Mathematical modelling emphasizes the connection between mathematics and reality -- still, tasks are often exclusively introduced inside the classroom. The paper examines the potential of different task settings for mathematical modelling with real objects: outdoors at the real object itself, with photographs and with a 3D model representation. It is the aim of the study to analyze how far the mathematical modelling steps of students solving the tasks differ in comparison to the settings and representations. In a qualitative study, 19 lower secondary school students worked on tasks of all three settings in a Latin square design. Their working processes in the settings are compared with a special focus on the modelling steps Simplifying and Structuring, as well as Mathematizing. The analysis by means of activity diagrams and a qualitative content analysis shows that both steps are particularly relevant when students work with real objects -- independent from the three settings. Still, differences in the actual activities could be observed in the students' discussion on the appropriateness of a model and in dealing with inaccuracies at the real object. In addition, the process of data collection shows different procedures depending on the setting which presents each of them as an enrichment for the acquisition of modelling skills.