The Most Fun Restaurants in the Florida Keys

Most of the fun restaurants in the Florida Keys take influence from its melting pot of cultures and the surrounding Caribbean waters. Indigenous tribes and immigrants from New England, Cuba, and the Bahamas injected their own style into the local abundance of seafood over the years. These influences make much of the local restaurant scene impressive, but where do the savviest foodies choose to enjoy a meal? Welcome to TasteMaker20. OpenTable’s most experienced culinary connoisseurs have provided data and reviews from thousands of restaurants that they just can’t get enough of. Sweet Key West pink shrimp, the local specialty simply referred to as “fish dip,” and a large focus on innumerable dishes created from the mollusk conch are just the beginning of what the area has to offer. Whether foodies crave the abundance of seafood or something a little unique, these fun restaurants in the Florida Keys will keep everyone satisfied. Check out the following fun restaurants in the Florida Keys then book a table that’s equipped with great food and excitement.

The OpenTable Team

18 Restaurants

Updated January 14, 2020

Restaurants:	Ocean Grill & Bar, Little Pearl, Cafe Marquesa…
Price Range:	$$ - $$$$
Cuisines:	Seafood, Contemporary American…
Neighborhoods:	Key West…

Ocean Grill & Bar

$$$$

Seafood

Key West

4.5

728 reviews

There aren’t many eateries that offer breakfast and brunch every day, but Ocean Grill & Bar is one of them. The bottomless Bloody Marys and Mimosas provided during brunch go a long way in making this a fun restaurant in the Florida Keys. Lobster mac 'n' cheese, Shanghai style calamari and smoked salmon bagels make up part of the early offerings, but dinner takes it up a notch with filet mignon, yellowfin tuna, parmesan mahi and lamb osso bucco. Guests should take a moment while eating their meal to enjoy the eclectic lighting, contemporary colors and impressive ocean-focused art that make up the ambiance.

At the moment, there's no online availability within 2.5 hours of your request. Do you have another time in mind?

Little Pearl

$$$$

Seafood

Key West

4.8

2001 reviews

The fun restaurants in the Florida Keys don't have to be in the bustling downtown area, and Little Pearl is evidence of that fact. The outside looks like the quintessential beach diner – basic white, lots of windows and hanging starfish – but the interior pulls off a vintage feel thanks to old-school lighting, planks on the ceiling and traditional beach décor. They have an impressively extensive wine menu, and this goes great with their raw bar and caviar service. Guests also enjoy great selections like sautéed local snapper, magret duck breast, grilled local swordfish and deliciously baked oysters.

At the moment, there's no online availability within 2.5 hours of your request. Do you have another time in mind?

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Cafe Marquesa

$$$$

Contemporary American

Key West

4.8

2183 reviews

The ability to pull off a fine dining atmosphere while maintaining a cozy bar where can friends gather makes Café Marquesa an undeniably fun restaurant in the Florida Keys. Columns, white table cloths, soft lighting and a unique mural that also provides an inside look into the kitchen make the décor quite unique. They focus on contemporary American cuisine that includes local seafood, freshly baked bread desserts and more. Offerings are based on seasonal availability, but the menu has formerly featured shrimp & grits, beef tenderloin, roasted Atlantic swordfish and butter poached spiny lobster.

At the moment, there's no online availability within 2.5 hours of your request. Do you have another time in mind?

Benihana - Key West, FL

$$$$

Seafood

Key West

4.5

1113 reviews

At Benihana, guests get to watch their meals prepared at a communal hibachi grill table before partaking in the offered delicacies. This would be enough to make it one of the most fun restaurants in the Florida Keys, but the gorgeous ocean views, authentic Asian décor and prime location on the beach add even more excitement. Appetizers include options like gyoza dumplings and edamame, but your main dish can be anything from tofu steak or sushi to hibachi steak or the Emperor’s Feast.

At the moment, there's no online availability within 2.5 hours of your request. Do you have another time in mind?

Seven Fish

$$$$

Seafood

Key West

4.6

2257 reviews

Having started out over two decades ago, Seven Fish has earned its place as a Key West classic and one of the fun restaurants in the Florida Keys. The single-story building is white and with long windows – typical of many classic beach town eateries – but the exterior modern art sculptures behind the railings make this place easy to differentiate. Ocean-focused décor, whimsical lighting and unique totems overlooking guests create a distinctive atmosphere. The Thai curry snapper, 7 Fish Meatloaf, banana chicken and daily caught local fish serve as anchors for a fantastic menu.

