22 Best Cocktail Bars in Key West

Milagro Restaurant and Bar Bar • $$$
1401 Simonton St, Key West

Customers` Favorites

Stacked Blue Corn Enchiladas
Rosemary Roasted Prime Rib
Classic French Onion
El Corazon Margarita
Wood Grilled Octopus
Mashed Potatoes
Bread Pudding
Key Lime Tart
Creme Brulee
Caesar Salad

“The food is awesome. We had octopus and calamari as a starter which was already filling. As a main course, filet mignon and fettucine. Both super tasty and great quality. Last but not least, the key lime tart. But there was absolutely nothing to complain about. We decided to make a reservation at very short notice and only got a seat at the counter, but it was super comfortable. Sylvia our bar tender was super super friendly and served excellently. A more than successful evening with an excellent meal. Danger! Very modern and not Key West style. If you're looking for something like that, you shouldn't go here, but if you're looking for great quality, this is the place for you.“

4.6 Superb337 Reviews
The Rum Bar Bar • $
1117 Duval St, Key West

Customers` Favorites

Try Our Rum Flights Five Samples of Premium Aged Rums
Toasted Coconut Rum Bar
Killer Redhead
Banana Split
Guava Breeze
Rum Tasting

“A great selection of rums from many distilleries around the world. As a rum snob, I prefer my rum to taste like rum, not whiskey. If you are the same, then be sure to express that. Otherwise, this is a great little place for getting your rum fix.“

4.7 Superb104 Reviews
Heroes Bar and Liberty Lounge Sports Bar • $
506 Southard St, Key West

“Most friendly bar in Key West. Right away we became family with the bartender and fellow patrons that were drinking. Very cool place and every cooler people there. We were recommended by a local in Tavernier and so glad we went! Also very good food next door!“

4.9 Superb57 Reviews
The Roost Cocktail Bar • $$
508 Fleming St, Key West

“We absolutely loved this place ! We had espresso martinis that were one of the best I’ve had. My husband also got their Maria-Rita , which was truly the best we had in the keys- great taste and very clearly made in-house (not your basic mixers). Would recommend !“

4.5 Superb77 Reviews
Bel Mare Restaurant Fine Dining • $$$
700 Front St, Key West

Customers` Favorites

Scallops & Pork Belly
Chocolate Temptation
Shrimp Orecchiette
Key Lime Desert
Lobster Scampi
Veal Bolognese
Chef's Ceviche
Key Lime Pie
Kale Salad
Octopus

“My husband and I went here after our wedding, and it definitely was the fancy celebratory restaurant we were looking for. We got a free dessert and the service was amazing. Our waiter was really responsive and friendly and knew the menu really well. The interior is incredible and has all the nautical vibes you might expect from a restaurant right by the sea. Everything felt so fancy. Okay the food. The food may be pricy, but it’s SOOOO worth it!! I had the Shrimp Orecchiette and it changed my life. The shrimp is clearly VERY fresh and different from anything you might get at a store or at a standard seafood restaurant. The pesto was also the best pesto I’ve ever had. My husband really enjoyed his food too. Overall, I’d recommend this restaurant to everyone, as long as you’re willing to spend $100+ for two people.“

4.3 Superb262 Reviews
Follow The Rabbit Bar Bar • $$
404 Southard St, Key West

“Always fantastic. I usually get the steak which is excellent but last night I ordered the eggplant dish. It was really tasty. Portions are large! Service is always friendly and attentive. Definitely a favorite spot of ours and we live in town. Would highly recommend.“

4.4 Superb99 Reviews
Virgilio's Cocktail Bar • $$
524 Duval St, Key West

“This is one of my favorite restaurants in Key West. The charcuterie was excellent, the Negroni was spot-on, and the seafood soup and pasta were delicious as always. The service was great, and the food came out in record time. I have only good things to say about this place. I will visit again the next time I'm in Key West.“

4.3 Superb231 Reviews
Fat Tuesday Key West Duval St Bar • $$
305 Duval St, Key West

Customers` Favorites

Strawberry Colada and Strawberry Mango
Duval

“Fat Tuesdays is a must when walking down Duval St. All the Bartenders are fun & friendly. Met 2 bartenders both named Savannah that were great. DJ music is live & exciting. Dog Friendly and they serve pup cups! So while we did Jello Shots our dog was able to have a pup cup.“

4.3 Superb83 Reviews
La Trattoria Restaurant Italian • $$
524 Duval St, Key West

Customers` Favorites

Spaghetti Alla Bolognese
Vitello Alla Parmigiana
Tortellini Alla Romana
Lasagna Alla Bolognese
Gnocchi Al Gorgonzola
Fettuccine Alfredo
Ravioli Trattoria
Chicken Marsala
Penne Venezia
Bread Service

“Ambiance is always great in downtown Key West. Our waiter was terribly slow. 15 minutes to take our drink order, 20 minutes to deliver drinks, over a half an hour to receive food, once ordered. Food was over-sauced. 3 of us ended up taking food home because the sauce was over whelming. I could not find the ravioli, shrimp or crab in the sauce. The 1 person who had the chicken piccata was happy. We have eaten at La Trat many times, and were happy. This time we were disappointed.“

