Looking for a place to call home on Siesta Key? Our Siesta Key annual rentals provide long-term lease options for residents who want to enjoy year-round island living on one of Florida’s most beautiful barrier islands. Whether you are relocating to the Sarasota area, looking for a seasonal home for the winter months, or simply want to experience the Siesta Key lifestyle for an extended period, our annual rental listings offer a range of homes, condos, and apartments available for 12-month or longer lease terms.
Annual rentals on Siesta Key offer a very different experience from short-term vacation stays. As a long-term resident, you become part of the island community — getting to know your neighbors, discovering your favorite local breakfast spot, and watching the seasons change from the comfort of your own home. The slower pace of island life, combined with the convenience of being just minutes from downtown Sarasota’s shopping, dining, and cultural attractions, makes Siesta Key an increasingly popular choice for full-time residents and seasonal snowbirds alike.
Our annual rental inventory includes a variety of property types to suit different budgets and lifestyle preferences. Find beachfront condos with Gulf views for those who want to wake up to the sound of waves every morning, spacious single-family homes with private pools and yards for families with children or pets, and modern apartments in well-maintained complexes with resort-style amenities. Many annual rental properties on Siesta Key come furnished or partially furnished, making the move-in process simple and stress-free.
The Siesta Key and greater Sarasota area offers an exceptional quality of life with world-class beaches, a thriving arts and culture scene, excellent healthcare facilities, top-rated dining, and a warm, welcoming community. The area consistently ranks among the best places to live in Florida and the United States.
Browse our available annual rental listings below or explore our real estate opportunities if you are considering purchasing property on Siesta Key. For more information about long-term rental availability, contact our team or call 888-941-RENT. Also check out local attractions to learn what makes this area so special.