Measurement of plant characteristics is still the primary bottleneck in both plant breeding and crop management. Rapid and accurate acquisition of information about large plant populations is critical for monitoring plant health and dissecting the underlying genetic traits. In recent years, high-throughput phenotyping technology has benefitted immensely from both remote sensing and machine learning. Simultaneous use of multiple sensors (e.g., high-resolution RGB, multispectral, hyperspectral, chlorophyll fluorescence, and light detection and ranging (LiDAR)) allows a range of spatial and spectral resolutions depending on the trait in question. Meanwhile, computer vision and machine learning methodology have emerged as powerful tools for extracting useful biological information from image data. Together, these tools allow the evaluation of various morphological, structural, biophysical, and biochemical traits. In this review, we focus on the recent development of phenomics approaches in strawberry farming, particularly those utilizing remote sensing and machine learning, with an eye toward future prospects for strawberries in precision agriculture. The research discussed is broadly categorized according to strawberry traits related to (1) fruit/flower detection, fruit maturity, fruit quality, internal fruit attributes, fruit shape, and yield prediction; (2) leaf and canopy attributes; (3) water stress; and (4) pest and disease detection. Finally, we present a synthesis of the potential research opportunities and directions that could further promote the use of remote sensing and machine learning in strawberry farming.