1
Bert's Bar
Bar
👍👍 Quaint, understated bar on Key West’s historical Duval street. As unassuming as it is unpretentious, Bert’s Bar truly encapsulates the finest Key West has to offer - good beer and better bros
5.00 (62 reviews)
2
Uva Wine Shoppe
Wine store
Small batch wines pair with light bites at this inviting wine shop, also offering classes.
4.90 (98 reviews)
3
Joe's Tap Room
Bar
Offshoot of adjacent Sloppy Joe's Bar, featuring sports on TV & various craft beers in compact digs.
4.90 (34 reviews)
4
Speakeasy Inn & Rum Bar
Hotel
Bright suites with kitchenettes in a 19th-century inn offering a cocktail bar & a wraparound porch.
4.80 (277 reviews)
5
Heroes Bar and Liberty Lounge
Live music bar
👍👍 Very chill atmosphere on a Sunday. Happy hour is daily 12 to 6. We love an early happy hour. It is also a very long happy hour as well. 6 hour happy hour. Love the murals on the wall. Plenty of honor on the walls. Love all the contributions from my fellow veterans. I now feel compelled to add some o...
$ $$$
4.80 (262 reviews)
6
Kava Culture Kava Bar
Lounge
👍👍 My new favorite spot! Thank you Kate for being great. Love the atmosphere and welcoming energy.
$$ $$
4.80 (152 reviews)
7
The Retro Room
Beer hall
👍👍 If you're wondering why they have a 5 star rating, it's because this bar serves up nostalgia with every single drink. With over 20 beers on tap, there's a lot to choose from.
There is no other place in Key West that has taken me back in time to my 12 year old self than The Retro Room, and I would dr...
4.80 (138 reviews)
8
22&Co
Bar
👍👍 Such a great time spent in this small yet cosy, friendly bar.
The bartender was super nice, easy to talk to and we finished talking with other nice customers all around.
The drinks are really good ! Special rating to the classic Margarita, excellent and with a pretty large drink !
4.80 (108 reviews)
9
Santiago's Bodega
Tapas restaurant
Charming tapas bar pairing global small plates with house-specialty sangria in a warm room.
$$ $$
4.70 (2.6K reviews)
10
The Rum Bar
Bar
Snug watering hole featuring a vast rum menu in a relaxed setting with a small patio.
$$ $$
4.70 (907 reviews)
11
The Flaming Buoy Filet Co.
New American restaurant
Steak & seafood spot serves an artful New American menu & daily specials in a funky tropical space.
$$ $$
4.70 (812 reviews)
12
General Horseplay
Cocktail bar
Easygoing bar offering a diverse menu of cocktails, plus cupcake sushi & familiar snacks.
$$ $$
4.70 (470 reviews)
14
Funky Rooster Coffee House & Wine Bar
Coffee shop
👍👍 Awesome Coffee Shop!!! The staff is kindhearted and selfless. The coffee is delicious. The interior is decorated well. There’s indoor and outdoor seating. Going to Funky Rooster is more than a pleasure; it’s a great opportunity!!!!
4.70 (364 reviews)
15
Little Room Jazz Club
Jazz club
Cozy, homey music venue presenting nightly live jazz with craft beer, cocktails & light snacks.
$$ $$
4.70 (309 reviews)
16
Vinos on Duval
Wine bar
👍👍 Almost always end up at Vinos when in Key West. I love the indoor decor, the staff is super friendly and for the bubbles lovers they have the best Champagne deal in town. And nothing better than sipping some bubbles on Duval while doing some people watching...
$$ $$
4.70 (291 reviews)
17
The Roost
Cocktail bar
😠 Great is Gruppy. Awesome knows drinks, went back again bartender Annette is awful. Rude, drunk, taking shots, ran patriots off, couldn't ' get orders right , very sad. Hope she doesn't ruin a great business. Get rid of Annette. Terrible at making drinks & didn't get our drinks right. Worst bar ten...
$$ $$
4.70 (255 reviews)
18
Shots & Giggles
Bar
Low-key, intimate bar attracting locals with 60+ craft beers, wine, spirits & sports on TV.
$$ $$
4.70 (247 reviews)
19
Chart Room Cocktail Lounge
Cocktail bar
👍 Only in Key West. A dive bar with a resort built around it. Have not stayed at the Pier House Resort, but the Chart Room is definitely worth a visit. Very old school KW, surrounded by very new school KW. This is where Jimmy Buffett 1st stopped upon arriving in KW (allegedly) and played for the likes...
4.70 (174 reviews)
20
VIV Wine Bistro
Bistro
Popular, arty wine bar with 20+ wines by the glass & 200+ bottles, plus cheeses & charcuterie.
$$ $$
4.70 (142 reviews)