Your Family-Friendly Guide to Key West in 2026
Key West is full of experiences that make family vacations unforgettable. Staying at Parrot Key Hotel & Villas puts you near the island’s most memorable events and attractions, making it easy to plan a schedule packed with fun. From music festivals to local markets and petting zoos, there are activities that appeal to every age. Here’s a guide to some of the best things to do in 2026.
Jam Out at Mile 0 Fest
Truman Waterfront Amphitheater, Key West | January 27-31, 2026
Families can enjoy five days of Red Dirt and Americana music at Mile 0 Fest, set against the island’s sun-soaked outdoor venues.
- A Welcoming Vibe: The festival blends lively performances with a laid-back atmosphere, giving everyone space to dance, sing, or just relax on the grass.
- Plenty to Eat: Food vendors and local shops add to the experience, so you can enjoy snacks and shop for unique items between sets.
- Finding New Artists Together: Kids and adults alike can discover new artists, soak in the island vibes, and enjoy moments that bring the whole family together.
Get a Taste of Florida Keys Seafood Festival
Truman Waterfront Park, Key West | February 14-15, 2026
Seafood lovers will find plenty of activities to enjoy at the Florida Keys Seafood Festival. Attendees can experience it all, from trying fresh, local dishes and dancing along to live performances to discovering interactive activities for kids.
- An Air of Excitement: Celebrating its 20th year, the festival is alive with tradition and energy. Walking through the festival feels like stepping into a celebration of island culture, with the smell of fried fish baskets igniting your appetite, drinks flowing, and vibrant merchandise for sale.
- Family-Friendly Atmosphere: Families can sample a variety of dishes, enjoy performances, and take part in hands-on activities designed for younger visitors, like the Children’s Eco Discovery Zone.
- Opportunities to Learn: The festival also showcases Key West’s sustainable fishing practices, adding an educational element to the festival. Several of the conservatory organizations on-site offer access to marine life exhibits along with key info about how to enjoy seafood responsibly.
Enjoy Local Produce at Truman Waterfront Farmers Market
Truman Waterfront Market, Key West | Every Thursday
Shopping at the Truman Waterfront Farmers Market is a colorful, engaging outing for families, letting kids learn what’s in season while connecting with members of the local community.
- Something for Everyone: Fresh produce, ready-to-eat meals, and artisan goods line the stalls, giving visitors plenty to explore. Kids can enjoy tasting local snacks while adults browse crafts and meet local vendors.
- Idyllic Vistas: The market’s waterfront location provides scenic views, making a stroll between stalls relaxing and enjoyable. It’s a place to connect with the community, discover new foods, and pick up one-of-a-kind souvenirs.
See Ben Harrison Live in Concert
Key West Theater, Key West | January 8 & 21, February 5 & 17, March 5 & 25, 2026
Ben Harrison’s concerts at the Key West Theater bring humor, personality, and original music together in a small, intimate setting.
- A Peek Into Island Life: Audiences experience the island’s character through his witty anecdotes and songs inspired by local life. Older children and teens will enjoy the playful energy, while adults can appreciate the clever humor and rich storytelling.
- Enjoy a Unique Point of View: Each performance feels personal, drawing the audience into the experience. It’s an opportunity to enjoy music and entertainment that is quintessentially Key West.
Explore Animal Lovers’ Paradise at the Animal Farm
Stock Island, Key West | Second and Fourth Sundays of Each Month in 2026
Visiting the Monroe County Sheriff’s Animal Farm lets families meet a range of animals, from sloths and goats to birds and a capybara.
- A Great Place for Kids: The farm has a welcoming atmosphere that encourages hands-on interactions. Children can feed animals and learn about their care, making the experience both fun and educational.
- For Every Animal Lover: Parents can enjoy watching their kids connect with animals they don’t see every day. It’s a playful, memorable outing for animal enthusiasts of all ages.
Enjoy Local Art at The Art Walk
White Street, Key West | Third Thursday of Each Month in 2026
The White Third Thursday Art Walk brings families into the heart of Key West’s creative scene.
- A Range of Artistic Displays: Galleries, live demonstrations, and performance art make every turn interesting. Kids can explore visual and performance art while adults enjoy the works of painters, photographers, and jewelers.
- Look Up at Local Architecture: The event is also a chance to see the island’s architecture and street life, adding to the experience. Enjoy the views of homes behind iconic picket fences, showcasing beautiful, coastal-chic designs.
Walking through the Art Walk offers a mix of discovery, creativity, and community energy for everyone in the family.
Key West has something for every family, from music festivals and seafood celebrations to markets, art, and animal encounters. Staying at Parrot Key makes it easy to access these experiences while enjoying the beauty of the island. Whether your family loves live music, local flavors, or creative arts, Key West has plenty of options to create lasting memories. A visit here promises days full of fun, connection, and discovery for all ages.