17 cocktail bar places in Key West we have eaten in, sorted by editor score. All cuisines in Key West | Cocktail Bar across every city.
The Green Parrot ★ 4.8
old-town · 601 Whitehead Street, Key West, FL 33040
The Green Parrot has poured at Whitehead and Southard since 1890 by its own count, Key West's open-shuttered dive with free popcorn and nightly bands.
Sloppy Joe's Bar ★ 4.4
duval-street · 201 Duval Street, Key West, FL 33040
Sloppy Joe's opened with Prohibition's end in 1933 and has held Duval and Greene since 1937, a National Register Key West saloon with all-day live music.
Captain Tony's Saloon ★ 4.3
duval-street · 428 Greene St, Key West, FL 33040
Captain Tony's Saloon drinks inside an 1851 icehouse on Greene Street, the Key West bar that claims Hemingway's patronage and a tree through the roof.
Schooner Wharf Bar ★ 4.4
historic-seaport · 202 William Street, Key West, FL 33040
Schooner Wharf Bar has held the old Singleton shrimp-factory site on Key West's bight since 1984, an open-air deck of roosters, rum and live music.
Hog's Breath Saloon ★ 4.0
duval-street · 400 Front Street, Key West, FL 33040
Hog's Breath Saloon works an open-air corner near Mallory Square, the Key West room of a saloon brand founded in Florida in 1976, with all-day bands.
The Rum Bar ★ 4.6
duval-street · 1117 Duval St, Key West, FL 33040
The Rum Bar pours one of Key West's deepest rum lists on the Speakeasy Inn porch, an upper Duval house whose basement once hid Prohibition bottles.
General Horseplay ★ 4.3
historic-seaport · 423 Caroline Street, Key West, FL 33040
General Horseplay mixes proper cocktails and pours craft beer on Caroline Street in Key West, with a hidden back bar opening nightly at 19:00.
Mary Ellen's Bar & Kitchen ★ 4.2
old-town · 420 Appelrouth Lane, Key West, FL 33040
Mary Ellen's serves grilled cheese down an Appelrouth Lane alley until 02:00, the late Key West kitchen that beats a pizza slice after Duval Street.
Tiki House ★ 4.1
duval-street · 203 Duval Street, Key West, FL 33040
Tiki House shakes zombies and mai tais with fresh fruit on lower Duval in Key West, the island's dedicated tiki room from the Horseplay bar family.
The Smallest Bar ★ 4.0
duval-street · 124 Duval St, Key West, FL 33040
The Smallest Bar squeezes a full Key West cocktail list into 72 square feet on lower Duval, claiming the title of the tiniest bar in the United States.
Berlin's Cocktail Bar & Lounge ★ 4.4
historic-seaport · 700 Front Street, Key West, FL 33040
Berlin's hides behind A&B Lobster House above Key West's harbour, a leather-chair speakeasy the operator dates as a local favourite since 1947.
Chart Room Bar ★ 4.2
duval-street · 1 Duval Street, Key West, FL 33040
The Chart Room hides inside the Pier House Resort at mile zero of Duval, the wood-panelled Key West bar once frequented by Jimmy Buffett and Mel Fisher.
The Roost ★ 4.3
old-town · 508 Fleming St, Key West, FL 33040
The Roost pairs serious old fashioneds with caviar service half a block off Duval in Key West, doubling as the neighbourhood's corner liquor store.
Irish Kevin's ★ 4.0
duval-street · 211 Duval Street, Key West, FL 33040
Irish Kevin's has run singalong sets on lower Duval since July 1998, a Key West show bar pouring Irish beer with a kitchen that serves until 23:00.
Willie T's ★ 4.0
duval-street · 525 Duval Street, Key West, FL 33040
Willie T's papers its Duval Street porch in signed dollar bills and pours mojitos over live music from 11:00 to 01:30, with a full Key West seafood menu.
The Roost ★ 4.3
old-town · 508 Fleming St, Key West, FL 33040
The Roost pairs serious old fashioneds with caviar service half a block off Duval in Key West, doubling as the neighbourhood's corner liquor store.
Chart Room Bar ★ 4.2
duval-street · 1 Duval Street, Key West, FL 33040
The Chart Room hides inside the Pier House Resort at mile zero of Duval, the wood-panelled Key West bar once frequented by Jimmy Buffett and Mel Fisher.