American

425 Grinnell St.; (305) 292- 2987     

Enjoy Azur’s Mediterranean fare on a shaded terrace by a waterfall or in the comfort of the cool dining room. The menu changes seasonally. Highlights include the eggplant chips topped with salt and rosemary honey, and the whole, grilled branzino fish served with rosemary, garlic, cured tomatoes, Kalamata olives and Yukon potatoes. $$$


Better Than Sex: A Dessert Restaurant

926 Simonton St.; (305) 296-8102     

This decidedly adult dessert-only restaurant serves tongue-in-cheek titles of its sweet confections, such as the Fork You Fondue: vanilla cheesecake fondue served chilled and paired with pound- cake doughnut holes rolled in cinnamon sugar. $$


Bistro 245                         Traditional American

The Westin Key West Resort, 245 Front St.; (305) 292-4320

Dine indoors or outside with sweeping views of Key West Harbor perfect for viewing the sunset. Bistro 245 serves fresh island cuisine such as grilled pineapple salad, gazpacho, shrimp bisque or herb-seared local mahi-mahi, served with tangerine butter, scallion potato cake and grilled asparagus. $$$


 Blue Heaven                   Floribbean

729 Thomas St.; (305) 296-8666              

In historic Bahama Village Blue Heaven is one of the more casual Key West restaurants, with live entertainment and American, Caribbean and vegetarian cuisine. Try the popular Key lime pie (Kenny Chesney is a fan). $$$


B.O.’s Fishwagon            Burgers, Seafood

801 Caroline St.; (305) 294-9272

Home of the “Square Grouper Sandwich,” B.O.’s Fishwagon is a slice of old Key West. Stop by Friday nights for great live music and try the fried cracked conch, shrimp or fish-of- the-day sandwich. Try a fried seafood platter, served with black beans and rice, salad and hand-cut fries. $$


Boathouse Bar & Grill        Seafood, Traditional American

700 Front St.; (305) 294-9191

The Boathouse, on the harbor, is a favorite happy-hour spot, serving half-priced beers and appetizers. Try the Boathouse bread or the lobster tail tempura, served with a chili mango sauce. $$


Commodore Restaurant             Seafood, Traditional American

700 Front St.; (305) 294- 9191                

Request a table by the window for fine dining with great views of Key West Bight. The Commodore serves select seafood and steak dishes as well as an extensive wine menu. Try the mahi-mahi sautéed with mushrooms, tomatoes, capers and lemon in a white wine sauce, served with roasted red potatoes.  $$$


Deuce’s Off The Hook            Greek, New American, Seafood

728 Simonton St.; (305) 414-8428      

This bistro-style seafood grill serves fresh local catch in addition to some classics. Try out its popular American turkey dinner, The Gobbler: roasted turkey served over bacon mashed-potatoes with sage stuffing, all on a waffle topped with rosemary gravy, or the Greek spanakopita. They also have wine from around the world and craft beer on tap and in bottles. $$


D.J.’s Clam Shack                    Sandwiches, Seafood

629 Duval St.; (305) 294-0102;             

Recently featured on the Food Network, D.J.’s Clam Shack serves traditional Northern and Southern American seafood. Favorites include the overstuffed Maine lobster roll, cracked conch tacos, New England clam chowder, and golden-fried clam strips served with fries or coleslaw. $$


El Siboney Restaurant                   Cuban

900 Catherine St.; (305) 296-4184;            

El Siboney is one of the island’s best Cuban restaurants, serving generous portions of affordable, traditional Cuban cuisine. Favorite menu items include the café con leche, Cuban mix sandwich and the roast pork with yellow rice, black beans, sweet plantains and Cuban bread. $$


Flaming Buoy Filet Co.                  Caribbean, New American, Seafood

1100 Packer St.; (305) 295-7970;            

This restaurant and wine bar serves inventive contemporary menu options such as barbecued Danish baby back ribs, which are spice-rubbed and slow- baked, then finished on the grill with a jalapeño barbecue sauce and served with sweet-and-spicy Szechuan green beans and macaroni and cheese. $$$


Garbo’s Grill          Seafood, Burgers, Food Truck

409 Caroline St.; (305) 304- 3004

Garbo’s Grill isn’t your typical brick-and-mortar restaurant. It’s a food truck that was recently featured on the Food Network. Locals Eli and Kenna Pancamo serve popular dishes such as Korean barbecue tacos: marinated beef short rib, Napa cabbage, scallions, carrots, daikon, citrus soy dressing and siracha served on two soft tortillas. $


