Cocktail Bar guide · 3 picks · Updated August 2026

Best Cocktail Bar Happy Hours in Key West, FL

Key West, FL has 3 cocktail bar spots with happy hour specials on the Key West happy hours page, part of 111 Key West menus with prices. Our #1 cocktail bar pick is The Roost (happy hour Daily 12-6), and deals start around $8 at Bar 1. The 3 below count down from #3 to #1, each with its happy hour window, the deal, and a link to the full menu.

Cocktail Bar spots

107

Happy hours

111

Menus with prices

Food deals

The 3 Best Cocktail Bar Happy Hours in Key West, counting down to #1

Ranked by a confirmed happy hour window, menu depth, and Google rating. Every pick links to the venue's full menu on DiscoverHappyHours.

3. General Horseplay

4.7 (626)Cocktail Bar Restaurant

423 Caroline St

174 items, 151 with prices

La Marca Prosecco$12I Pity A Fool$16Wake Up, Buttercup$20

See General Horseplay menu →See the menu →

2. Bar 1

4.7 (23)Cocktail Bar Restaurant

291 Front St Ste 207

Happy hour

Daily · 4pm-6pm

Drinks

Well Drinks $8; Select Wines $8; Classic Daiquiri $8; Chatham Artillery Punch $8; Mary Pickford $8

Food

Locally Smoked Fish Dip $8; "Cohiba Cigar" Rolls $8; Pickled Delight $8; Tia's Flan $8

12 items, 12 with prices

Locally Smoked Fish Dip$8"Cohiba Cigar" Rolls$8Pickled Delight$8

See Bar 1 menu →See the menu →

#1 pick

1. The Roost

4.7 (358)Cocktail Bar Restaurant

508 Fleming St

Happy hour

Daily · 12-6

Drinks

$10 Tap Drink of the Day; $10 Stoli Elit Martinis; select wine and beer specials

Food

$6 Deviled Rooster Eggs; ½ priced Caviar

48 items, 28 with prices

Olive You$12Keys Nuts$9Parmigiano Roosticano$12

See The Roost menu →See the menu →

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Happy Hours by Cuisine in Key West

Restaurant(39)Bar(20)American(14)Seafood(10)Caribbean(7)Italian(7)Pub(3)

Frequently Asked Questions

Where are the best cocktail bar happy hours in Key West?

We found 3 cocktail bar restaurants with happy hour specials in Key West. Top picks include Bar 1, General Horseplay, The Roost.

What kind of cocktail bar food specials are available during happy hour?

Cocktail Bar restaurants in Key West typically offer discounted appetizers, tacos, small plates, and specialty items during happy hour, often at 30-50% off regular prices.

What time is happy hour at cocktail bar restaurants in Key West?

Most cocktail bar restaurants in Key West run happy hour between 3 PM and 7 PM on weekdays. Some offer daily or weekend specials too.

Which Key West happy hours publish their menu with prices?

111 Key West venues on DiscoverHappyHours have a full menu with prices. From this list: The Roost (28 priced items), General Horseplay (151 priced items). Open any venue page for the happy hour, food and drinks menus.