Historic Key West Annual Rentals

Many locals started on their journeys as casual vacationers, drawn by the island's vibrant culture, stunning sunsets, and relaxed atmosphere. What began as a brief escape often transformed into a lifelong adventure, with many choosing to settle in this tropical paradise after just a few days of exploring its charms.

At Historic Key West Annual Rentals, we are dedicated to helping you find the perfect home that caters to your lifestyle and preferences. We offer a diverse range of long-term rentals that are entirely furnished, ensuring a seamless transition for you. All you have to do is pack your bags and book your flight to Key West, ready to embrace your new life on this enchanting island. Whether you're looking for a quaint cottage in Old Town or a spacious home in the heart of the island, we have the ideal options to make your dream of living in Key West a reality.

Would you like to include your home in our portfolio? We offer management services for both furnished and unfurnished properties, enabling us to cater to a wider variety of homes. Our team will work tirelessly to keep your property in excellent condition, providing continuous maintenance and care to maintain its value.

We are dedicated to finding reliable and responsible tenants for your home. You can trust that your property will receive the utmost respect and care, providing peace of mind while we manage your investment.

Historic Key West Annual Rentals (305) 296 - 6996

  • Key West Chamber of Commerce Logo
  • Key West Business Guild Logo
  • The Vacation Rental Travel Guide - Most Outstanding Award for 2017
  • Florida VRMA Logo
  • VRMA Logo
  • AirBnB Super Host Badge
  • Vrbo Premier Host Badge