25 Best Cocktail Bars in Key West

The Roost Cocktail Bar • $$
508 Fleming Street, 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.“

4.7 Superb287 Reviews
Chart Room Cocktail Lounge Cocktail Bar • $
1 Duval Street, Key West

Customers` Favorites

John's Famous Simmering Red-Hot Pot
Popcorn

“Atmosphere alone rate 5+ stars. Free hotdogs, peanuts and popcorn. 💯 Mark the bartender was friendly and told me about some of the history. I love Key West history and this is true Key West history. I might just become a regular here.“

4.6 Superb141 Reviews
General Horseplay Cocktail Bar • $$
423 Caroline Street, 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!“

4.5 Superb308 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 Superb612 Reviews
The White Tarpon Bar & Restaurant Cocktail Bar • $$
700 Front Street Suite 105, 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!“

4.4 Superb344 Reviews
The Rum Bar Bar • $$
1117 Duval Street, 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 Superb405 Reviews
Heroes Bar and Liberty Lounge Sports Bar • $
506 Southard Street, Key West

“This place is wonderful, they represent those who with respect & honor. To all who serve thank you for your service & sacrifice 🫡🇺🇸 🏆🥇“

4.8 Superb192 Reviews
Pirate's Cove Key West Cocktail Bar • $$
619 Front Street, Key West

Customers` Favorites

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

“best bang for the buck in key west, the new bartender, Robin knows how to mix a drink.“

3.9 Good136 Reviews
Fat Tuesday Bar • $
305 Duval Street, 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

“Stopped by Fat Tuesday in Key West and had a fantastic experience! Savannah was an amazing bartender—friendly, welcoming, and made great recommendations. She suggested the Key Lime Colada, and it was absolutely delicious... definitely one of the best frozen drinks I've had in Key West. If you stop by, ask for Savannah and give the Key Lime Colada a try. You won't be disappointed!“

4.5 Superb409 Reviews
Flama Cabana Bar • $$
3420 North Roosevelt Boulevard, Key West

“Not a cigar bar, but it’s also pretty obvious it’s just a bar that sells cigars. Great outdoor veranda for smoking cigars is available.
The bartender is awesome and always engaging with guests.
Small bites a very good and appropriate for the Cuban themed atmosphere.“

4.5 Superb23 Reviews
Four Marlins Oceanfront Dining Seafood • $$$
1435 Simonton Street, 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 Good571 Reviews
Elevate Skye Bar & Lounge Bar •
245 Front Street, Key West
5 Superb2 Reviews
Virgilio's Cocktail Bar • $$
524 Duval Street, Key West

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

4.3 Superb526 Reviews
Bel Mare Restaurant Fine Dining • $$$
700 Front Street, Key West

Customers` Favorites

Caprese with Burrata Salad
Oysters on the Half Shell
Wild Mushroom Risotto
Chocolate Temptation
Scallops & Pork Belly
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 Superb561 Reviews
Liquor Store at Heroes Bar Cocktail Bar • $
Inside Heroes Bar, 506 Southard Street, Key West

“This place is wonderful, they represent those who with respect & honor. To all who serve thank you for your service & sacrifice 🫡🇺🇸 🏆🥇“

4.3 Superb12 Reviews
Tin Cup Chalice Bar & Grill American •
2018 South Roosevelt Boulevard, Key West

“Usually the hotel bar is just ok HOWEVER this spot was AWESOME! Staff were very friendly! Drinks were cold and delicious. Never a wait and always quick service. Now I cannot begin to tell you how AMAZING the coconut shrimp was. OMG. Best shrimp I’ve ever had hands down. The Thai sauce that it’s served with is phenomenal. We had it everyday during our stay. Amazing hotel - separate glowing review!“

3.9 Good9 Reviews
Berlin's Cocktail Bar & Lounge Lounges • $$
700 Front Street, Key West

Customers` Favorites

Maine Lobster & Escargot
Classic Cocktails

“Best place in Key West for dinner and cocktails“

4.2 Good98 Reviews
Follow The Rabbit Bar Bar • $
418 Eaton Street, Key West

“This place is incredible!“

4.2 Good210 Reviews
Lolita's Coastal Cocina Mexican • $$
245 Front St, Key West

Customers` Favorites

Grilled Street Corn and Sides
Tacos and Mexican Corn
Gulf Shrimp Ceviche
Taco Bar Guacamole

“This place just may be the best Mexican restaurant in all of Key West! Our lovely bartender Heather treated us like family and made our experience even more blissful. If you are looking for exceptional dining, outstandingly friendly service, and incredible atmosphere this IS the place.“

4.2 Good292 Reviews
First Flight Island Restaurant & Brewery American • $$
301 Whitehead Street, 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

“Don’t walk, RUN AND EAT HERE! My son came from Philly to visit me and we came to Key West via the Key West Express. This place IS EVERYTHING! The hostess and the guy at bar both super welcoming and kind. A rooster walking through the restaurant caught us off guard, lol! But it made the place even more cool! My son had the jerk chicken sandwich. I don’t remember seeing him chew it… that’s how good it was! HE LOVED IT! I had the caprese… OMG! It made no sense how delish the food was! And it was unbelievably reasonable. I will sho nuff be back! 🔥⭐😊“

4.2 Good870 Reviews
La Trattoria Restaurant Italian • $$$
524 Duval Street, 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 Good874 Reviews
Alonzo's Oyster Bar Seafood • $$
700 Front Street, 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!!!“

4.2 Good973 Reviews
Toasted Coconut Bar & Grill • $
3820 North Roosevelt Boulevard, Key West

Customers` Favorites

Cheeseburger

“Enjoyed our stay at the Blue Flamingo and really enjoyed the chicken and waffles and omelette meals!! Very nice service. Chickens and hotel vibes. Only sad part is the breakfast menu is a little limited and it's more of a lunch and dinner menu and the atmosphere is super pool side but I don't think you could eat pool side unless at a table.“

3.8 Good90 Reviews
Southernmost Beach Café Caribbean • $$
1405 Duval Street, 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

“2025 Key West Caravan with Central Florida Corvette Association (CFCA) friends - we come every year. This year we discovered the Southernmost Beach Cafe- Very Nice... Great breakfast feast, great service and a wonderful atmosphere looking right out at the beach. Update October 2026 13 of the CFCA member made a return trip to the Southernmost Beach Cafe and once again we are so glad that we did . Food was great and the service was wonderful. Obie & Ramona Young ** OBIE ** Florida Aviation Network“

3.9 Good833 Reviews
The Stoned Crab Seafood • $$
3101 North Roosevelt Boulevard, 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
Old School Conch Fritters
Key West Lobster Steamer
Florida Lobster Tail
Frituras de Pescado
Peel and Eat Shrimp

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

3.4 Good840 Reviews

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