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
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)
4
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)
5
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)
6
Hard Rock Cafe
American restaurant
Rock ānā roll-themed chain with a high-energy vibe serving burgers & American classics.
$$ $$
4.30 (3.9K reviews)
7
Fogarty's
American restaurant
Casual bar & grill offering American fare & local seafood, plus a variety of frozen drinks.
$$ $$
4.50 (3.4K reviews)
8
Pepe's Cafe
American restaurant
Rustic joint with laid-back vibes dishing up signature breakfasts plus surf 'n' turf since 1909.
$ $$$
4.50 (3K reviews)
9
Harpoon Harry's
American restaurant
Cash-only diner offering hearty American comfort food in a cheerful atmosphere with quirky accents.
$ $$$
4.70 (2.8K reviews)
10
Garbo's Grill @ Hanks!
Restaurant
Tiny, husband-&-wife-run food stand serving eclectic, inventive takes on tacos, burritos & burgers.
$$ $$
4.70 (2.6K reviews)
11
Latitudes
Restaurant
Upscale restaurant with sea views, outdoor dining & a menu of contemporary cuisine.
$$$$
4.60 (2.5K reviews)
12
Denny's
Diner
Casual diner chain dishing up classic American comfort fare, including all-day breakfast favorites.
$ $$$
4.10 (2.5K reviews)
14
Bagatelle
Seafood restaurant
Seafood-focused American eatery set in an 1884 house with wraparound balconies for people-watching.
$$ $$
4.50 (2.2K reviews)
15
Outback Steakhouse
Steak house
Boisterous Australian-themed chain serving steaks, seafood & other hearty steakhouse fare.
$$ $$
4.10 (2.1K reviews)
16
Jack Flats
American restaurant
Laid-back venue with a long bar & booths offering home-style surf 'n' turf plus sports on TV.
$$ $$
4.50 (2K reviews)
17
IHOP
Breakfast restaurant
Long-standing chain serving a wide variety of pancakes & other American breakfast & diner fare.
$ $$$
3.80 (2K reviews)
18
Smokin' Tuna Saloon
Restaurant
Bustling, open-air hangout featuring 2 bars, local seafood & live music on the courtyard stage.
$$ $$
4.60 (1.9K reviews)
19
Salute! On The Beach
American restaurant
Funky open-air restaurant right off the sand featuring fish-focused Italian fare & ocean views.
$$ $$
4.40 (1.8K reviews)
20
Island Dogs Bar
Bar
Burgers, wings & oysters, plus tropical martinis & live music in casual digs with outdoor seats.
$$ $$
4.30 (1.7K reviews)