25 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 Superb270 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 Superb596 Reviews
Chart Room Cocktail Lounge Cocktail Bar • $
1 Duval St, Key West

Customers` Favorites

John's Famous Simmering Red-Hot Pot
Popcorn

“Small intimate history packed bar tucked away in the Pier House resort. Jerry Jeff Walker took Jimmy Buffett here in 1971. It was Jimmy’s first paid gig. Friendly welcoming bartender enjoys customers in search of Jimmy Buffett history. He provides kool info about former famous patrons. Pricey drinks but well worth a visit. Free shell peanuts, popcorn and hot dogs 🌭!!“

4.5 Superb130 Reviews
The White Tarpon Bar & Restaurant Cocktail Bar • $$
700 Front St #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 Superb315 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 Superb298 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 Superb387 Reviews
Heroes Bar and Liberty Lounge Sports Bar • $
506 Southard St, 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 Superb183 Reviews
Fat Tuesday 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

“My husband and I walked past Fat Tuesday a few different times while we were in Key West, and honestly I wish we would’ve stopped in sooner! The music from the DJ outside was always great and really helped set the fun vacation vibe, even though it surprisingly wasn’t super busy when we went.

I absolutely love frozen drinks, so one night we decided to finally go in, and it ended up being one of our favorite stops of the trip. I got the Bushwacker frozen drink, which sounded kind of strange at first, but it literally tasted like a chocolate Frosty from Wendy’s — absolutely amazing. 10/10 highly recommend trying it!

The bartender was a super cute young blonde girl who was incredibly knowledgeable and honest about the drinks, which I really appreciated. I asked about a banana-flavored drink and she straight up told me they don’t even carry it anymore because it was so bad 😂 That honesty honestly made me trust her recommendations even more, and she definitely pointed us in the right direction.

They also had really cute Key West themed T-shirts about drinking, vacationing, and not wanting to go back home, and I ended up buying two in the prettiest pastel colors.

Overall, such a fun stop with amazing drinks, good music, and great service. We’ll definitely be back the next time we’re in Key West!“

4.5 Superb373 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“

3.8 Good135 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 is the perfect place to dine if you port stop in Key West during a cruise! The restaurant is beautiful and inviting, with authentic decor. I had the Brioche French Toast, and it was delicious! I loved everything about it. I paired my meal with a mimosa, which was the perfect choice with my meal. If I'm ever in Key West again, I will dine at Lolita's ❤.“

4.4 Superb145 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 Good541 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 Superb517 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 Superb539 Reviews
Flama Cabana Bar • $$
3420 N Roosevelt Blvd, Key West

“Stopped by Flama Cabana at Havana Cabana this past weekend and had such a great experience. The atmosphere is exactly what you want in the Keys…fun, relaxed, and full of personality.

Tosha was our bartender and she was absolutely amazing. Super friendly, high energy, and on point the entire time. Drinks came out quickly, were made perfectly, and she made us feel welcome from the moment we sat down. You can tell she genuinely enjoys what she does, and it shows.

I brought a friend who had never been before, and she’s already asking to go back—that says everything.

Between the vibe, the drinks, and the service, this place is definitely a gem. Highly recommend stopping in, especially if Tosha is behind the bar.“

4.6 Superb19 Reviews
Elevate Skye Bar & Lounge Bar •
245 Front St, Key West
5 Superb2 Reviews
Liquor Store at Heroes Bar Cocktail Bar • $
Inside Heroes Bar, 506 Southard St, 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 S Roosevelt Blvd, Key West
3.7 Good3 Reviews
Follow The Rabbit Bar Bar • $
404 Southard St, Key West

“This place is incredible!“

4.2 Good185 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 Good835 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!!!“

4.2 Good901 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 Good96 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! ?“

3.4 Good88 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 are very fortunate to be staying at the resort and figure that there isn't anything better than this.... We are oceanfront with delicious food and drinks. And we don't have to travel too far! The staff have been extremely accommodating and absolutely lovely. The food was outstanding.“

3.8 Good797 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

“I was so impressed by the service. Top notch. The manager noticed that my teen son was starving and brought him an additional deviled egg when all had been eaten. They also have a dog menu. My pup had water an a sweet treat. Brewmaster fries and brisket Mac and cheese were divine. Thank you for an awesome 4th experience!“

4 Good837 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 Good779 Reviews

Cocktail Bars Nearby