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)
2
Blue Heaven
American restaurant
Iconic landmark for Floridian-Caribbean cuisine & key lime pie, with a funky setting.
$$ $$
4.60 (9.2K reviews)
3
Smathers Beach
Public beach
Public beach & a spring break destination with showers & volleyball, plus jet ski rentals.
4.20 (8K 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)
6
Hog's Breath Saloon
Pub
Popular pub providing bar food on a covered outdoor patio plus live music & dancing.
$$ $$
4.50 (4.7K reviews)
7
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)
8
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)
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
Sunset Pier
Seafood restaurant
Relaxed dockside seafood eatery at the Ocean Key Resort & Spa with water views, drinks & live music.
$$ $$
4.60 (3K reviews)
14
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)
15
Willie T's
Bar
Festive hangout for tropical drinks & Florida-inspired American eats in a mostly outdoor setting.
$$ $$
4.50 (2.7K reviews)
16
Garbo's Grill @ Hanks!
Restaurant
Tiny, husband-&-wife-run food stand serving eclectic, inventive takes on tacos, burritos & burgers.
$$ $$
4.70 (2.6K reviews)
17
Alonzo's Oyster Bar
Seafood restaurant
Waterfront restaurant offering a chill vibe, seafood-centric menu & full bar with daily happy hour.
$$ $$
4.30 (2.2K reviews)
18
Amigos Tortilla Bar
Mexican restaurant
Hopping hot spot with Day of the Dead decor & a menu of Mexican street food & gluten-free beers.
$$ $$
4.40 (2.2K reviews)
19
Bagatelle
Seafood restaurant
Seafood-focused American eatery set in an 1884 house with wraparound balconies for people-watching.
$$ $$
4.50 (2.2K reviews)
20
Louie's Backyard
Restaurant
Revered, longtime eatery offering Caribbean-American cuisine, ocean views & a wine bar.
$$$ $
4.50 (2.1K reviews)