Summer in Key West is synonymous with lively celebrations, thrilling activities, and experiences that highlight the island’s unique charm. With its tropical allure and laid-back atmosphere, the island transforms into a cultural and festive playground, showcasing its distinct heritage through memorable events. For travelers seeking premier accommodations, Bayfront Suites provides an unparalleled opportunity to relax in comfort amid these dynamic festivities.

Whether exploring our collection of Key West waterfront rentals or booking one of our well-appointed Key West luxury rentals, the summer offerings ensure each guest discovers a perfect blend of leisure and entertainment. Let’s dive into some of the key reasons summer in Key West is irresistible.

Key West Pride

Key West’s summer calendar begins with an inspiring and lively celebration of inclusivity through Key West Pride. Renowned for its ‘One Human Family’ philosophy, this event reflects the welcoming spirit that is embedded within the island’s community. The Pride celebrations embody creativity, harmony, and a shared sense of openness, all set against the island’s breathtaking tropical landscape. Throughout Key West Pride, visitors can discover dynamic events that showcase Key West’s joy and culture. The festival’s diverse programming, suitable for families and friends, highlights Key West’s commitment to creating an inclusive atmosphere. Visitors are encouraged to explore the array of parades, parties, workshops, and live performances that fill the island during this celebration. Pride is more than a Key West event—it is a reflection of the treasured values the community holds dear. From rainbow-colored decor to performances by legendary drag artists, the week transforms the island into a jubilant rainbow of activity. 

Key West Marlin Tournament

Fishing becomes an exhilarating pursuit during the Key West Marlin Tournament—an event seamlessly tied to the annual Hemingway Days celebration. Held on the storied “The Wall,” anglers test their skills by competing for captivating prizes while embracing the thrill of open waters. The tournament isn’t merely a sporting event; it’s a gathering for passionate participants and spectators who enjoy a seamless blend of camaraderie, skill, and island-style festivities.

Central to the Marlin Tournament’s appeal is the nightly celebrations that accompany the intense fishing action. Highlights include the highly anticipated Captain’s Dinner and a series of themed gatherings, all culminating in the winners’ awards banquet. While the competitive spirit is palpable, the social dimension of the event ensures everyone leaves with unforgettable memories.

Key West Marlin Tournament

Fishing becomes an exhilarating pursuit during the Key West Marlin Tournament—an event seamlessly tied to the annual Hemingway Days celebration. Held on the storied “The Wall,” anglers test their skills by competing for captivating prizes while embracing the thrill of open waters. The tournament isn’t merely a sporting event; it’s a gathering for passionate participants and spectators who enjoy a seamless blend of camaraderie, skill, and island-style festivities. Central to the Marlin Tournament’s appeal is the nightly celebrations that accompany the intense fishing action. Highlights include the highly anticipated Captain’s Dinner and a series of themed gatherings, all culminating in the winners’ awards banquet. While the competitive spirit is palpable, the social dimension of the event ensures everyone leaves with unforgettable memories.

Hemingway Days

Hemingway Days is an iconic celebration honoring the life and legacy of Ernest Hemingway, one of the island’s most famous residents. Key West blossoms into a vibrant cultural hub during this weeklong event, where visitors are immersed in writing competitions, historical tours, spirited contests, and culinary displays. Hemingway’s love for the sea, fishing, and storytelling unfolds through experiences that seamlessly intertwine literature with local island culture. From the enlightening Historic House tours to the boisterous Hemingway Look-Alike Contest at Sloppy Joe’s Bar, Hemingway Days offers engaging activities for visitors of all interests. The Lorian Hemingway Short Story Competition, a hallmark feature, continues to attract creativity and talent from aspiring writers worldwide. An absolute highlight is the Caribbean Street Fair, where revelers enjoy handcrafted art pieces, sumptuous local cuisine, and vivid displays of island talent. Meanwhile, the playful Running of the Bulls gives a wink to Spanish traditions, adding distinctively Key West flair. For a spirited close to the festivities, visitors are invited to visit the Papa Birthday Bash, complete with signature drinks and Hemingway-inspired storytelling at local watering holes. Combining dynamic literary homage with island charm, Hemingway Days remains an essential entry in the list of Key West things to do. 

Key Lime Festival

Few dishes are as synonymous with the Florida Keys as the iconic Key lime pie. The Key Lime Festival brings this beloved treat to center stage across five days of inspired celebrations. From interactive food tours to cocktail-centered excursions, the festival serves as an ode to the citrus fruit that has ingrained itself into the island’s identity. Visitors can enjoy classic favorites like the Key Lime Pie Hop or explore new additions featuring VIP tastings. Adventure meets indulgence as attendees pair culinary explorations with festival highlights, such as the Key Lime Cocktail Sip & Stroll. Beyond the pies and cocktails, the festival extends its focus to eccentric local traditions, harmonizing the citrus celebration with the vibrant personality of the Florida Keys. 

Key West Mermaid Festival

Brimming with wonder and imagination, the Key West Mermaid Festival celebrates oceanic beauty through folklore-inspired magic. Founded by a native, Kristi Ann, the festival achieves an exciting sense of whimsy through interactive events and community engagement. Highlights include Mermaid Meet & Greets, where attendees delight in learning about these mythical beings in a joyous, hands-on setting. The festival further embraces its aquatic roots with ocean awareness programming and themed activities such as Sailing with the Mermaids—a family-friendly sunset sail that lets visitors savor Key West’s golden evenings. Dancing by the seaside under starlit skies marks another highlight of the program, combining fun and significance as the festival extends a heartfelt message advocating for the protection of marine ecosystems. Bayfront Suites offers a convenient gateway to this fantastical celebration. 

Fourth of July

Independence Day in Key West transforms the island into a patriotic display of fireworks, music, and communal celebration. Visitors can explore historic Old Town, adorned with festive American decorations, or indulge in key lime treats while basking in the warm, sun-soaked air. July Fourth activities are lively yet family-friendly, ensuring an all-encompassing atmosphere suitable for visitors of all ages. The celebrations culminate in a dazzling fireworks spectacle, visible both from waterfront locations and aboard boats. For individuals seeking uninterrupted views of the vibrant display, staying in one of our Key West waterfront rentals proves invaluable, offering a picturesque vantage point to witness the magic unroll over the horizon. The Fourth of July festivities in Key West epitomize how the island seamlessly blends tradition with relaxation. 

Key West Luxury Rentals with Bayfront Suites

With so many Key West events lining the summer calendar, securing accommodations that enhance your stay is essential. Bayfront Suites provides a luxurious haven amidst the vibrant activities, allowing visitors to experience the island’s intrigue while enjoying premier service. Explore Key West luxury rentals for refinement tailored to your needs or browse our Key West waterfront rentals equipped with views of the pristine ocean. Whether planning family adventures or seeking relaxation after event-filled days, Bayfront Suites makes rentals in Key West as effortless as they are memorable. Combine the beauty of the festivals with comfort that speaks to your individuality, making your summer getaway the best it can be.