High-resolution stereo and multi-view imagery are used for digital surface model (DSM) derivation over large areas for numerous applications in topography, cartography, geomorphology, and 3D surface modelling. Dense image matching is a key component in 3D reconstruction and mapping, although the 3D reconstruction process encounters difficulties for water surfaces, areas with no texture or with a repetitive pattern appearance in the images, and for very small objects. This study investigates the capabilities and limitations of space-borne very high resolution imagery, specifically Pléiades (0.70 m) and WorldView-3 (0.31 m) imagery, with respect to the automatic point cloud reconstruction of small isolated objects. For this purpose, single buildings, vehicles, and trees were analyzed. The main focus is to quantify their detectability in the photogrammetrically-derived DSMs by estimating their heights as a function of object type and size. The estimated height was investigated with respect to the following parameters: building length and width, vehicle length and width, and tree crown diameter. Manually measured object heights from the oriented images were used as a reference. We demonstrate that the DSM-based estimated height of a single object strongly depends on its size, and we quantify this effect. Starting from very small objects, which are not elevated against their surroundings, and ending with large objects, we obtained a gradual increase of the relative heights. For small vehicles, buildings, and trees (lengths <7 pixels, crown diameters <4 pixels), the Pléiades-derived DSM showed less than 20% or none of the actual object’s height. For large vehicles, buildings, and trees (lengths >14 pixels, crown diameters >7 pixels), the estimated heights were higher than 60% of the real values. In the case of the WorldView-3 derived DSM, the estimated height of small vehicles, buildings, and trees (lengths <16 pixels, crown diameters <8 pixels) was less than 50% of their actual height, whereas larger objects (lengths >33 pixels, crown diameters >16 pixels) were reconstructed at more than 90% in height.