4.2 Good351 Reviews
Shimp Daddys Bar • $$
908 Kennedy Dr, Key West

“I like this place. It's a cool little spot tucked away so you kind of have to know about it to find it. Our bartender, Bill, was attentive and on point. It's close to home, easy to bike or walk to if you live anywhere in new town. I give this place 2 thumbs up and 5 stars 😊“

4.4 Superb34 Reviews
General Horseplay Cocktail Bar • $$
423 Caroline St, Key West

Customers` Favorites

Curry Caramel Popcorn
Root of All Evil
Crime of Passion
Bella Vardier

“General Horseplay is a phenomenal bar. Bartender Eric waited on my wife and me. He was wonderful interpersonally, and he was a magician as a mixologist. I like to think of myself as educated when it comes to craft cocktails, yet he introduced me to the vieux carre, and it was delightful. I cannot recommend Eric and General Horseplay highly enough.“

4.3 Superb57 Reviews
Chart Room Cocktail Lounge Cocktail Bar • $$
1 Duval St, Key West

Customers` Favorites

John's Famous Simmering Red-Hot Pot
Popcorn

“We really struggled finding this from Google maps but with assistance we did and it was worth the effort. A very small bar with map charts all over the walls and ceiling. They usually have free hot dogs, peanuts and popcorn but apparently the hot dog crock pot wasn't working and although there was some popcorn the machine is on its last leg and we had more kernels than popped corn. None of this impacted the experience. It's an incredible spot that should be visited!!“

4.3 Superb34 Reviews
Liquor Store at Heroes Bar Cocktail Bar • $$
Inside Heroes Bar, 506 Southard St, Key West

“One of our favorite spots in Key West and always our first stop. Morne is a gem and one of the biggest reasons why we frequent this bar. He deserves many accolades. He is friendly, funny, warm and always mixes up a killer cocktail! We will continue to be regular patrons for years to come:)“

4.3 Superb12 Reviews
Four Marlins Oceanfront Dining Seafood • $$$
1435 Simonton St, Key West

Customers` Favorites

Fire Engine Steak and Eggs
Key Lime Pie N1 in the Keys
Tuna Avacado Toast
Shrimp and Grits
Citrous Grouper
Eggs Benedict
Scallops
Octopus
Fish

“After checking in to the Reach Curio Collection we decided to stay there for dinner. The Four Marlins was a superb experience. I recommend booking in advance so you can get a table outside overlooking the beach. It was a bit pricey however the food was perfectly executed and service by Fabiola was awesome. We shared the conch and crab fritters for appetizer and they were delicious. For dinner we had the NY strip which was extremely flavorful, the red snapper entree special that was delicious and the grouper entree that was amazing. We followed it all by the key lime pie and a fantastic croissant bread pudding with raisins, caramel and vanilla gelato. All was awesome and would def go back“

4.1 Good214 Reviews
Alonzo's Oyster Bar Seafood • $$
700 Front St, Key West

Customers` Favorites

Beer Steamed Shrimp 1 2 L B or 1 lb
Key Lime Pie a Must Try in the Keys
Raw Oysters on the Half Shell
Roasted Mussels Diablo
Coconut Fried Grouper
Florida Lobster Tail
Whole Fried Snapper
Sesame Seared Tuna
Peel & Eat Shrimp
Alaskan King Crab

“Christine H deserves more than 5 stars for her excellent friendly attentive service. She's very knowledgeable about the food, cocktails and the local area. A great personality.The terrace has a great location overlooking the harbour, and the food and drinks there are great.“

4.1 Good322 Reviews
First Flight Island Restaurant & Brewery American • $$
301 Whitehead St, Key West

Customers` Favorites

Spinach Salad with Diced Mango Sliced Red Onion and Roasted Walnuts in a Balsamic Vinaigrette
Brisket Mac and Cheese
Jerk Chicken Sandwich
Island Chicken Pasta
Beer Steamed Clams
Seafood Fettuccine
Scallop Appetizer
Whole Snapper
Deviled Eggs
Mac N Cheese

“Visited with our toddler and our server, Mica, was do accommodating. Good food, decent beer, cool patio. Only weird part was we seemingly entered from the back right onto the patio and it took us (and we watched several others wait and look) a bit to find the host for seating.They also had a wedding going on in their upper patio and it looked really nice!Kid-friendliness: Our server was very helpful and offered to find some off-menu choices that were more kid-friendly“

4.1 Good360 Reviews
Berlin's Cocktail Bar & Lounge Lounges • $$
700 Front St, Key West

Customers` Favorites

Classic Cocktails

“Last night, we had the opportunity to hear Bria Ansara sing! We've been going there for years and have missed her beautiful voice!! She always drew a crowd and last night was no different. I hope n pray Berlins comes to there senses and brings her back on a regular basis!! And the food n drinks were delicious as always...“

