pinterest facebook instagram twitter youtube google my business
  • (305) 294-7358
Key West Time
October 3rd
6:37am · 81°F

2023 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 2023

Key West Food & Wine Festival

Jan 25 to Jan 29

The Key West Food and Wine Festival is a series of themed culinary events showcasing diverse wines and creative cuisines. Join us for this 14th annual festival with over 20 unique venues.

February 2023

Super Bowl Beach Party

Feb 12

Watch The Big Game with the best beach view. Casa Marina 5:00 pm

Old Island Days Art Festival

Feb 25 to Feb 26

Fine Art lovers will enjoy creative offerings from over 100 artists. This open-air show takes place at Key West Truman Waterfront Park, from 10 am to 5 pm.

March 2023

Anne Mckee Artist Fund Fine Art Auction

Mar 12

The Anne McKee Artists Fund (AMAF) was established in 1992 after its founder, Anne McKee, saw a pressing need to assist individual artists from Key West. Now, after more than 30 years, this non-profit organization supports an array of visual, literary & performance artists whose creative contribution adds to the quality of life throughout the Florida Keys

April 2023

Conch Republic Independence Celebration

Apr 14 to Apr 23

Celebrate 41 years of the Conch Republic. This is an annual event honoring Key West's quirkiness with silly events. Declare your Fun-dependence with humor and become part of Key West's One Human Family.

May 2023

Key West Song Writer's Festival 2023

May 3 to May 7

The largest singer-songwriter festival of it's kind in the World. Join us for 5 days of live music from up and coming performers and well known artist. This event takes place at some of the island's most popular Beaches, Boats, Bars, Resorts and Historic Theatres.

June 2023

Key West Pride 2023

Jun 7 to Jun 11

Celebrate PRIDE in Paradise. Key West is known for it's open and accepting atmosphere which makes the island so special. Join the party and experience the island's One Human Family philosophy.

Annual Swim Around Key West

Jun 17

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.

10th Annual VFW Fishing Tournament

Jun 18 to Jun 20

A family fun tournament with cash prizes!

Mango Fest Key West

Jun 22 to Jun 25

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 2023

Key West Marlin Tournament

Jul 19 to Jul 22

Hosted by the Stock Island Marina & Village with nightly festivities leading up to an awards banquet.

August 2023

Tropical Heat

Aug 9 to Aug 13

The Key West Business Guild presents this all-male celebration that typically includes pool and dance parties, on-the-water adventures and a fashion show.

September 2023

Key West Womenfest

Sep 6 to Sep 10

Womenfest has a simple goal: to celebrate ALL women! Key West Womenfest offers a wide range of activities for those who want to socialize, feel comfortable being themselves, soak up some sun, then party and dance the night away.

October 2023

Fantasy Fest

Oct 20 to Oct 29

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 "Uniforms & Unicorns- 200 Years of Sailing into Fantasy""

November 2023

Race World Offshore World Championship

Nov 5 to Nov 12

The World's best offshore power boat teams compete for the championship in Key West Harbor.

Key West Film Festival

Nov 15 to Nov 19

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.

Sort Properties

Rental Period

Vacation Rental

Rentals For
Social Distancing

rentals for social distancing

Sunset Key

sunset key






town houses and condos







Truman Annex

truman annex