April in Key West brings springtime adventures and The Songwriters Festival
Warm breezes, turquoise water and five days of unforgettable music.
The legendary Key West Songwriters Festival returns this spring — celebrating 30 years as the largest festival of its kind in the world. For five days and nights, music lovers gather in Key West for intimate performances and storytelling from the songwriters behind country music’s biggest hits.
Past festival performers have included stars like Kacey Musgraves, Florida Georgia Line, Jake Owen, Randy Houser and Maren Morris.
If you’ve ever dreamed of experiencing Key West during its most electric music week, April is your moment. And right now, several of our most beautiful homes are available during strategic dates.
Whether you’re planning a spring break getaway or a monthlong island escape, now is the moment to book.
April nightly rentals
- Chick-A-Pea Cottage (4BR/2.5BA/Sleeps 7): A classic Key West cottage with historic charm, a private pool, and tropical outdoor space — just steps from Duval Street.
- La Maisonnette (1BR/1.5BA/Sleeps 4): A stylish two-story condominium just one block from Duval Street with a shared cocktail pool and lush courtyard setting.
- Casablanca Too (1BR/1BA/Sleeps 2): A cozy Old Town hideaway perfect for couples looking to stay close to Key West’s restaurants, nightlife and cultural attractions.
- Potter’s Cottage (2BR/2BA/Sleeps 4): A charming historic cottage on Whitehead Street featuring a private cocktail pool and walkable access to Key West’s top attractions.
April monthly rentals
- The Pink House (2BR/3BA/Sleeps 5): A vibrant Key West retreat offering classic island charm and space to enjoy a full month of tropical living.
- Seas The Day (2BR/1BA/Sleeps 4): A comfortable monthly rental ideal for enjoying slow island mornings, beach days and sunset evenings.
- Fair Winds at the Foundry (2BR/2.5BA/Sleeps 6): A beautiful Truman Annex residence offering resort-style amenities and Old Town walkability.
- Copa Cabana (2BR/2BA/Sleeps 4): A historic Bahama Village cottage with a private cocktail pool, rocking-chair front porch and charming pool house.
- Azur Palm (2BR/2BA/Sleeps 4): A tranquil island waterfront home perfect for a longer stay and soaking in the rhythm of Key West life.
- My Happy Place (2BR/2BA/Sleeps 4): A welcoming monthly retreat designed for comfort, relaxation and easy island living.
Don’t miss the Songwriters Festival
Five days. Dozens of performances. Hundreds of unforgettable island moments.
Book your April stay now before these openings disappear.
Browse all homes here.
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