This study develops a better understanding of the nature of urban parks from a safety perspective in two international contexts. To achieve this aim, the study is divided into two geographical scales (a macro scale and a micro scale) that test a set of quantitative and qualitative research methods. The macro-scale analysis provides an overall view of the effects of parks in the neighbourhood and at the city level. A particular focus is given to the impact of parks on housing prices. Overall, the findings show that parks function as an amenity that contributes to urban quality, which in turn influences property prices in Stockholm. However, this effect depends on a number of factors such as park type, location, and the level of safety and security of the parks. Safety also matters: Parks embedded in area with high-crime rates are less valued than in areas with low-crime rates. The micro-scale of study focuses on parks as a unit of analysis and looks at the environment of parks and how it triggers crime and affects people’s safety. The first analysis is based on whether—and, if so, how—park environments affect safety (crime occurrence) using the principles of crime prevention through environmental design (CPTED) as an inventory tool in a park in an area with a high-crime rate in Stockholm, Sweden. Building on the methodology from the first study, the second study investigates the nature of women-only parks (WOPs) in Karachi, Pakistan, by looking at both the environment of the parks and the users’ and non-users’ perceptions of safety. Regardless of context, the findings show that the safety conditions of a park are highly associated with the park’s environment (design and management features). Of importance to park safety are park size in relation to the number of access routes (entrance and exit points), the opportunities for surveillance in relation to the maintenance and the lighting conditions in parks. A clear lesson is that a CPTED-informed park design promotes guardianship and therefore should be encouraged, regardless of whether it is located in Stockholm or Karachi. However, the urban context does matter to park safety conditions and is highly dependent on the local, city-wide, and national contexts in which the park is embedded.