Tag: Key West Festivals and Events

When is the Best Time to Visit Key West?

With constant sunshine, warm weather, and turquoise waters, Key West offers an incredible year-round vacation destination. Deciding the best time to visit Key West depends on your personal preferences and what you want to do during your visit. Whether you are looking to escape the cold or want to enjoy fewer crowds during the slower seasons, Rent Key West Vacations has the perfect property waiting for you!

Winter (December-March)

Month High / Low (°F)

December 77° / 70°

January 75° / 67°

February 76° / 68

  Photo: The Florida Keys & Key West

Winter is the most popular time to visit Key West, attracting snowbirds from around the world looking to escape the cold. The average winter high is a beautiful 75 degrees and the low temperatures usually only fluctuate down 10 degrees, and winter offers minimal rainfall. Celebrate the holidays in Key West with annual events like the Key West Holiday Parade, Lighted Boat Parade, and New Year’s Eve at various countdowns and celebrations around the island. Discover more information about Events Welcoming the New Year with Rent Key West Vacations!

Keep in mind that the influx of tourists also makes this the most expensive season to plan your visit. Accommodations, tours, and experiences fill up fast in the peak season. Advanced reservations are highly recommended during our winter season of perpetual summer. 

People from around the globe descend upon the island in January for delicious delectables during the internationally acclaimed Key West Food and Wine Festival. January also gathers a multitude of readers and writers for the Key West Literary Seminar which always garners the highest reviews! In addition to tepid temperatures, February offers the longstanding Old Island Days Arts Festival featuring fine arts and crafts at events, galleries and openair street markets.

Spring (March-June)

Month High / Low (°F)

March 78° / 70°

April 82 ° / 74°

May 85° / 77°

Spring is a beautiful season to visit Key West, with warmer weather, and fewer crowds than the winter. The exception to this is spring break, usually around March, when many families, young professionals and some college students plan their visits. Spring is a popular time for swimming, fishing, snorkeling, visiting gardens, and wildlife watching. St. Patrick’s Day in Key West offers a myriad of activities from bar strolls, 5 & 10K walk/runs, to themed boat excursions and more.

A visit during April or May enables you to enjoy all your favorite activities without the spring break crowds! The annual Conch Republic Independence Celebration at the end of April offers a fun glimpse into how “Key West Seceded Where Others Have Failed”. Learn more about planning your Spring Getaway in Key West.

Summer (June-September)

Month High / Low (°F)

June 88° / 80°7 days

July 90° / 81°8 days

August 91° / 81°10 days

Key West summer is the hottest time of the year and the start of hurricane season, so be prepared for the possibility of some passing rain showers. Summer is the second most popular time to visit Key West, welcoming an influx of families enjoying school breaks. Water is at its clearest and warmest in the summer, ideal for swimming, snorkeling, and diving. 

Summer is the best time to visit Key West for travelers who want to join us for festivals! Key West Pride and MangoFest both occur in June. July 4th includes the traditional fireworks, festivities and The Mermaid and Key Lime Festivals; and Hemingway Days later in the month. Also, the very popular  Lobsterfest is held in August. 

Fall (September-November)

Month High / Low (°F)

September 89° / 80°

October 85° / 78°

November 79° / 72°

Photo: Tripadvisor

Fall is the low season in Key West and the best time to visit for travelers looking for fewer crowds, lower priced accommodations, and travel incentive flight pricing. The beginning of September offers the annual Key West BrewFest with tastings and pairings on the beach and at venues around the island.  The island also welcomes thousands of women for the event-packed annual WomenFest!   Fantasy Fest is at the end of October and is the most popular fall event, welcoming up to 75,000 travelers each year! Join us for ten days of costumes, parades, libations, and excitement this October!

November kicks off with the Race World Offshore Key West Championships featuring the world’s top power boat racers vying for the prestigious title, prizes and more.  Each November, also attracts film aficionados to the island for the highly praised Key West Film Festival. It always receives two thumbs up!

We all have a lot to be thankful for on this island of Key West, especially all of us who are fortunate enough to be able to celebrate Thanksgiving here in paradise.  Plan a Thanksgiving getaway with Rent Key West Vacations and celebrate the holiday island style!

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Rent Key West Vacations

So, when is the best time to visit Key West? Anytime! Rent Key West Vacations offers excellent rental properties to host your getaway year-round. Browse over 60 Key West vacation rentals and let our knowledgeable staff help you customize your vacation. Please call our reservation specialists at 1-800-833-7368 for more information!

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.

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