At the moment, there's no online availability within 2.5 hours of your request. Do you have another time in mind?

La Te Da

$$$$

American

Key West

4.8

1527 reviews

Fine dining is combined with a casual, tropical and open-air atmosphere at La Te Da. Located in the La Te Da Hotel, this fun restaurant in the Florida Keys is immediately recognizable thanks to classic architecture, the poolside dining area and an impressive array of palm trees. Guests inside are treated to beach décor – including a huge hanging mermaid – and live music along with occasional cabaret. For those more interested in food, great selections like shrimp scampi, sautéed Key West yellowtail snapper, baked crab cakes and crispy lacquered duck are offered. Breakfast and brunch are also served.

At the moment, there's no online availability within 2.5 hours of your request. Do you have another time in mind?

Latitudes Key West, FL on Sunset Key

$$$$

Contemporary American

Key West

4.8

11800 reviews

If a meal enjoyed on a secluded island that requires an 8-minute boat ride makes an eatery one of the fun restaurants in the Florida Keys, Latitudes has it covered. Located at Sunset Key Cottages, this dining experience immerses guests in the sea life with waterside dining, gorgeous sunset views and seating among the palm trees. This atmosphere is continued inside with wall-mounted sea beasts and a country club setting. Guests enjoy great options like seared grouper, seafood pasta, lobster tail and dry aged strip steak after the Lil Princess ferry arrives at the island.

At the moment, there's no online availability within 2.5 hours of your request. Do you have another time in mind?

Tavern N' Town - Marriott Key West

$$$$

American

Key West

4.6

1756 reviews

Located in the Marriot Beachside Hotel, Tavern N’ Town looks explicitly fine dining while maintaining its fun appeal by showing sporting events throughout the eatery. The lighting, bar and even seating scream ‘high class’ and classic, and this remains true in the nearby den where guests can take a load off before splurging. The menu offers amazing cuisine such as calamari, filet mignon, seared yellowfin tuna and even a selection of pizzas. If this wasn't enough, the Tapas Theater Kitchen closes the deal on making this one of the most fun restaurants in the Florida Keys.

At the moment, there's no online availability within 2.5 hours of your request. Do you have another time in mind?

Azur

$$$$

Mediterranean

Key West

4.8

2119 reviews

Mediterranean cuisine can be found in old Key West thanks to Azur Restaurant. Guests are able to easily walk to the eatery from most guest houses and hotels, and once they arrive, they’re privy to a fine dining experience complete with contemporary lighting, plenty of foliage and even beautiful views of stone fountains. Early risers should enjoy the brunch, but those who arrive later in the day are treated to options like chilled octopus, beef carpaccio, confit duck leg and delectable lamb chops.

At the moment, there's no online availability within 2.5 hours of your request. Do you have another time in mind?

Florida Keys Steak & Lobster House

$$$$

Seafood

Marathon

4.7

1749 reviews

When surf and turf combine with a fun restaurant in the Florida Keys, the Florida Keys Steak & Lobster House is the undeniable result. The atmosphere brings together fine dining and casual, and this ends with luxurious dining sets being surrounded by unique art, bubble tanks and strange fish hung on the walls. The bar offers an even more relaxed atmosphere, and the Mahi Mahi, filet mignon, cowboy steak and several types of lobster tail can be enjoyed regardless of where patrons sit. Guests can even bring in their own catch of the day to have prepared!

At the moment, there's no online availability within 2.5 hours of your request. Do you have another time in mind?

La Trattoria Oceanside

$$$$

Italian

Key West

4.6

1631 reviews

Specialty desserts, a gorgeous oceanside view and one of the happiest Happy Hours in the area make La Trattoria Oceanside an impressive contender for the most fun restaurant in the Florida Keys. One look on the inside – which reveals fine linen tablecloths, classic seating, overhanging foliage and a variety of artwork – gives off an undeniably luxurious vibe. Martini Mondays, however, showcase a willingness to let loose. Menu offerings include Italian favorites like lasagna bolognese, tortellini alla Romana, ravioli trattoria and braised veal shank.

At the moment, there's no online availability within 2.5 hours of your request. Do you have another time in mind?

