The housing crisis in Ireland has rapidly grown in recent years. To make a more significant profit, many landlords are no longer renting out their houses under long-term tenancies but under short-term tenancies. The shift from long-term to short-term rentals has harmed the supply of private housing rentals. Regulating rentals in Rent Pressure Zones with the highest and rising rents is becoming a tricky issue. In this paper, we develop a breach identifier to check short-term rentals located in Rent Pressure Zones with potential breaches only using publicly available data from Airbnb (an online marketplace focused on short-term home-stays). First, we use a Residual Neural Network to filter out outdoor landscape photos that negatively impact identifying whether an owner has multiple rentals in a Rent Pressure Zone. Second, a Siamese Neural Network is used to compare the similarity of indoor photos to determine if multiple rental posts correspond to the same residence. Next, we use the Haversine algorithm to locate short-term rentals within a circle centered on the coordinate of a permit. Short-term rentals with a permit will not be restricted. Finally, we improve the occupancy estimation model combined with sentiment analysis, which may provide higher accuracy. Because Airbnb does not disclose accurate house coordinates and occupancy data, it is impossible to verify the accuracy of our breach identifier. The accuracy of the occupancy estimator cannot be verified either. It only provides an estimate within a reasonable range. Users should be skeptical of short-term rentals that are flagged as possible breaches.