Annual. Windward Bay is a secret little gem on the north end of Longboat Key. This spacious property overlooks Sarasota Bay and the Sister Keys. Watch the sunrise in the morning and the manatees, dolphins and birds the remainder of the day from the glass and screened enclosed lanai. This 2 bedroom, 2 bath unit is clean, affordable and has a washer/dryer in the unit. Windward Bay offers two pools, fitness center, tennis courts, covered assigned parking and also outside storage. Residents have a deeded beach access across the street. There is also boat dockage available for a monthly fee at Windward Bay.