When the natural villages in Jeju province are incorporated into the district of city planning, they are considered to be a small-scale residential districts. Therefore, a garden city should be planned that considers the characteristics of the villages to implement an appropriate street system, to use the area effectively, and to harmonize the villages with the surrounding communities. There have been an especially large number of problems with the street system in the city of Seogwipo, which was notified as the area of natural settlement. This study analyzes the problems inherent in street planning and the present condition of roads whose construction has been postponed for a long time due to several problems including an inappropriately planned street system. Based on the research of various documents, a practical street system has been investigated. Most of the residents in natural settlement units demand use of the continued the existing roads as well as the implementation of an effective street system. They ask for street planning under which the involved construction would take only a short period of time and would result in only minimal damage to their existing properties. Therefore, the street system should be planned so as to preserve the nature-friendly features of natural settlements, their surroundings and tourism resources. Even after streets hwve been planned and their completion you has been established, the plan should be continuously evaluated, analyzed and compared with other alternatives. The street plan should continuously incorporate improvement measures which would satisfy various aspects of the street system including land use, traffic demand, and future population demands. Both the amount of money to be invested and economical efficiency should be considered for street planning since the street system has a great impact on many industries. Unnecessary costs related to excessive road construction should be avoided. The street network plan should also include the complete evaluation of the natural topography as well as the surrounding. Considering these views, the data concerning the current condition of the city and the related investigation play an important role in establishing a street plan. However, the investigation of future construction plans by the city is as of yet at a very early stage. Therefore, there is an urgent need for the investigational study of the current city development plans. The street system for the natural settlement area should be established only after the thorough investigation of all aspects of street planning. In addition, the plan should be flexible enough to consider the characteristics of Jeju.