3.8 Good33 Reviews
Toasted Coconut Bar & Grill • $
3820 N Roosevelt Blvd, Key West

“Fresh ingredients and located by the pool at the 24 hotel. Food was great for the price. We had the French toast with strawberries and roasted banana syrup and the Cuban eggs Benedict. Local wildlife to watch while you swing from the wooden swing.“

3.6 Good30 Reviews
Pirate's Cove Key West Cocktail Bar • $$
619 Front St, Key West

Customers` Favorites

Bilge Breakfast Bagel
Main Deck Fish Tacos
Grilled Chicken
Conch Fritters
Full Breakfast
Curly Fries

“We came with a group of 12 the first night, then a group of 6 two nights later…waitress Crystal was super! The coconut shrimp, and curly fries were amazing. Another member of the party loved the mahi. Burgers were great as well. Definitely a hidden gem! Don’t miss it! Fresh and delicious!“

3.5 Good45 Reviews
Southernmost Beach Café Caribbean • $$
1405 Duval St, Key West

Customers` Favorites

Classic Key Lime Pie
Fresh Catch Sandwich
Avocado Toast Trio
Catch of the Day
Conch Fritters
Fried Calamari
Coconut Shrimp
Mahi Sandwich
Lobster Tail
Fish Tacos

“I recently stopped by the bar here for a drink and encountered a hiccup with their credit card system. However, bartender Sean stepped up and made the experience unforgettable.Despite the glitch, Sean remained cool and collected, handling the situation with ease. And he kept the atmosphere light with his friendly banter.What really stood out was Sean's genuine care for his customers. He went out of his way to ensure everyone was taken care of, checking in regularly and offering a helping hand where needed.Beyond his excellent customer service, Sean's drinks were spot on. He mixed up some fantastic cocktail and overall, despite the technical snag, Sean's stellar service turned what could have been a frustrating experience into a memorable one. Kudos to Sean for going above and beyond“

3.7 Good263 Reviews
The White Tarpon Bar & Restaurant Cocktail Bar • $$
700 Front St, Key West

Customers` Favorites

Jamaican Jerk Fried Shrimp
Conch Fritters
Key Lime Pie
Fish Tacos
Fish Dip
Salad

“A Culinary Gem Along Key West's Waterfront: The White Tarpon**A Gastronomic Delight:** If you're seeking an unforgettable culinary experience amidst the vibrant tapestry of Key West, look no further than The White Tarpon. Nestled along the scenic docks of A-B Marina, this hidden gem promises not just a meal, but a journey through the flavors of the Florida Keys.**Blackened Fish Tacos:** Prepare your taste buds for a symphony of flavors with their signature Blackened Fish Tacos, crafted from fresh yellowtail snapper. Each bite is a harmony of spices, perfectly complemented by the delicate texture of the fish.**Conch Fritters:** Dive into the essence of Key West cuisine with their succulent Conch Fritters, a true delicacy of the region. Crispy on the outside, tender on the inside, these fritters are a testament to the chef's mastery of traditional flavors.**Hummus Plate:** Elevating the dining experience with finesse, The White Tarpon offers a Hummus Plate that transcends ordinary appetizers. Fresh veggies, crisp sesame crackers, marinated olives, and creamy goat cheese come together in a symphony of textures and tastes, accented by the refreshing sweetness of watermelon.**A Slice of Key West Life:** Immerse yourself in the laid-back atmosphere of Key West as you dine amidst the gentle breeze and the sound of boats returning from their charters. The open-air ambiance of The White Tarpon sets the stage for relaxation and indulgence.**Impeccable Service:** From the moment you step foot in this culinary haven, you're greeted with warm hospitality and attentive service. The staff at The White Tarpon are dedicated to ensuring that every aspect of your dining experience exceeds expectations.**Key Lime Pie:** No visit to Key West is complete without savoring a slice of authentic Key Lime Pie, and The White Tarpon delivers perfection in every bite. Pair it with a cup of coffee for a blissful conclusion to your meal.**Worth Every Penny:** While the prices may be slightly higher than neighboring establishments, the unparalleled quality of the cuisine and the serene atmosphere make every dollar spent at The White Tarpon worth it. At around $40 per person plus tip, it's an investment in an experience you'll cherish forever.**Final Verdict:** In a town brimming with culinary delights, The White Tarpon stands out as a shining star. With its exceptional food, inviting ambiance, and impeccable service, this establishment is not just a restaurant – it's an experience. Whether you're a visitor or a local, do yourself a favor and treat your palate to the wonders of The White Tarpon. It's no wonder why it could easily merit consideration for a Michelin star.**Bon Appétit and Happy Dining!**Thomas CorraoStray Compass Restaurant Reviews#straycompasslife“

3.6 Good72 Reviews
SIMONEY'S Cocktail Bar • $$
1405 Duval St, Key West

“I cannot find a more beautiful on the beach location to enjoy a wonderfully prepared dinner. The service was friendly, attentive and professional. The Mahi Mahi was flaky and juicy. It felt like a dinner on a Caribbean island. It was pricey but worth visiting. Enjoy!!“

3.5 Good136 Reviews
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