High spatial resolution mapping of natural resources is much needed for monitoring and management of species, habitats and landscapes. Generally, detailed surveillance has been conducted as fieldwork, numerical analysis of satellite images or manual interpretation of aerial images, but methods of object-based image analysis (OBIA) and machine learning have recently produced promising examples of automated classifications of aerial imagery. The spatial application potential of such models is however still questionable since the transferability has rarely been evaluated.We investigated the potential of mosaic aerial orthophoto red, green and blue (RGB)/near infrared (NIR) imagery and digital elevation model (DEM) data for mapping very fine-scale vegetation structure in semi-natural terrestrial coastal areas in Denmark. The Random Forest (RF) algorithm, with a wide range of object-derived image and DEM variables, was applied for classification of vegetation structure types using two hierarchical levels of complexity. Models were constructed and validated by cross-validation using three scenarios: (1) training and validation data without spatial separation, (2) training and validation data spatially separated within sites, and (3) training and validation data spatially separated between different sites.Without spatial separation of training and validation data, high classification accuracies of coastal structures of 92.1% and 91.8% were achieved on coarse and fine thematic levels, respectively. When models were applied to spatially separated observations within sites classification accuracies dropped to 85.8% accuracy at the coarse thematic level, and 81.9% at the fine thematic level. When the models were applied to observations from other sites than those trained upon the ability to discriminate vegetation structures was low, with 69.0% and 54.2% accuracy at the coarse and fine thematic levels, respectively.Evaluating classification models with different degrees of spatial correlation between training and validation data was shown to give highly different prediction accuracies, thereby highlighting model transferability and application potential. Aerial image and DEM-based RF models had low transferability to new areas due to lack of representation of aerial image, landscape and vegetation variation in training data. They do, however, show promise at local scale for supporting conservation and management with vegetation mappings of high spatial and thematic detail based on low-cost image data.