22 Best Cocktail Bars in Key West

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

Customers` Favorites

Charcuterie & Cheese Board
Guinness Potato Chips
Charcuterie Plate
Lemon Drop
Caviar

“Bartender alone ! She made an Outstanding Old Fashion and grapefruit Martini.“

4.6 Superb140 Reviews
Chart Room Cocktail Lounge Cocktail Bar • $
1 Duval St, Key West

Customers` Favorites

John's Famous Simmering Red-Hot Pot
Popcorn

“Small place with a great vide. Jimmy's first gig was allegedly here. We didn't eat anything. Seems like that could be true. A little hard to find but just wind your way around the resort and you'll stumble across it. It doesn't open until the evening. A++ old school OG KW hangout.“

4.5 Superb59 Reviews
General Horseplay Cocktail Bar • $$
423 Caroline St, Key West

Customers` Favorites

Curry Caramel Popcorn
Happy Dagger Be Brief
Root of All Evil
Crime of Passion
Moscow Mule GH
Bella Vardier
Murricane

“Had a blast! You exceeded all of my expectations with your tequila selection last night. From your single barrel Fortaleza “Horse Play” to the G4 6 barrel and the other extensive selection. Killer atmosphere def sets you apart from everywhere else. The DJ out back was sick and we will be back.Keep up the good work!“

4.4 Superb154 Reviews
The White Tarpon Bar & Restaurant Cocktail Bar • $$
700 Front St, Key West

Customers` Favorites

Jamaican Jerk Fried Shrimp
Smoked Fish Dip
Conch Fritters
Steamed Mussels
Key Lime Pie
Hummus Plate
Caesar Salad
Raw Oysters
Fish Tacos
Sandwich

“Wonderful time. Great happy hour!“

4.2 Good174 Reviews
Milagro Restaurant and Bar Bar • $$$
1401 Simonton St, Key West

Customers` Favorites

Petite Filet Mignon Medallions & Pink Shrimp
Pan Seared Shrimp & Scallops Veracruz
Stacked Blue Corn Enchiladas
Rosemary Roasted Prime Rib
Seared Yellowtail Snapper
El Corazon Margarita
Classic French Onion
Wood Grilled Octopus
Mashed Potatoes
Shrimp Cocktail

“⭐️⭐️⭐️⭐️⭐️ Absolutely Amazing Experience! From start to finish, everything was exceptional! The food was fresh, flavorful, and beautifully presented — truly some of the best we’ve had in a long time. The drinks were perfectly crafted and delicious, and the service was outstanding — friendly, attentive, and made us feel so welcome. Every detail was spot-on, and we can’t wait to come back. Highly recommend to anyone looking for great food, great service, and a great atmosphere!“

4.6 Superb473 Reviews
Pirate's Cove Key West Cocktail Bar • $
619 Front St, Key West

Customers` Favorites

Bilge Breakfast Bagel
Main Deck Fish Tacos
Corned Beef Hash
Grilled Chicken
Conch Fritters
Full Breakfast
Curly Fries
Hamburger

“great food, good prices. beautiful view“

3.9 Good81 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

“Perfect location on Duval! Easy walk to beach, bars, and restaurants. Extremely friendly and helpful staff. Rooms have everything you need, refrigerator, microwave, toaster, beach chairs, beach towels, information on local attractions, I could go on and on… Oh and the fact that the rum bar is right downstairs is very convenient, maybe too convenient, lol! 🍹🥴“

4.7 Superb177 Reviews
Heroes Bar and Liberty Lounge Sports Bar • $
506 Southard St, Key West

“I love this bar! Very laid back, staff is awesome, and a great place to just hang out.“

4.8 Superb122 Reviews
Lolita's Coastal Cocina Mexican • $$
245 Front St, Key West

“Lolita’s nails fresh, flavorful coastal dishes with a relaxed, bright atmosphere. From perfectly seasoned seafood to crisp, refreshing sides, every bite feels thoughtful.

The staff are friendly and helpful, and the setting makes it ideal for a casual lunch and dinner.“

4.7 Superb65 Reviews
Fat Tuesday Key West Duval St Bar • $
305 Duval St, Key West

Customers` Favorites

Strawberry Colada and Strawberry Mango
The Travel Mug Filled with Daiquiri
Call a Cab and Pina Colada Mixed
Chocolate Covered Strawberries
Chocolate-Covered Strawberry
Rum Runner and Miami Vice
Banana Banshee
Call Liquors
Bush Wacker
Dreamcicle

“Here’s a Yelp-style review for Fat Tuesday in Key West:

Fun, lively spot with great energy and friendly staff right in the heart of Key West! Their frozen drinks are delicious and perfect for sipping while you stroll Duval Street. The premade shots are definitely pricey, but the convenience and fun vibe make it worth it plus they’re strong and flavorful. A great place to kick off your night, grab a drink, and soak in the party atmosphere! 🍹🎉“

