Pack your flip-flops and dancing shoes! Book now for the KWSF

A rich musical heritage

Now in its 29th year, the Key West Songwriters Festival has helped launch the careers of artists such as Kacey Musgraves, Florida Georgia Line, Jake Owen, Randy Houser, Maren Morris and Michael Ray — proving that today’s intimate showcase can become tomorrow’s stadium tour.

Music is woven into the fabric of Key West. The island has long been a refuge for writers, artists and dreamers — including the late Jimmy Buffett, whose laid-back island sound was born right here. On these streets, storytelling matters. Lyrics matter. And during festival week, you’re never far from a songwriter sharing the story behind the next big hit.

Why stay in a private home?

Festival venues are scattered throughout Old Town and beyond, making a centrally located vacation rental the perfect home base. After a full evening of music hopping, you’ll appreciate:

• Private space to unwind
• Plenty of room for friends or family
• A full kitchen for late-night bites
• A pool or outdoor area to recharge before the next show

Festival dates fill quickly — and so do accommodations. If you’re planning to attend April 29–May 3, now is the time to secure your stay.

Homes currently available for festival week

• Potter’s Cottage (2BR, 2BA, 4 guests): Originally a charming artisan potter’s shop built in 1918, this private cottage in Old Town is ideal for couples or a small group. With comfortable indoor living space and a private pool, you can relax in between concerts, with easy access to festival venues.
• Southard Comfort (3BR, 2BA, 6 guests): Perfect for friends traveling together, guests will enjoy true indoor-outdoor living and poolside entertaining. Centrally located for music hopping, the spacious indoor layout is complemented by an inviting outdoor space.
• Chick-a-Pea Cottage (4BR, 2.5BA, 7 guests): This quaint island-style retreat is ideal for a festival getaway given its cozy and private atmosphere and walkability to all the island’s best sights. Enjoy open concept living/dining rooms and a private pool (with waterfall feature) to bring it all together.
• Chavez House (3BR, 2BA, 6 guests): Full of historic character and island charm, this quintessential eyebrow house in Old Town is perfect for small groups or family members to gather and spread out. Dade County pine and an updated kitchen with lanai access add to the home’s uniqueness.
• Casablanca Too (1BR, 1BA, 2 guests): This recently redesigned duplex offers stylish, comfortable accommodations that’s ideal for festival stays. Enjoy fresh air and sunshine from your front porch or backyard hot tub, along with convenient access to downtown venues.
• La Maisonnette (1BR, 1.5BA, 4 guests): This newly renovated two-story condominium is walkable to Duval Street and features a shared pool and beautiful outdoor area. Offering an intimate and inviting cottage setting with comfortable interiors, it’s the perfect place to unwind after all the festival action.
• Lilly’s Pad (3BR, 3.5BA,, 6 guests): A peaceful retreat, this bright and welcoming home with three ensuite bedrooms provides traveling companions with comfortable gathering spaces to rehash each show. Awarded the Florida Keys Preservation Star, it’s the perfect example of indoor-outdoor living at its best.

Don’t miss the music — or the perfect place to stay

The Key West Songwriters Festival isn’t just a concert series. It’s an intimate session at sunset. It’s hearing the backstory of a chart-topping song. It’s discovering your new favorite artist before the rest of the world does.

Book your Historic Key West Vacation Rentals home now and pack both flip-flops and dancing shoes. You’re going to need both!

Find more information about our homes, or discover the wonders of our concierge services on our website.