The Key West Songwriters Festival is the biggest gathering of its kind in the world each spring. For five days, the island becomes a stage where the writers behind today’s biggest songs share stories, collaborate, and perform in unforgettable settings throughout Key West.

Booking one of the Key West vacation rentals offered by 1800 Atlantic places you close to the music while offering the space and privacy to relax between sets. Enjoy Key West condo rentals with fully equipped kitchens and access to amenities such as an Olympic-sized heated pool, Jacuzzi, tennis courts, and 400 feet of private Atlantic Ocean frontage. 

For travelers who want to stay in the heart of the island, our Old Town Key West vacation rentals offer the charm of a residential neighborhood. The Toasted Coconut, a newly added Old Town studio tucked just steps from Duval Street, was built in the 1800s. For larger groups, Island Dreamin is a four-bedroom, 3.5-bathroom luxury retreat located between Old Town and the peaceful Meadows District, with a heated saltwater pool, waterfall feature, and outdoor kitchen.

Why the Key West Songwriters Festival Is Unlike Any Other

The Key West Songwriters Festival draws more than 150 to 200 songwriters each year, as far into the Florida Keys as you can travel and the southernmost tip of the continental US. Instead of distant stadium seating, audiences experience intimate performances where writers trade verses and share the stories behind the lyrics.

The festival blends country, Americana, folk, and multi-genre influences. Over the years, the festival has helped launch or elevate artists such as Florida Georgia Line, Jake Owen, Kacey Musgraves, Maren Morris, Michael Ray, and Randy Houser.

Experience Five Days of Music Across Key West

For five days, the island becomes a walkable stage. Performances unfold in historic theaters, waterfront amphitheaters, neighborhood bars, and open-air stages along Duval Street.

The Key West Songwriters Festival experiences often include:

• The festival showcases “in-the-round” performances, where three to four songwriters share the stage, taking turns to perform and explain the stories behind their songs.
• Ticketed performances taking place at seated and formal theaters like the historic San Carlos Institute and Key West Theater.
• Performances at some of the hottest Key West bars like Sloppy Joe’s.
• A large and FREE outdoor concert on Duval Street.
• Artists perform acoustic sets aboard catamarans with Fury Water Adventures.
• As a farewell to the festival, artists perform intimate acoustic rounds at popular Key West brunch spots.

Because events are spread across multiple venues, you can explore Key West between sets and discover new artists along the way.

The Key West Songwriters Festival Supports Meaningful Causes

Beyond the music, the Key West Songwriters Festival supports important charitable causes. Signed guitars are auctioned to benefit organizations such as the BMI Foundation, Michelle’s Foundation, and CreatiVets. There is also an online raffle to win one of the signed guitars, which also supports these great causes!

Find the Best Condos for Rent in Key West, Florida

Five days of music calls for more than a standard hotel room. Booking your stay with 1800 Atlantic gives you the space and amenities to enjoy the festival at your own pace. Our oceanfront Key West condo rentals offer all the comforts of home and more! Guests can enjoy fully equipped kitchens, private balconies, a washer and dryer, gated garage parking, and generous living areas. 

After a full day of performances, you can relax poolside, prepare dinner in your own kitchen, or unwind on your balcony before heading back out for an evening show!