Key West Events

Vacation Homes of Key West brings you an updated calendar of Key West Events to help you plan the trip you are dreaming about. Choosing a vacation rental property from Vacation Homes of Key West will provide you with a beautiful, and usually the most affordable place to stay for your favorite Key West events. If you are planning to come to the island for a more popular event, such as Fantasy Fest or New Years, we suggest you reserve your vacation rental well in advance so you don't miss out on your favorite place to stay.

January 2016

Key West Outdoor Movies

Jan 15 to May 20

Enjoy free-admission outdoor movies at Bayview Park every first and third Friday through May 20th. Starts at dusk. Bring lawn chair, snack and refreshments. Check website for upcoming movie events.

February 2016

Red Barn Theatre Presents: Buyer and Cellar

Feb 8 to Mar 12

The Red Barn Theatre has been presenting professional theater in Key West for 36 years, at 319 Duval St. (rear), Key West. Treat yourself to this smash hit comedy from New York, written by Jonathan Tolins. Buy tickets now on-line or call 305-296-9911

Key West Theater presents: Winter Concert Series

Feb 20

Featured performer is Robert Randolph and the Family Band, his accompanists, with Caffeine Carl. Randolph calls his "thing" really upbeat, uptempo, with great guitar riffs. Key West Theater located at 512 Eaton Street. Tickets available online.

March 2016

March Merkin Permit Tournament

Mar 14 to Mar 17

A charity flats-and-fly-only tournament with a twist - in addition to catch and release, anglers earn extra points for tagging their caught fish. Held at the Key West Harbour Yacht Club on Stock Island.

April 2016

Third Annual Cow Key Channel Bridge Run

Apr 10

Feel like running across a bridge in the Florida Keys without waking up early or breaking a sweat? Join zany-dressed participants for the world's only Zero K across one of the shortest bridges in the Keys. The event is free to watch.

Conch Republic Brew Days

Apr 24

The Key West Artisan Market is a vibrant, open air bazaar filled with artists, authors, chef-made cuisine, craftspeople, performers, fresh produce, baked goods, cheeses and flowers, craft beer

June 2016

VFW Fishing Tournament

Jun 11

This family oriented tournament offers cash prizes for dolphin, wahoo, tuna, snapper and grouper, along with prizes for heaviest fish by a lady angler, heaviest fish by a juvenile angler, pee-wee and active service member. Heaviest Dolphin is worth $2,500. All proceeds benefit disabled and/or needy veterans in Monroe County.

July 2016

Fourth Annual Key Lime Festival

Jul 2 to Jul 4

A wacky talent show, pie-eating and cooking contests and other tasty temptations await Key West visitors during the fourth annual Key Lime Festival. A Key Lime Martini and Margarita Sip and Stroll will kickoff the weekend-long event.

4th of July Fireworks

Jul 4

A fabulous fireworks show staged off the Key West White Street Pier. There is something especially magical about fireworks launched over the ocean. Best place to watch is near the pier at Higgs Beach, or anywhere nearby the water along the south end of the island. This annual event is sponsored by the Key West Rotary Club.

Del Brown Permit Tournament

Jul 9 to Jul 12

Anglers fly-fish on the flats in a challenge that honors the late angling pioneer Del Brown, who caught and released more than 500 permit off the Keys. Professionals and guides are allowed to compete as well.

August 2016

Key West Lobster Fest

Aug 11 to Aug 14

When it comes to lobsters, Key West throws one of the best crustacean parties you can imagine. Every year the island celebrates the opening of lobster season with a big gathering for four days and nights. Street fair, free concert, vintner's dinner, lobster brunch, Duval Crawl, to name a few of the highlights. Great time of year to visit Key West when the water is perfect, and the vacation rental rates are at their lowest.

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