Can’t-miss festivals and fun in the sun: Make your escape to Key West in April

Looking for a lively escape with an excuse for merrymaking this spring? How about blending a calendar full of reasons to celebrate with balmy breezes, turquoise waters, and a unique vibe?

Welcome to springtime in Key West! Allow the team at Historic Key West Vacation Rentals to show you around!

Here, your dreamy tropical escape is the reality of the season. Here we’re known for near-perfect weather — warm sunshine, gentle ocean breezes and cool evenings — ideal for beach days, sunset sails, and outdoor adventures. And, as luck would have it, as you’re unwinding and exploring far from the hustle and bustle of the mainland, spring is also festival season in Key West, when special events bring this laid-back little island’s creative energy to life.

 Whether you’re a foodie, a history buff, a music lover, or an outdoor enthusiast, there’s truly something for everyone in this tropical paradise. If you’re planning a spring getaway, here’s we offer your ultimate guide to the top events and activities happening in Key West.

Stay awhile, won’t you?

As winter fades and the island awakens with energy, April and May are packed with exciting events that capture Key West’s lively and laid-back spirit. Let Historic Key West Vacation Rentals put you in the heart of all the action, while offering the privacy and comfort of a home away from home, whether you’re passing through or settling into an extended stay. And whether you’re relaxing by the pool, exploring vibrant Duval Street, or snorkeling at Fort Zachary Taylor Beach, springtime in Key West promises an unforgettable experience. At Historic Key West Vacation Rentals, we offer luxury properties, boutique homes, cottages and condos, with stays ranging from nightly to monthly (and beyond).

Signature can’t-miss spring events

Locals know spring in Key West is synonymous with festivals, parades and cultural celebrations that attract visitors and capture the essence of the island’s unique spirit. Here are some standout events to add to your itinerary.

• Conch Republic Independence Celebration (April 18-27) — Think parades, mock sea battles and a drag race along iconic Duval Street. Every April, Key West pays tribute to its fun-loving, rebellious history with the Conch Republic Independence Celebration, a 10-day festival filled with quirky events like pirates battling it out on the high seas, a bed race through the streets and myriad lively parties and family-friendly activities, including, a 5K race, a street fair, a Hot Havana Night dinner dance and more. This beloved annual tradition commemorates Key West’s brief “secession” from the U.S. in 1982, embracing the island’s independent and free-spirited vibe. This April, join us in celebrating the 43rd anniversary of the island’s “Sovereign State of Mind.” Long live the Conch Republic!

• Mote Marine Laboratory’s Ocean Fest (April 12) — Underwater and outdoor enthusiasts, Eco travelers and families are encouraged to celebrate the marine environment at Mote Marine Laboratory’s annual Ocean Fest. Proceeds from this community celebration support the institution’s coral reef restoration and research programs. From 10 a.m.–3 p.m., at Truman Waterfront Park, guests will enjoy a day of crafts, games, music, food, local brews (for ages 21+) and shopping, as well as an opportunity to explore Mote Marine’s conservation and environmental exhibits. Meet scientists and other conservation and representatives from other environmental organizations from around Florida to learn about the important work they do and how you can help.

• Easter Artisan Market (April 20) — Pack up the family to enjoy the Easter Artisan Market, at Clarence H. Higgs Memorial Beach, where a free Easter egg hunt ensues from 10 a.m. to 2 p.m. Kids 12 and under can hunt eggs hidden around the park, and local vendors are onsite with food trucks, an outdoor market and arts and crafts booths. By way of entertainment, live music and tours of the Key West Wildlife Center are on tap. This event is hosted with the Florida Keys Healthy Start Coalition to improve the health and wellbeing of families.

