The development of fatigue cracks at fastener holes due to stress concentration is a common problem in aircraft maintenance. This contribution investigates the use of high frequency guided waves for the non-contact monitoring of fatigue crack growth in tensile, aluminium specimens. High frequency guided ultrasonic waves have a good sensitivity for defect detection and can propagate along the structure, thus having the potential for the inspection of difficult to access parts by means of non-contact measurements. Experimentally the required guided wave modes are excited using standard wedge transducers and measured using a laser interferometer. The growth of fatigue cracks during cyclic loading was monitored optically and the resulting changes in the signal caused by crack growth are quantified. Full three-dimensional simulation of the scattering of the high frequency guided ultrasonic waves at the fastener hole and crack has been implemented using the Finite Difference (FD) method. The comparison of the results shows a good agreement of the measured and predicted scattered field of the guided wave at quarter-elliptical and through-thickness fatigue cracks. The measurements show a good sensitivity for the early detection of fatigue damage and for the monitoring of fatigue crack growth at a fastener hole. The sensitivity and repeatability are ascertained, and the robustness of the methodology for practical in-situ ultrasonic monitoring of fatigue crack growth is discussed.