I'm an owner of a legal (permitted) vacation rental house.  I started researching whether to go long-term rental or short-term transient rental over 30 years ago.  The bottom line is approximately the same.  While the transient rentals per day are much higher, one also has many more days of vacancy and much higher costs of maintenance, taxes, insurance, cleaners, property managers, etc.  Vacationers tend to not treat your house as they would their own homes.  The big benefit of transient rental however, is the owners' ability to use the house themselves when they choose.  You can't do that with a long term rental.  Most non-vacation rental owners don't understand this and merely look at the daily rental price and figure the owner is raking in the big bucks.  Well, the gross rents may be higher but so are the expenses.