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)
8
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)
9
Schooner Wharf Bar
Bar & grill
Longtime open-air hangout for seafood complemented by live music & dockside views.
$$ $$
4.50 (4.2K reviews)
10
Banana Cafe
French restaurant
French bistro, popular for breakfast, serving crêpes & other easygoing fare in a low-key setting.
$$ $$
4.50 (4K reviews)
12
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
Southernmost Beach Resort
Resort hotel
Refined rooms at a colonial-style retreat with 3 pools & lawn games, plus a private pier & beach.
4.20 (3.3K reviews)
15
Pepe's Cafe
American restaurant
Rustic joint with laid-back vibes dishing up signature breakfasts plus surf 'n' turf since 1909.
$ $$$
4.50 (3K reviews)
16
Moondog Cafe
Restaurant
Relaxed garden cottage offering separate menus for breakfast or lunch & dinner, as well as drinks.
$$ $$
4.60 (2.7K reviews)
17
Key Lime Pie Bakery
Pie shop
Charming outfit offering fresh-baked pies, whole & by the slice, plus local souvenirs & gifts.
$ $$$
4.40 (2.3K 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)
20
Louie's Backyard
Restaurant
Revered, longtime eatery offering Caribbean-American cuisine, ocean views & a wine bar.
$$$ $
4.50 (2.1K reviews)