If I was the person in charge of enforcing it, I would probably do something like:
1 - Make it illegal for Airbnb style services to operate in that area, including making a website available, advertising the service, taking listings in that region, etc
2 - Threaten to jail or heavily fine senior employees if law broken
3 - Offer a legal route which involves an audit trail of bookings being supplied to the local gov
4 - Use audit trail to deal with rule-breaking landlords
Steps 1 and 2 are essentially how the US government deals with foreign gambling websites.