21 Best Cocktail Bars in Key West

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

Customers` Favorites

John's Famous Simmering Red-Hot Pot
Popcorn

“This is a must stop of you are a Jimmy Buffett fan! Very small place and seating is very limited. They offer free popcorn, peanuts and hot dogs for food. Great drinks and domestic beers with at least one craft choice on bottles.
The place is a shrine to the characters of old Key West and of course where Jimmy got his start in 1971. Talk to the bartenders and they'll tell you great stories of the old days.“

4.2 Good35 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

“Celebrated my 30th birthday here and it was by far the best food we ate in Key West. We ordered the Asiago bread and squid for our appetizers. The squid was FABULOUS!!! I’ve been craving it since! For dinner we did the wahoo, swordfish, prime rib and chicken. All of which we were each raving about to each other! The atmosphere was dimmed candle lit tables and our server was great! Highly recommend for anyone wanting to taste high end food and it be up to par! Will definitely be back!“

4.6 Superb511 Reviews
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.“

4.8 Superb92 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

“⭐️⭐️⭐️⭐️⭐️
We absolutely love coming here every time we’re in Key West — it’s one of our must-stop spots! This visit started a little rough when the Caesar salad came out with stale croutons, but the staff couldn’t have handled it better. They immediately made a fresh one, and it ended up being the best Caesar salad we’ve ever had — perfectly crisp, creamy, and balanced. The executive chef himself brought it out to check on us and make sure everything was right, which says a lot about how much they care.

Every visit reminds us why this place is one of our favorites — the food, the service, and the kindness behind it all. Highly recommend!“

3.7 Good441 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 Superb126 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!“

4.1 Good85 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“

3.6 Good41 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 Superb107 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 Superb68 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

“If you’ve ever wondered what it’s like to mainline gasoline in slushy form, welcome to Fat Tuesday Key West. The 190 Octane (153 proof grain alcohol + orange punch) is basically jet fuel with a citrus twist — I’m 90% sure my rental scooter ran better after I spilled some on it.

The flavors here range from “fun beach vacation” (Piña Colada) to “pray for my liver” (Cat 5 Hurricane) to “this is how Florida Man is born” (Mardi Gras Mash with bourbon + triple sec). You can even get a 128oz gallon to go — because nothing says “responsible tourist” like walking down Duval Street with a jug of neon alcohol that could double as antifreeze.

I got the Souvenir Squeeze Bottle thinking it was cute. Turns out, it’s basically a lifetime commitment — you’ll be refilling it until your doctor writes you a letter.

Also, big respect to the Skinny Watermelon Daiquiri: same 153-proof grain alcohol, just “half the calories.” Because obviously the calories were the dangerous part.

By the time I mixed 190 Octane Blue Raspberry with Mango Tango and topped it with Spicy Margarita, I’m pretty sure I accidentally discovered the cure for jet lag — or possibly astral projected into Jimmy Buffett’s backyard.

Pro tip: Hydrate, wear sunglasses, and maybe text your mom before your third refill, because after that it’s anybody’s guess what your night (or your Instagram stories) will look like.

Would I come back? Yes. Should you? Only if your insurance is paid up.

🍹🌴 #FrozenDecisions #DuvalStreetScience“

4.4 Superb96 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 Superb460 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 Superb396 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“

4.6 Superb20 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.“

5 Superb6 Reviews
Follow The Rabbit Bar Bar • $
404 Southard St, Key West

“This place is incredible!“

4.2 Good169 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
Fettuccine Alfredo
Ravioli Trattoria
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 Good573 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 Good22 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

“Romantic dining with the most creative entrees . Such a memorable experience“

4.1 Good385 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 Good499 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
Scallop Appetizer
Brisket Panini
Whole Snapper
Deviled Eggs

“The prices and portions were great. The food probably would have been good but the server neglected to bring it when it was ready. Food was cold and weakly seasoned. Server also added in a huge gratuity for herself even though we were just a party of five. The manager did a great job adjusting the bill and was very apologetic for the issues.“

4.1 Good586 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“

3.4 Good378 Reviews

Cocktail Bars Nearby