4.4 Superb151 Reviews
Bel Mare Restaurant Fine Dining • $$$
700 Front St, Key West

Customers` Favorites

Caprese with Burrata Salad
Oysters on the Half Shell
Scallops & Pork Belly
Chocolate Temptation
Wild Mushroom Risotto
Shrimp Orecchiette
Key Lime Desert
Pistachio Gelato
Lobster Scampi
Veal Bolognese

“My husband and I have been coming here for years. It’s exceptional. We never have any problems with dietary restrictions and the service is 10/10“

4.3 Superb420 Reviews
Virgilio's Cocktail Bar • $$
524 Duval St, Key West

“Great cuisine and great drinks . Always the best live entertainment on the Island !“

4.3 Superb366 Reviews
Liquor Store at Heroes Bar Cocktail Bar • $
Inside Heroes Bar, 506 Southard St, Key West

“I love this bar! Very laid back, staff is awesome, and a great place to just hang out.“

4.2 Good10 Reviews
Berlin's Cocktail Bar & Lounge Lounges • $$
700 Front St, Key West

Customers` Favorites

Maine Lobster & Escargot
Classic Cocktails

“Best place in Key West for dinner and cocktails“

4.2 Good56 Reviews
Follow The Rabbit Bar Bar • $
404 Southard St, Key West

“This place is incredible!“

4.2 Good164 Reviews
La Trattoria Restaurant Italian • $$$
524 Duval St, Key West

Customers` Favorites

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

“The food was excellent; my wife had the hog fish special and I had the chicken parmigiana. We split chocolate mousse for dessert. The service was excellent. Highly recommended!!“

4.2 Good578 Reviews
Four Marlins Oceanfront Dining Seafood • $$$
1435 Simonton St, Key West

Customers` Favorites

Key Lime Pie N1 in the Keys
Fire Engine Steak and Eggs
Conch and Crab Fritters
Lobster Mac and Cheese
Four Marlins Salad
Tuna Avacado Toast
Hummingbird Cake
Shrimp and Grits
Citrous Grouper
Fish and Chips

“Stayed at the Reach and ate here a few times. Had the Cobb salad - which I could have eaten every day 👩🏻‍🍳 😘. Also had the Nutella French toast. Another item I could eat daily !!! The decor is stunning , the service is fabulous & how can you beat oceanfront location !!“

4.1 Good382 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
Lobster Mac and Cheese
Coconut Fried Grouper
Florida Lobster Tail
Whole Fried Snapper
Baked Oyster Combo
Sesame Seared Tuna

“Oh my gosh! Best place ever! Amazing oysters and amazing buffalo shrimp. But most of all the service! Wells was our waitress and she was AMAZING!!! Thank you for making our experience wonderful!!!“

4.1 Good534 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
Seafood Fettuccine
Beer Steamed Clams
Bavarian Pretzel
Scallop Appetizer
Brewery Wings
Brisket Panini

“What impressed me the most was that I noted in our reservation that we were celebrating a friend's birthday. The hostess and waiter noted that we were celebrating a birthday. At the end of dinner, none of us ordered dessert, but the waiter brought out a complimentary piece of key lime pie with a large sparkler in it and the words Happy Birthday written in chocolate on the plate - a class act. At most restaurants, one has to ask for this type of amenity. In this case, it was unexpected and welcome.“

4.1 Good601 Reviews
Toasted Coconut Bar & Grill • $
3820 N Roosevelt Blvd, Key West

Customers` Favorites

Cheeseburger

“The cutest Tiki Bar Restaurant of all the hotels in KW! Best drinks and snacks when hanging around the pool! Jennifer and Milly are absolute Queens ?? with making drinks! They can help you with anything you need! I even tried taking them home with me ??‍♀️ I can't wait to come back! ?“

3.5 Good48 Reviews
Southernmost Beach Café Caribbean • $$
1405 Duval St, Key West

Customers` Favorites

Classic Key Lime Pie
Fresh Catch Sandwich
Southernmost Salad
Avocado Toast Trio
Catch of the Day
Breakfast Tacos
Fried Calamari
Conch Fritters
Coconut Shrimp
Cuban Benedict

“The view for our breakfast was just right. Loved it. We had the bagel with all the fixings, I thought it was priced reasonable for the area and defiantly how large the portions were. My wife had the eggs Benedict with large lobster pieces on the top. She enjoyed it very much. The Bloddy Marys were in my opinion just okay.“

3.8 Good461 Reviews
The Stoned Crab Seafood • $$
3101 N Roosevelt Blvd, Key West

Customers` Favorites

Flash-Fried Baby Calamari Basket
Our Fishermen's Combo Basket
The Big Chill Seafood Tower
Old Bay Stone Crab Steamer
Oysters on the Half Shell
Key West Lobster Steamer
Florida Lobster Tail
Peel and Eat Shrimp
Frituras de Pescado
Snow Crab Clambake

“Best fresh seafood restaurant in Key West, or anywhere in the keys. Consistently fresh consistently good. Pleasant staff“

3.5 Good425 Reviews

Cocktail Bars Nearby