Key West Festivals, Art and Events

Key West opens up for spring, summer, the arts, live shows and more and you're invited to come down to enjoy it all! Our tropical weather is cooperating just fine and our always beautiful Caribbean Sea is sending waves of welcome for repeat guests and newcomers alike. Extend your spring stay on into the summer. You can remote work, learn and play! Enjoy all Key West has to offer and take advantage of our best available rates when you make reservations to stay right on our website or by phone or email with our Vacation Planners. 

Party with your favorite Red-Dirt and Americana bands in Paradise at Mile 0 Fest Key West, April 27th. Where To Stay: Butterfly Cottage - - NEW Nightly Rental, Grand Maison - Nightly Rental

The Key West Songwriters Festival -the largest festival of its kind in the world. Celebrating its 25th year. The festival revolves around five days and nights where live music bliss introduces crowds to the faces, voices and stories behind the songs. May 5-9th 2021. Shows start early afternoon and play into the late night. Where To Stay: My Happy Place - Monthly Rental, Starfish - NEW Monthly Rental

The  innaugural Key West Whiskey Fest food, drink and music festival is one of the most eagerly awaited on  Florida Keys’ busy social calendar. Featuring top-class whiskey,  Popular highlights will include a range of Tastings, Whiskey walks, Workshops, Brunches and plenty more on May 27. Where To Stay: My Happy Place - Monthly Rental, Starfish - NEW Monthly Rental

The 2nd Annual Key West Blues Festival is MAY 29, 2021 - 8:00 PM Ages: 21 & Over Doors Open: 7:00 PM Door Price: $35.00 - $45.00  Where To Stay: My Happy Place - Monthly Rental, Starfish - NEW Monthly Rental 

June 2 6, 2021 Key West shows its Pride every day, and this is your chance to be a part of the celebration! The five-day schedule includes daytime pool and beach parties, late-night drag shows, on-the-water adventures ranging from snorkeling and kayaking to glass-bottom boat tours, a street fair, and pageants to select Mr., Miss and Ms. Key West Pride. Where To Stay: Butterfly Cottage - - NEW Nightly Rental, Poinciana Treetop - Nightly Rental, Bahama Getaway - Monthly Rental, Cayo Limón - Monthly Rental, Seas The Day! - Weekly Rental, Southern Skies - NEW Monthly Rental, Steamplant - Monthly Rentals

June 23-27 2021 Experience all things Mango through shopping, education and demonstrations. Stroll through Truman Waterfront Park to visit vendors, shop local shops, visit galleries, and order great food. Where To Stay: Solaris Pair-A-Dise - Nightly Rental

Enjoy a full 4 days of culinary events for every taste, including favorites from past years such as the Key Lime Cocktail Sip & Stroll and Key Lime Pie Hop and new favorites for Key Lime lovers like a Key Lime Scavenger Hunt and Key Lime University! Organizers have also added a few intimate culinary events for VIP Key Lime lovers! Key Lime Festival is July 1. Where To Stay: Casablanca - Nightly Rental, Chavez House - Nightly Rental, Chick-a-Pea Cottage - Nightly Rental, Poinciana Paradise - Group Rental, Potter's Cottage - Nightly Rental, Villa Luxe - Nightly Rental

Lobsterfest is August 12, 2021 Seafood lovers can chow down on Florida’s clawless lobster during a tasty “feast-ival” that features a savory schedule of events ranging from a traditional lobster boil to a lively street fair starring the sensational crustacean prepared in a variety of ways. The flavorful festivities celebrate the bounty of the Florida Keys lobster season that opens on August 6. Famous for its sweet and tender meat, the Keys’ spiny lobster often is served steamed with drawn butter, paired with a seasoned stuffing or cold in savory salads. Where To Stay: Casablanca Grande - Nightly Rental, Bohemian House - Monthly Rental, Copa Cabana - Monthly Rental     Book online or call one of our experienced local Vacation Planners who can help you choose the perfect vacation home for your nightly, weekly, monthly Key West rentals and extended stays with Historic Key West Vacation Rentals in Key West!