Spring in Key West: Why April Is the perfect month for a 30-day island escape

The magic of a month-long stay

How would you like to unpack for a month? Physically and emotionally! An extended stay gives guests something a typical vacation can’t — the ability to live, not just visit, the famed Conch Republic. Remote workers enjoy breezy mornings on shaded porches, families appreciate room to spread out, and long-stay guests discover the lesser-known corners of Old Town — from neighborhood bakeries to pocket parks to quiet morning walks under flowering royal poincianas.

Our concierge team helps guests connect to the island’s vibrant culture with curated recommendations, private tours and reservations that showcase Key West’s food scene, marine experiences,and storied history.

Live like an island local

• My Happy Place: This aptly named 2BR, 2BA shotgun-style home will change anyone’s attitude — perfect for a full month in the sun! From its delightful mosaic-tiled, covered front porch to its backyard dip pool, this home is loaded with comfort and charm. Being in the heart of Old Town makes this a fabulous choice for access to all that Key West has to offer — including restaurants, groceries, shops, galleries and Mallory Square.
• Three Arches in Paradise: For guests seeking the character of Old Town combined with the convenience of modern comfort, Three Arches in Paradise delivers both. This 3BR, 3.5BA monthly rental offers open living spaces, and a dreamy private pool surrounded by lush greenery. The home’s architectural charm — including its namesake arches — creates an unforgettable sense of place. Its central Old Town location makes it easy to bike everywhere: beaches, dining, galleries and sunset celebrations.
• Copa Cabana: Originally the home of a Key West cigar maker, this conveniently located cottage with cocktail pool will delight you. Your guest (or older teen) will enjoy their own space in the pool house with kitchenette, half bath and sleeper sofa. 

April brings culture, color & celebration

Some of the island’s most unique annual events happen in springtime, perfect for extended-stay guests who want to immerse themselves in Key West culture:

• Conch Republic Independence Celebration: Parades, parties, the famous Great Sea Battle, and tongue-in-cheek “secession” festivities. The 44th annual  celebrates the Conch spirit and takes place next year from April 17-26.
• Viking Yachts Key West Challenge: A buzzing boating weekend uniting Viking Yachts owners, anglers, and families for five days of competition, celebration, and community. Multiple events and gatherings take place from April 8-12, at Dante's Tiki Bar, 700 Front St.
• 30th annual Key West Songwriters Festival: This spirited festival takes over the island from April 29–May 3, uniting more than 200 renowned and rising songwriters for over 60 unforgettable shows. Recognized as the largest festival of its kind worldwide, this milestone celebration transforms Key West into a stage for the stories behind the hits.

Whether you join the festivities or watch from the sidewalk with a cold drink in hand, April’s celebrations offer a playful, uniquely Key West experience.

Your month in paradise starts here

Historic Key West Vacation Rentals offers a curated collection of historic homes, exceptional concierge services, and local insight you won’t find anywhere else. Let us help you plan your perfect April retreat — a month of renewal, discovery and authentic island living. Start planning your next adventure here.