1
Sloppy Joe's Bar
Bar
Open since 1933, this bar offers live music & dancing plus a separate tap room for sports-watching.
$$ $$
4.50 (12.5K reviews)
3
Blue Heaven
American restaurant
Iconic landmark for Floridian-Caribbean cuisine & key lime pie, with a funky setting.
$$ $$
4.60 (9.2K reviews)
4
Two Friends Patio Restaurant
American restaurant
Long-standing mostly outdoor cafe with an old-school American menu plus lively karaoke.
$$ $$
4.50 (5.8K reviews)
5
Hog's Breath Saloon
Pub
Popular pub providing bar food on a covered outdoor patio plus live music & dancing.
$$ $$
4.50 (4.7K reviews)
6
Margaritaville - Key West
American restaurant
Lively joint offers island-inspired fare & margaritas plus a gift shop & live music most nights.
$$ $$
4.20 (4.6K reviews)
7
Irish Kevin's
Irish pub
Lively Irish pub with nightly music, an expansive stout list & an eclectic pub-grub menu.
$$ $$
4.60 (4.5K reviews)
9
Caroline's Cafe
American restaurant
American cafe serving po' boys, conch fritters & the like in a circa-1838 house with outdoor seats.
$$ $$
4.50 (4.2K reviews)
10
Schooner Wharf Bar
Bar & grill
Longtime open-air hangout for seafood complemented by live music & dockside views.
$$ $$
4.50 (4.2K reviews)
11
Half Shell Raw Bar
Seafood restaurant
Casual fish house with picnic tables & waterside seating in a former shrimp-packing facility.
$$ $$
4.40 (4K reviews)
12
Green Parrot Bar
Bar
An institution since 1890, this watering hole features a jukebox & frequent live music.
$$ $$
4.60 (4K reviews)
13
Hard Rock Cafe
American restaurant
Rock ’n’ roll-themed chain with a high-energy vibe serving burgers & American classics.
$$ $$
4.30 (3.9K reviews)
14
The Stoned Crab
Seafood restaurant
Open-air, dockside spot at Ibis Bay Beach Resort with local seafood specialties & organic cocktails.
$$$ $
3.50 (3.5K reviews)
15
Fogarty's
American restaurant
Casual bar & grill offering American fare & local seafood, plus a variety of frozen drinks.
$$ $$
4.50 (3.4K reviews)
16
Sunset Pier
Seafood restaurant
Relaxed dockside seafood eatery at the Ocean Key Resort & Spa with water views, drinks & live music.
$$ $$
4.60 (3K reviews)
17
Rams Head Southernmost
Breakfast restaurant
Vibrant open-air bar with patio seating, offering seafood, sandwiches, and cocktails, plus live music.
$$ $$
4.50 (2.9K reviews)
18
Pinchers
Seafood restaurant
Local seafood shack chain known for its crab dishes, fried fish & other shore favorites.
$$ $$
4.20 (2.8K reviews)
19
Willie T's
Bar
Festive hangout for tropical drinks & Florida-inspired American eats in a mostly outdoor setting.
$$ $$
4.50 (2.7K reviews)
20
Santiago's Bodega
Tapas restaurant
Charming tapas bar pairing global small plates with house-specialty sangria in a warm room.
$$ $$
4.70 (2.6K reviews)