Hogfish Bar & Grill          Seafood

6810 Front St., Stock Island; (305) 293-4041              

This is the place for local seafood, with Key West pink shrimp, lobster and hogfish. The restaurant only uses hogfish caught by local divers and does not substitute other fish when it’s out, so call ahead to make sure the hogfish is available. Try the fried hogfish sandwich with Swiss cheese, onions and mushrooms on fresh Cuban bread. $$


 Hog’s Breath Saloon           Traditional American

400 Front St.; (305) 296- 4222           

Hog’s Breath has great seafood, fresh smoked barbecue, live music and even a kid’s menu.  Sit inside or outside on the spacious patio while enjoying the live, local entertainers. Try the seafood sampler: peel-and-eat shrimp, conch fritters, garlic shrimp dip and smoked fish dip served with coleslaw, lemon, dipping sauces and crackers. $$


Hot Tin Roof                Latin American, Seafood

Ocean Key Resort & Spa, 0 Duval St.; (305) 296-7701         

The Hot Tin Roof restaurant is at the Ocean Key Resort & Spa overlooking Key West Harbor. Request a table on the covered patio at sunset to catch some of the best views on the island. Try the shrimp tacos, served with warm tortillas, pico de gallo, queso blanco and salsa verde. $$$


Latitudes Beach Restaurant              New American

Sunset Key (shortferry ride from Westin Resort,245 Front St.); (305) 292-5394

Request a table outside near the water for an uninterrupted view of the sun as it sets over the Gulf of Mexico. When the stars come out, tiki torches illuminate the beachfront. Try the pan-seared snapper served with citrus risotto, asparagus, ginger-lime cream sauce, tropical fruit relish and crispy plantains. $$$


Nine One Five and Point5               New American

915 Duval St.; (305) 296-0669          

Dine al fresco with ample views of Duval Street on the elegant Victorian-style patio, sit indoors on the first floor amid eclectic artwork, or head upstairs to Point5 on the second-floor balcony. Point5 serves light bites and craft cocktails, while nine one five serves contemporary American cuisine infused with global flavors. $$$


Prime Steakhouse (also seafood)

951 Caroline St.; (305) 296-4000

Quality, prime aged beef—such as New York strip—is the focus of Prime Steakhouse, but lobster tail, oysters, fresh local catch and pork tenderloin are also on the menu. Start with the she-crab soup followed by the Surf & Turf: a 10-ounce fillet mignon and 8-ounce Florida lobster tail served with oven-roasted garlic and a red wine demi- glace. $$$


The Salty Angler               Barbecue, Seafood

1114 Duval St.; (305) 741-7071

The Salty Angler promises a casual atmosphere where fishing stories are as key as the adult milkshakes, like the Dirty Thin Mint or the SomBeach. Try out Thunder Thighs, smoked for two days in spicy brine and slow-smoked over hickory, or the Local’s Catch, with jalapeño cornbread or toasted brioche bread. $$


Salute! On the Beach               Caribbean, Italian, Seafood

1000 Atlantic Blvd.; (305) 292- 1117;                

Right on Higgs Beach, Salute serves Italian cuisine with lighter, Caribbean-influenced takes on classics, with fresh breads, vegetables and local seafood. Request a table overlooking the beach and try the sautéed scallops on fresh greens served with tropical salsa. If you’ve got the kids with you, there’s a public playground right next door. $$


Santiago’s Bodega                     Spanish, Tapas

207 Petronia St.; (305) 296-7691         

This tapas-style restaurant, a local favorite, is off the beaten path, deep in Bahama Village. Choose from more than 30 inventive tapas-style dishes, soups and salads, and don’t miss the hot rum-soaked bread pudding for dessert. Tables typically fill up quickly, so reservations are recommended. $$


Schooner Wharf Bar                    Traditional American, Seafood

202 William St.; (305) 292- 3302                  

This open-air bar and restaurant is a slice of old, funky Key West that serves breakfast, lunch and dinner with a unique blend of special events and great live music at the water’s edge. Conch fritters, smoked fish dip and chowders are on the menu, as well as a variety of soups, salads and sandwiches. $$


Seven Fish Restaurant           Seafood, New American

921 Truman Ave.; (305) 296- 2777                

This intimate seafood- centric restaurant features “off-beat, yet elegant architecture and tastefully accessorized space.” In addition to fresh fish, the menu includes grilled banana chicken, New York strip steak, meatloaf with mashed potatoes, and sea scallops served over mashed potatoes, pea purée and spinach. Reservations recommended. $$$


The Waterfront Brewery             Seafood, Traditional American

201 William St.; (305) 440-2270                

Stop in to try the beers of the Florida Keys and stay for the beer- battered fish and chips, slow-roasted baby back ribs or chargrilled ribeye. Make sure to get a table by the water, as the sunset views over the harbor are fantastic. $$