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February 8th
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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

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.


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