The large growth in the wind power industry in the past years. mainly focuses on a growing market and the development of large turbines and offshore farms. The high technical availability of wind turbines comes with a greater need for frequent maintenance. Current maintenance planning is not optimized, and it is possible to make maintenance more efficient. Condition monitoring systems (CMS) could resolve the growing wind power industry's need for better maintenance management and increased reliability. Such systems are commonly used in other industries. CMS could continuously monitor the performance of the wind turbine parts and could help determine specific maintenance timing. This paper presents a life cycle cost (LCC), analysis with strategies where CMS improved maintenance planning for a single wind turbine onshore and a wind farm offshore. Case studies are based on real data from Olsvenne2 at Nasudden (Gotland, Sweden) and Kentish Flats, in the U.K. The main conclusion is that CMS benefits maintenance management of wind power systems. Improvements can be especially shown for offshore wind farm maintenance planning.