Search Nightly/Weekly Rentals
Search Monthly/Seasonal Rentals
The Key West Songwriters Festival is the largest festival of its kind in the world. The festival spans five days and nights where songwriters introduce crowds to the faces, voices and stories behind the songs! The festival takes place in Key West, Florida at the most popular beaches, boats, bars, resorts, and Historic Theaters the island […]
CELEBRATE ONE HUMAN FAMILY The Key West Pride event is one of the largest and most popular LGBTQ celebrations in the United States. Full of vibrant energy, spectacular events, and fun Key West activities, this is an event not to be missed whether you're a member of the LGBTQ community, a friend or simply looking to […]
Mango Fest Key West Celebrate the Annual Mango Fest Key West - Thursday, June 27 - Sunday, June 30, 2024 The only Mango Festival in Key West! Join us for this free celebration of everything Mango. See what the king of fruit offers at Mango Fest. Visitors enter a world of Mangoes. Experience all things Mango through shopping, […]
ANOTHER YEAR Welcome to the Key Lime Festival: America’s Favorite Citrus Celebration! In the Florida Keys we like to celebrate the things that make our islands unique. Citrus, eccentrics, people & pie. Our celebrations are fun, odd & unforgettable. Our people are too. Come on down to the birthplace of Key Lime Pie for a […]
Hemingway Days Hemingway Days is a long-standing festival celebrated annually in Key West, Florida, paying tribute to the life and works of Ernest Hemingway, the eminent author who once resided there. Commencing in 1981 under the initiative of local residents, including Michael Whalton, the festival has seen substantial growth both in size and reputation, attracting […]
Tropical Heat is the HOTTEST annual 5-day party for gay men ages 21 and up in Key West and the Florida Keys! The all-male themed parties, pool parties, clothing optional events, and adult-oriented entertainment promise to be HOT! August on our tropical island is always HOT, but during Tropical Heat it promises to be even […]
The Key West Lobsterfest began as an argument between friends over who made the best Lobster Chilau. Naturally the only way to answer this most important question was a cook-off! Contestants tweaked their age-old family recipes and judges were assembled. The inaugural contest occurred in the courtyard of the Rick's & Durty Harry's Entertainment Complex […]
Experience the ultimate girls' weekend at Key West Womenfest Key West Womenfest is an annual end-of-summer festival celebrating lesbians and attracting thousands of women from around the globe. September 4-8th, 2024 For decades, Key West’s Womenfest has attracted thousands of lesbians, bi-sexual, queer, transwomen, and allies to what is arguably the premier LGBTQ+ vacation destination […]
2024 DATES - 10/18/24 - 10/27/24 2024 Theme: It's a 90's Neon Cosmic Carnival! Fantasy Fest is an annual 10-day party in paradise for grown-ups. Started in 1979 by a small group of Key West locals, the party was created to bring visitors to the island in what was a typically quiet, but beautiful season. It […]