Castaway Waterfront Restaurant & Sushi Bar

$$$$

Seafood

Marathon

4.6

1171 reviews

The 1950s were about as cool as any decade could get. This makes it no surprise that Castaway Waterfront Restaurant & Sushi Bar – founded in 1951 – is one of the fun restaurants in the Florida Keys. The eatery was remodeled in 2007, so new ocean-focused décor and big-screen televisions combine with vintage design and classic wall ornamentation. Patrons are treated to a raw bar and delectable menu options like snapper BLT, fish tacos, sautéed gator and chicken enchiladas. Breakfast, lunch and vegetarian options are also available.

At the moment, there's no online availability within 2.5 hours of your request. Do you have another time in mind?

First Flight Island Restaurant & Brewery

$$$$

Seafood

Key West

4.5

926 reviews

Located in Pan American's home office and situated under two Strangler Figs, the First Flight Island Restaurant & Brewery offers a unique dining experience. History lovers will enjoy the fact that this is where the first international plane ticket was purchased, but everyone will appreciate the impressive Happy Hour menu. Popular menu items include fish tacos, organic chicken, filet mignon and mutton snapper. These are excitedly consumed surrounded by vintage décor, design based on air travel and unique dining sets that can’t be found anywhere else.

At the moment, there's no online availability within 2.5 hours of your request. Do you have another time in mind?

Pierre's Restaurant & Lounge

$$$$

Contemporary French / American

Islamorada

4.7

974 reviews

If visitors find themselves on a palm-lined beach overlooking some of the most beautiful blue water, there's a good chance they may stumble upon Pierre's Restaurant & Lounge. It's located in a plantation-style house that's difficult to miss, and guests can enjoy their meals out on its veranda. The interior is just as impressive - with nautical decor, vintage art and ornate entryways – but the menu does well at outshining all of this. Offerings include king crab ceviche, grilled Denver lamb chop, Florida lobster curry and Mediterranean Branzino.

At the moment, there's no online availability within 2.5 hours of your request. Do you have another time in mind?

DiGiorgio's Cafe Largo

$$$$

Italian

Key Largo

4.3

800 reviews

Anyone seeking a fun restaurant in the Florida Keys that offers an authentic Italian experience simply can’t miss DiGiorgio’s Café Largo. Featured on 'Diners, Drive Ins and Dives’, this eatery’s menu is popular across the country. Offerings include veal marsala, New York strip, seafood linguini marinara and cheese ravioli. Those seeking the dish featured on the popular television show should opt for the veal chop cutlet Florentine. Old-world paintings, simple dining sets, international flair and an abundance of wine make guests feel like they’re really in Italy.

At the moment, there's no online availability within 2.5 hours of your request. Do you have another time in mind?

Nine One Five

$$$$

Contemporary American

Key West

4.6

3305 reviews

A Victorian home from the 1850s houses the popular Nine One Five restaurant. History buffs will understand that this already means it’s one of the most fun restaurants in the Florida Keys, but there’s really a little something for everyone to love. The interior has contemporary flair – including quirky seating options – but the architecture and soul of the eatery remains vintage. There’s an impressive drink menu – featuring just about any wine one could envision – and the culinary offerings include chipotle pork tacos, lobster ravioli, yellowtail snapper and grass-fed burgers.

At the moment, there's no online availability within 2.5 hours of your request. Do you have another time in mind?

Martin's

$$$$

European

Key West

4.6

1281 reviews

Foodies who enjoy a bit of variety in their meals should check out Martin’s. By combining tropical with classic in every aspect of its operation, the eatery is consistently viewed as one of the fun restaurants in the Florida Keys. Beach foliage meets fine art, and veiled partitions meet eclectic lighting. The menu manages to keep this mashup going by offering choices such as shrimp fettuccine alfredo and filet mignon while also granting lovers of Jager schnitzel and yellowtail capri their desires.

At the moment, there's no online availability within 2.5 hours of your request. Do you have another time in mind?

Hard Rock Cafe - Key West

$$$$

American

Key West

4.2

310 reviews

No list of fun restaurants in the Florida Keys – or anywhere for that matter – would be complete without mentioning the Hard Rock Café. Adding to the excitement is that this location is inside an allegedly haunted Victorian-style house, and since they maintained the vintage appearance on the inside, it’s unlike any other Hard Rock Café out there. The menu is what one would expect from any of the franchised locations, and it includes Legendary® steak burgers, Twisted Mac Chicken & Cheese, grilled Norwegian salmon and the popular hot fudge mini-milkshake.

At the moment, there's no online availability within 2.5 hours of your request. Do you have another time in mind?

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The Most Fun Restaurants