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.
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.
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
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.
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.
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.
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.
A family fun tournament with cash prizes!
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.
Hosted by the Stock Island Marina & Village with nightly festivities leading up to an awards banquet.
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.
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.
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""
The World's best offshore power boat teams compete for the championship in Key West Harbor.
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.