Annual Key West Festivals & Events Guide

As one of the longest-standing and most trusted vacation rental companies in Key West, we are proud to be your local experts during your Key West getaway. Rent Key West Vacations’ knowledgeable staff is here to introduce you to the best Key West festivals and events our beautiful island has to offer! Keep up to date with local happenings on our Events page and plan your Key West vacation around one of our exciting annual festivals. No matter when you decide to visit us, our beautiful Key West Vacation Rentals offer the perfect homebase to enjoy events on the island!

January: Key West Food and Wine Festival

Escape the cold this winter and dive into the warmth of our unique culinary scene during the Food and Wine Festival. This festival includes over 20 special events, including wine tastings, innovative culinary creations, and chef collaborations. 

February: 58th Old Island Art Festival

This is an artistic Key West tradition not to be missed!  Thousands of original pieces of artisan made arts and crafts will be displayed and available for purchase.  This is the perfect opportunity to bring home a piece of paradise!

March to April: Key West Spring Break

Some students, young professionals, working grown-ups and retirees recoup and rejuvenate on the beaches and around the island of Key West!  Please come take a break with us this Spring!  

April: Conch Republic Independence Celebration

Celebrate the founding of the Conch Republic and the brief secession of the FL Keys from the United States. This ten-day festival features parades, reenactments, art fairs, bar crawls, costume contests, drag (Queen) races, bed and boat races, and even more fun in the Conch Republic. 

May: Key West Songwriters Festival

This Key West Festival is the largest of its kind in the world! Experience five days of live music with over 150 performers during the Songwriters Festival.  From intimate gatherings to large concerts, there is something for every music aficionado at this annual festival.  

June: Key West Pride Week

Key West is known worldwide for being an LGBTQ+ friendly destination, and we invite you to spend pride month on our tropical island! Pride Week will be full of events like parades, pool parties, drag shows, talent shows, fun nightlife, sunset sails, and diverse entertainment! 

July: Key Lime Festival, Key West Mermaid Festival, July 4th Celebrations and Hemingway Days!

Plan your vacation around the 4th of July and join Key West’s Independence Day parties and fireworks.  The Key Key Lime & Mermaid Celebrations also happen during the long weekend holiday. Later in the month, plan your getaway around Hemingway Days and celebrate the author with look-alike contests, poetry readings, imbibing and fishing tournaments.

August: Key West Lobsterfest

Visit Key West during the opening of lobster season and join the biggest party of the summer with mouthwatering lobster dishes, live music, and refreshing drinks.  Folks from around the world will enjoy Florida spiny lobster on Duval Street, beaches, poolside and in most of Key West’s excellent dining establishments.  

September: Key West Womenfest and Key West BrewFest

This famous global event invites all women to celebrate their gender.  Lesbians, straights, trans and allies gather to socialize, soak up the sun, and dance the night away with fellow like-minded women and their friends!  Beer lovers can enjoy Key West craft beers which are celebrated during BrewFest each year with this festival celebrating all things grain, hops and fun!

October: Goombay Caribbean Festival & Key West Fantasy Fest

Fantasy Fest is the biggest annual event in Key West, attracting over 75,000 visitors each year! This ten-day festival features parades,costumes, competitions, and parties.  Come early for the pre-festival, Goombay Caribbean Festival.  It runs the weekend before the start of Fantasy Fest and is full of great food, music and culture on the streets of Bahama Village in old town Key West. 

November: Key West Film Festival and Thanksgiving on the Island of Key West

This Film Fest has become world renowned and is part of the beginning of the annual awards circuit!  Of course, there is nowhere better to be grateful during Thanksgiving than Key West, so please join us at our bountiful, island table!

December: Key West Holiday Events & New Year Celebrations!

Visit Key West for the holidays and enjoy seasonal activities, including parades, concerts, Santa visits, festivals, light displays, fun on the water, and much more!  And, nothing beats ringing in the New Year on the island of Key West.  We drop drag queens, giant conch shells, pirate wenches and have all types of parties and celebrations!

Stay in Our Key West Vacation Rentals

There is always something happening on our slice of paradise; plan your getaway around one of our Key West festivals today! Whether you are looking for a Key West vacation rental near the beach or in the historic district, Rent Key West Vacations has you covered! To customize your Key West vacation, please call our reservation specialists at 1-800-833-7368.