The best bars & nightlife in Key West

11 bars & nightlife we’ve checked and stand behind — with the story on each one. Not a ranking; a record.

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Nightlife · 11 places · showing the latest additions first

Craving something other than boat drinks? Vinos on Duval pours a deep by the glass lineup plus bubbles, spritzes, and dessert sips, and…

810 Duval St

Craving something other than boat drinks? Vinos on Duval pours a deep by the glass lineup plus bubbles, spritzes, and dessert sips, and lets you build your own cheese and charcuterie board with hummus and snacky spreads. Easy, cozy, very Key West...

From the Key West newsletter, September 17, 2026

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If your home bar is feeling a little too well behaved, General Horseplay leans into its "cocktails & tomfoolery" mantra with inventive…

423 Caroline St

If your home bar is feeling a little too well behaved, General Horseplay leans into its "cocktails & tomfoolery" mantra with inventive drinks, tasty beers, world wines, and actually good bar bites, plus a lively back bar that turns casual hangouts into proper Key West nights.

From the Key West newsletter, September 11, 2026

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Born in the 1960s and still wonderfully unpretentious, Chart Room Cocktail Lounge hides inside Pier House Resort & Spa with nautical charm,…

1 Duval St

Born in the 1960s and still wonderfully unpretentious, Chart Room Cocktail Lounge hides inside Pier House Resort & Spa with nautical charm, rum punch, and regulars who actually remember the stories. Think hot dogs, popcorn, and peanuts with your cocktails, plus that easy island vibe locals never take for granted.

From the Key West newsletter, September 3, 2026

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Shots & Giggles nails that cozy, no-drama bar vibe locals love, with a solid mix of beers, wines, and spirits. Open since 2011, it’s where…

201 Ann St

Shots & Giggles nails that cozy, no-drama bar vibe locals love, with a solid mix of beers, wines, and spirits. Open since 2011, it’s where easy conversation meets occasional game-day cheers, and they’ll happily host your next small celebration if you ask nicely.

From the Key West newsletter, September 15, 2026

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Since 1890, Green Parrot Bar has been the island’s go-to for unpretentious live music, a beloved jukebox, and community nights like Ukulele…

601 Whitehead St

Since 1890, Green Parrot Bar has been the island’s go-to for unpretentious live music, a beloved jukebox, and community nights like Ukulele Night and Charity Bingo. When you want live tunes without the frills, this is where the groove finds you.

From the Key West newsletter, September 8, 2026

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Tiki House

Nightlife

Tiki House shakes up authentic-and-inventive rum cocktails with retro South Seas vibes, live music, and the occasional Iron Bartender…

203 Duval St

Tiki House shakes up authentic-and-inventive rum cocktails with retro South Seas vibes, live music, and the occasional Iron Bartender showdown that’s weirdly inspiring. Take a Tiki Cocktail Class or grab the Mermaid Mug, then let the whole see-hear-feel-drink experience do its transporting thing this week.

From the Key West newsletter, August 30, 2026

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The Bull

Nightlife

Whether you want a cold draft, a classic pour, or just some Old Town breeze, The Bull is the rare open-air spot where local musicians play…

224 Duval St

Whether you want a cold draft, a classic pour, or just some Old Town breeze, The Bull is the rare open-air spot where local musicians play nightly and the people-watching is elite. Slide in, claim a table, let the street scene roll by and call it 'research'.

From the Key West newsletter, August 25, 2026

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Whether you want to even out that farmer's tan or just take in the bird's-eye view, Garden of Eden is the clothing-optional rooftop where…

224 Duval St

Whether you want to even out that farmer's tan or just take in the bird's-eye view, Garden of Eden is the clothing-optional rooftop where locals sip cold ones, stash cameras and cell phones, and dance under the stars with nightly DJ tunes. Relaxed, cheeky, pure Key West if you need a rooftop reset this week.

From the Key West newsletter, September 22, 2026

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Tipsy Rooster Liquor Store & Bar does the Key West two-step, pouring house-infused specialty cocktails while lining the shelves with…

1325 Simonton St

Tipsy Rooster Liquor Store & Bar does the Key West two-step, pouring house-infused specialty cocktails while lining the shelves with bottles distilled right here in town. Drop in this week for daily live music and grab something great for later, because your porch happy hour deserves an upgrade.

From the Key West newsletter, August 23, 2026

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Burgers & tacos with a twist spotlighted at a convivial hangout featuring a courtyard & live music.

409 Caroline St (Naval Air Station Key West)

Burgers & tacos with a twist spotlighted at a convivial hangout featuring a courtyard & live music.

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When you want a proper pint and zero fuss, Brady's Pub Key West nails it with perfectly poured Guinness, hearty Irish mains, and…

1900 Flagler Ave

When you want a proper pint and zero fuss, Brady's Pub Key West nails it with perfectly poured Guinness, hearty Irish mains, and comfort-food staples. It’s a go-to for locals to catch the game on wall-to-wall TVs, toss real darts, and peek at the Barking Parrot Gallery featuring local artists, plus weekly specials.

From the Key West newsletter, September 1, 2026

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