re: Negotiating vacation rental fees

I have a friend who makes travel plans to a destination but doesn’t book lodging until less than 2 weeks before he leaves. He finds available properties on VRBO or Airbnb, contacts the owner/manager and makes a much lower offer than the advertised rate. He says he gets rejected a lot but always finds something for half price or better. I don’t feel comfortable traveling like that but he makes it work. Many owners would rather collect something over their own costs rather than their property generate nothing.