• Key West Songwriters Festival (April 30-May 4) — Don’t miss this beloved annual tradition celebrating up-and-coming singer-songwriters at venues across Key West. Billed as the largest festival of its kind in the world, this 29th annual Songwriters Festival has historically been a career starter for top country talent. The festival has kicked off the careers of household names such as Kacey Musgraves, Florida Georgia Line, Jake Owen, Michael Ray, Randy Houser and Maren Morris. Join with other music lovers who flock to Key West for five days and nights of live music.

• Memorial Day Weekend Celebrations (May 24-26) — Here in Key West, you’re never far from a party. For Memorial Day, celebrate in style with myriad unique beach parties and patriotic tributes, including such diverse options as an air show, a dolphin rodeo and a sailfish tournament.

Be there this spring, when Key West is alive with annual festivals and holiday celebrations. We're looking forward to all these upcoming Key West events, and more. For updates on any event or for planning a fabulous holiday vacation, contact our local team! We're happy to assist you in finding your ideal vacation rental at Historic Key West Vacation Rentals and to provide the inside scoop on all things Key West.

Where to stay: The best in Key West

To fully experience spring in Key West, you’ll need to start with the perfect place to stay. Historic Key West Vacation Rentals offers a carefully curated collection of luxury vacation homes in prime Old Town locations, providing the ultimate in comfort, privacy and convenient access to all spring festivities.

Of course, your Historic Key West Vacation Rentals accommodation includes more space and privacy than you’d ever hope to find with a typical hotel vacation. We ensure you’ll find yourself close to all the action, including world-famous Duval Street and some of the most pristine beaches in the world. And with their flair for elevating your Key West vacation experience, our local Concierge Services team is ready to help you put it all together, including access to bike rentals, sunset cruises, private chefs and much more.

Plan Your Key West spring getaway today!

Springtime in Key West is waiting with non-stop excitement, sunshine, and unforgettable memories. From legendary festivals to epic outdoor adventures, it’s the best season to experience everything this island paradise has to offer.

Ready to book your stay? Peruse our website to find your ideal Key West vacation rental, and start planning your perfect spring escape today! To get you started, here’s a sample of some of our fabulous historic vacation rental properties:

• Azur Palm: If you’re looking for an intensely private beachfront experience, look no further than Azur Palm, a lush 2BR, 2BA home that entices from the moment you open the door. You’ll experience Key West’s legendary sunsets directly from your private balcony and fall asleep to the sounds of the sea from your king bedroom. Located near the White Street Pier, Higgs Memorial Beach Park and the Key West Nature Preserve, you’ll be centrally located. Duval Street’s restaurants and nightlife are a quick walk or bike ride away. 
• California Dreaming: Come stay awhile (a month or more!) and live like a Key West local in gorgeous California Dreaming. This 4BR, 3BA home accommodates seven guests in the lap of luxury. You’ll enjoy a chef’s kitchen outfitted with an Italian Bertazzoni range, a wet bar with filtered and carbonated water taps and lush tropical landscaping surrounding your saline private pool. Truly a dream home, this completely restored designer rental awaits you in stunning Key West.
• Dreaming on Duval: Can dreams really come true? They certainly do when you stay in Dreaming on Duval! Consider this 5BR, 4.5BA luxury property your base of operations during your Key West stay. Here, you’ll enjoy ample space, where your family or friend group can stretch out, including beside the private pool with an amazing waterfall feature. Sip cocktails in the shade, take a dip, and dine alfresco. Featured on HGTV’s “House Hunters,” this fabulous home is the ideal place to make your Key West dreams come true. 

See you this spring in Key West!

Perfect weather, thrilling events and endless island adventures make spring in Key West an experience like no other. Whether you’re indulging in fresh seafood, kayaking through mangroves, or celebrating the local music scene or the birth of the Conch Republic, there’s something magical waiting for you in Key West this spring.

Start by booking your ideal Key West vacation rental today! For more detailed information about upcoming events in Key West this spring, check out our events calendar, and consider planning your trip around these unforgettable experiences. See you this spring in Key West!

Published on Wednesday, April 9, 2025