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April 19th
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2021 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 2021

Key West Kingfish Mayhem

Jan 14 to Jan 17

The 1st of 4 tournaments in the Kingfish Mayhem Pro Series of fishing competitions. The goal is to catch the largest kingfish in Florida Keys waters.

Key West Home Tours

Jan 15 to Jan 16

The best opportunity to see some of the most unique homes on the island, ranging from exquisite restorations to creative renovations, and interior design that compliments each. The tours are the foundation's largest annual fundraising event where all the proceeds go toward awarding historic grants and scholarships. The number of visitors allowed inside each home will be limited, social distancing and masks will be required, and hand sanitizer will be provided.

Kelly McGillis Classic Flag Football Championship

Jan 19 to Jan 25

International teams of women and girls unite in Key West for adrenaline-charged sports matches and associated activities. The tournament attracts players ranging from 9 years old to seniors who compete in multiple divisions, develop their skills during flag football clinics and enjoy getting to know each other through number of events.

Key West Food and Wine Festival

Jan 27 to Jan 31

The 12th Annual Key West Food and Wine Festival spotlights local chefs, indigenous Florida Keys ingredients, fascinating libations and unique tropical atmosphere! The festival attracts thousands of culinary explorers from around the country who arrive on the tropical island ready to escape the cold winter weather and delight their senses.

Sundance Film Festival at Tropic Cinema

Jan 28 to Feb 3

Tropic Cinema will be creating and hosting Satellite Screen events centered on selections from the 2021 Sundance Film Festival program. Screenings will be held inside the Tropic, as well as outdoors at a variety of venues around Key West.

Master Chef Classic

Jan 31

Chefs from some of Key West's finest restaurants are to present their most creative offerings, competing for first, second, and third-place honors in the appetizer, entree and dessert categories. Attending foodies can enjoy tapas-sized offerings of the entrees and cast people's choice ballots, while official judges determine the dishes most deserving of other awards.


February 2021

Key West Home Tours

Feb 12 to Feb 13

The best opportunity to see some of the most unique homes on the island, ranging from exquisite restorations to creative renovations, and interior design that compliments each. The tours are the foundation's largest annual fundraising event where all the proceeds go toward awarding historic grants and scholarships. The number of visitors allowed inside each home will be limited, social distancing and masks will be required, and hand sanitizer will be provided.


March 2021

March Merkin

Mar 8 to Mar 11

Catching permit on a fly can be hard, but this charity has added a new angle to the fun. This flats-and-fly-only tournament is not only catch and release, anglers earn extra points for tagging their caught fish.

Key West Home Tours

Mar 12 to Mar 13

The best opportunity to see some of the most unique homes on the island, ranging from exquisite restorations to creative renovations, and interior design that compliments each. The tours are the foundation's largest annual fundraising event where all the proceeds go toward awarding historic grants and scholarships. The number of visitors allowed inside each home will be limited, social distancing and masks will be required, and hand sanitizer will be provided.


April 2021

Annual Mile 0 Fest Key West

Apr 27 to May 1

A four-day musical event that combines rock and roll, country, folk, and blues. This incredible event will feature major acts from the "Red Dirt & Americana" genre. All concerts will be held throughout Old Town Key West, the new Truman Waterfront Park Amphitheater, and various bars and clubs on Duval Street.


May 2021

Key West Song Writers Festival

May 5 to May 9

The Key West Songwriters Festival is the largest festival of its kind featuring over 30 shows, 150 performers, and five days of music. This is another one of our favorite events because our guests and visitors have the opportunity to tune in and connect with songwriters and the music in a unique island setting.

Pride Follies

May 22

Pride celebration presented by the Key West Business Guild will take place at the Key West Theater. Fantasy Fest Queen Destiny Montgomery will direct the presentation of Key West talents.

Rams Head Presents: Sammy Hagar & The Circle at Coffee Butler Amphitheater

May 23

One of the rock music's most dynamic supergroups. Show begins at 7:00 pm.


June 2021

VFW Fishing Tournament

Jun 18 to Jun 20

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 $3,000. All proceeds benefit disabled and/or needy veterans in Monroe County.

Mango Fest Key West

Jun 23 to Jun 27

Mango Fest of Key West features all things mango! From tastings to various mango trees and mango daiquiris, this kid-friendly culinary event has so much to offer! Mango Fest Key West is one of the largest fund raisers for the kids in the Police Athletic League.

45th Annual Swim Around Key West

Jun 26

12.5 Mile Endurance Swim Competition presented by Key West Athletic Association. The historic, round-the-island event is the longest-running sporting event in the Florida Keys, founded in 1977. Competition must be completed in 8 hours and typically has 200 participants, including solo and team swimmers.


July 2021

Key Lime Festival

Jul 1 to Jul 5

The Key Lime Festival celebrates all the things that make the Florida Keys unique. Experience a fun, delicious and unforgettable festival while indulging in a vast selection of citrus, limes, a good 'ol pie-eating-contest, good eats and so much more!

Del Brown Permit Tournament

Jul 18 to Jul 21

Dedicated fly anglers and guides can prove their prowess against the elusive Florida Keys permit during the annual Del Brown Permit Tournament. The angler who catches the highest total inches of permit on fly on the flats earns the title of grand champion. Awards also await the grand champion guide, runner-up grand champion and the angler who catches the event's largest permit.

Key West Marlin Tournament

Jul 21 to Jul 24

Anglers targeting marlin and other fish are to compete in guaranteed cash prizes in the Stock Island Marina Village Key West Marlin Tournament. The teams that accumulate the most points for blue marlin, white marlin and spearfish during the tournament's three fishing days are to split a cash prizes.


August 2021

25th Annual Key West Lobsterfest

Aug 12 to Aug 15

Celebrate the opening of lobster season in true Key West fashion. This is a four day event that includes a lobster boil, street fair, bar crawl and free concert! Of course, no event on this island would be complete without something unique. Throughout Key West Lobsterfest, you will see people who love lobster like no other, including people sporting stuffed lobsters as hats! Local restaurants will be showing off their best lobster recipes. Local artists take part in the street fair to show off their best pieces.


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