Welcome!

Stay on Siesta, an affiliate of Beckmann Properties, is your premiere vacation rental company on Siesta Key and the surrounding Sarasota area. Whether you desire a cozy bungalow snuggled up to the sand or an elaborate beach home, Stay on Siesta will accommodate all of your rental needs. The quality, value, and variety of our homes are unequaled and we take great pride in making sure every aspect of your vacation, from reservation to departure, surpasses all of your expectations.

Known for our white sands and vast cultural attractions, Sarasota and Siesta Key have everything to offer. From the shopping and fine dining located on St. Armand’s and Siesta Key, to the bustling markets on Main Street and the fine art displayed all across town, there is a special reason why Sarasota has become one of the top cities in the nation to visit. Ranking #2 for the second year in a row, Siesta Key beach has once again topped the "Best Beach in the Nation" by the famous "Dr. Beach" himself, Mr. Stephen Leatherman. One step onto our fine, snow-white sand will confirm its ranking and will show you why locals and continuing vacationers call it #1. Once again, Sarasota has been included in AmericanStyle Magazine's annual Top 25 Small Cities for Art in America ranking in at an incredible #4. The cities uniqueness and commitment to the arts is just a couple of reasons we have consistently ranked in this annual competition.

With Stay on Siesta you can rest assured that your vacation will be as relaxing and carefree as possible. All of our rentals are professionally managed and maintained to the very highest levels. Our online reservation system is unrivalled in the industry, putting you one click away from easily reserving one of our Siesta Key vacation homes. Above all, our goal is to deliver a superior level of service and communication. Our mission is to create an unforgettable experience by offering "hotel-like" treatment to our guests, including concierge services, to help you better enjoy your vacation experience.

Josh Beckmann, President of Stay on Siesta and Beckmann Properties, has over twenty-five years of experience in Sarasota and Siesta Key real estate. With his extensive knowledge of the short term rental business, we can assure you that all your needs will be met by one of our experienced staff members. We are always available, 24 hours a day, 7 days a week, in order to make certain that your Stay on Siesta vacation experience is perfect. Once you get here and you realize that you don’t want to leave, Beckmann Properties can also assist you in purchasing a gorgeous home.

So come and stay in one of our Stay on Siesta vacation homes, enjoy our serene sunsets, swim and snorkel in our crystal blue waters, parasail, jet ski, kayak and frolic with our dolphins. Our wonderful homes and beautiful beaches await you...