Entertainment & Events in Key West, Florida

Special Events

Southernmost Scavenger Hunt 305-292-9994
The Southernmost Scavenger Hunt offers a wide variety of custom designed scavenger hunts. more
Sunset Celebration 305-292-7700
P.O. Box 4837
Key West, FL 33040
A nightly arts festival at Mallory Square Dock in Key West, Florida, Sunset Celebration features arts and crafts exhibitors, street performers, food carts, psychics and much more. more

Cinema

Regal Cinema Key West 6 305-294-0000
3338 North Roosevelt Boulevard
Key West, FL 33040
This comfortable cinema features first-run Hollywood movies and critically-acclaimed films plus offers a large concession stand. more

Night Life

Sloppy Joe's 305-294-5717
201 Duval Street
Key West, FL 33040
Your visit to Key West would not be complete if you did not stop at this internationally known bar that has been offering satisfying large drinks and continuous live entertainment since 1933. Their world famous retail shop is also on site that offers over 300 souvenirs. more
Hog's Breath Saloon 305-296-4222
400 Front Street
Key West, FL 33040
Renowned for food and fun, this place invites all to stop in and enjoy outdoor dining, a raw bar, their famous T-shirts, and exciting live entertainment. more
Bull & Whistle Complex 305-296-4565
427 Caroline Street
Key West, FL 33040
Located in Historic Old Town
One of the last open air bars in the area, this complex has been offering local excitement and entertainment since 1912 and features some of the finest entertainment in town. more
Green Parrot Bar 305-294-6133
601 Whitehead Street
Key West, FL 33040
Since 1890, this open-air tropical bar has been a Key West landmark and has become renowned as the home of great drinks. Enjoy outstanding live entertainment on the weekends and have fun playing pool, darts, or pinball every day of the week. more
Schooner Wharf Bar 305-292-9520
202 William Street
Key West, FL 33040
Located on the Historic Harbor Walk
Consistently voted as being the "Best Locals Bar" in Key West, this not-to-be-missed watering hole has been written up in many national publications and has been visited by numerous celebrities. Local seafood delicacies are served here and music and live entertainment are featured throughout the week. more
Rick's & Durty Harry's Entertainment Complex 305-296-4890
202 Duval Street
Key West, FL 33040
Rick's Bar, Durty Harry’s Key West, Rick’s Tree Bar, the Red Garter Saloon, Rick’s Upstairs, Rick’s Mardi Gras, Rick's Loft and the Crow’s Nest are featured at Rick's & Durty Harry's Entertainment Complex in Key West, Florida. more

Concerts & Performances

Tennessee Williams Theatre, The 305-296-1520
5901 College Road
Key West, FL 33040
The largest professional performing arts venue in the Florida Keys, this complex features a spacious Grand Foyer, a 20 foot movie screen, a 480 seat theater house, and a 40 foot proscenium stage. A wide range of music, dance, and theatrical performances are held here. more

Plays & Productions

Waterfront Playhouse 305-294-5015
310 Wall Street
Key West, FL 33040
Located in Mallory Square
"The oldest continually running theatre group in Florida," this theatre is located in a mid-1850s wrecker's warehouse and presents entertainment dramas and comedy performances from December to June. more
Red Barn Theatre, The 305-296-9911 (Box Office)
319 Duval Street (Rear)
Key West, FL 33040
This small professional theater group has been performing highly entertaining dramas, musicals, and comedies, including works by new playwrights, for over 30 years. more

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