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September 16th
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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

45th Annual Swim Around Key West

Jun 12

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.

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.

Key West Caribbean Carnival

Jun 18 to Jun 19

Key West Caribbean style Carnival is a weekend of entertainment, island food, dance and a costumed parade through the streets of Old Town. The event will take place at the Coffee Butler Amphitheater.

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.


July 2021

2nd Annual Mermaid Festival

Jul 1 to Jul 5

The Key West Mermaid Festival was founded by a Key West native mermaid, and local mermaid boutique owner. She, along with her drew and pod, invite you to step back in time to an island called Cayo Hueso (Bone Cay), where the Gulf meets the Atlantic, and the captains, seafarers, and fishermen would tell their stories of the sweet sirens' songs.

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.

Hemingway Days

Jul 20 to Jul 25

The annual celebration of the legendary author’s work and lifestyle features literary readings, the Running of the Bulls, a short story competition, fishing tournament, 5k Run and Paddleboard Race, Sloppy Joe’s Look-Alike Contest and a birthday “party” commemorating Ernest’s July 21st birthday.

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.

25th Annual Key West Lobsterfest

Aug 12 to Aug 15

The Florida Key lobster season opens Aug. 6th. Every year for 25 years seafood lovers gather here to devour tasty lobster dishes served in several ways including a traditional lobster boil. Join us for all the festivities and the street fair featuring, of course, the sweet, decadent lobster.

Paula Poundstone

Aug 21

Comedian - At Key West Theater


September 2021

Womenfest Key West

Sep 1 to Sep 5

Key West has always been known for our acceptance of the LBGQT community. This event is for lesbians and their friends, either single, couples or groups to get together to experience a city where openness and acceptance has made us famous throughout the world.

Key West BrewFest

Sep 2 to Sep 6

This event is arranged by the Key West Sunshine Rotary. It is a multi-day festival that includes, beer pairing dinners, pool parties and other activities around town. The weekend will conclude with our signature tasting event.

Key West Film Festival

Sep 17 to Sep 21

This years festival will showcase films that showcase excellence in storytelling. The screenings will be at Tropic Cinema at 416 Eaton St. The films will be from different genres and categories. There will be multiple events over the four days that will include social events with filmmakers, actors and film lovers. Please see the website for more information.

Key West Musicians Festival

Sep 18 to Sep 19

This is the 10th Annual Key West Musicians Festival at the Smokin' Tuna Saloon. This is a FREE two day event that features many local musicians and songwriters. They will be taking up donations to benefit a local charity; Sister Season Fund. Please visit the website for more information.

Fort Taylor Living History Weekend

Sep 18 to Sep 19

Join us at the Historic Fort Zachary Taylor State Park for a weekend of a Living History Weekend. Our re-enactors will be setting up tents, cleaning their weapons and firing up the blacksmith shop to give the guests a glimpse into the past. There will be tours available and public interaction is encouraged! There is a fee to enter the park. Check out the website for more information.

Cars & Coffee

Sep 19

Here is a great event for the whole family! Come to Denny's at 2710 North Roosevelt Blvd. between 8am - 11pm to see our local vintage and sports cars. If you are just visiting and just happened to bring your vintage or sportscar to town, bring it on over.. everyone and every car is welcome.

Good Vibes Summer Tour

Sep 19

Live concert at the Coffee Butler Amphitheater. Featuring Rebelution, Steel Pulse and The Green. Event starts at 5:00pm. Check out the website for further details.

Cartel Baggers Key West Run

Sep 24 to Sep 26

Join us for a great weekend at The Opal Key Resort for a great time! This event is to benefit The American Cancer Society. Please check out the website for more information.

Gold Coast Comedy Tour

Sep 26

Get your laughs at the Comedy Key West on September 26th! There will be three AMAZING performers there from Riley Edwards, Nik Macik and Connie Fernandez!! Please click on the link for more information.


October 2021

Rocky Horror Picture Show

Oct 2

Come watch one the most loved (or hated) movies of our time...The Rocky Horror Picture Show. It will be showing ONLY on Oct. 2nd at 7pm at Tropic Cinema at 416 Eaton St. See website for more information.

Concert - Brett Eldredge

Oct 2

Brett Eldredge is coming to Key West!! Get your tickets now before it's too late!!! See website for more information and to get tickets!

Concert - ZOSO

Oct 13

The Ultimate Led Zeppelin Experience. Come to the Sunset Pier on Oct. 13 at 6pm to see ZOSO put on a concert in honor of Led Zeppelin. This concert is part of the Sunset Pier Benefit Concert Series. Please click on the link for tickets and more information.

Green Fairy Fest

Oct 15 to Oct 17

Come join the fun at the Green Fairy Fest that will be at The Gates Hotel. There will be 10 top national 3D body painting artists in attendance. Please see website for more information.

Concert - Badfish

Oct 19

Come see BADFISH live at the Sunset Pier on Oct. 19th from 3pm - 7pm for a tribute to SUBLIME. This concert is part of the Sunset Pier Benefit Concert Series. Click on the link for tickets and more information.

Fantasy Fest

Oct 22 to Oct 31

This a a NOT TO MISS event here in Key West. A 10 day event where we have costumes, masquerade competitions, street fairs, promenades a lavish parade with not to miss floats! This year's theme will be "All a Daze for a Holliday!"

Concert - That Arena Rock Show

Oct 23

Join us at the Sunset Pier on Saturday, October 23rd from 6pm - 9pm for a Tribute to some of our favorite 70's and 80's rock bands. Take a trip back in time with covers from some of your favorite bands like: Led Zeppelin, Aerosmith, AC/DC, Bon Jovi, Guns N Roses and many others. This is a FREE concert!!! Check out the website for more information.


November 2021

Parrot Heads / Meeting of the Minds

Nov 3 to Nov 9

If you are a Jimmy Buffett fan, this is an event you do not want to miss! This is a muli-night event that will have a variety of social event, music on the beach each night and food and beverages that you can buy at your leisure. This is an event that the entire island participates in! Come join the fun!!

Jimmy Buffett @ Margarittaville

Nov 3

Jimmy Buffett will be performing live, on stage at the Key West Margaritaville. This is the first time in a long time he has announced that he will be here! This is part of the Parrot Heads/Meeting of the Minds festivities. Come join the fun!


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