You need to be sure to remove the scent entirely where he has peed on the floor by using bleach or ammonia. Otherwise, he will continue to pee where he had peed before. When I have a new puppy (8 weeks old or so) I leave them in a cardboard box with sleeping material in 1/2 and newspaper in the other 1/2 when unsupervised. The dog won't pee in it's bed and will pee on the paper. Then I take the newspaper outside. Next I remove the dog from the box when it first wakes up from a nap and take it immediately outside near the newspaper. The dog will smell the paper and pee outside. When the dog is inside you must watch vigilantly and grab the dog and rush it outside whenever it begins to squat before it pees on the floor. I have owned several dogs for their whole life span and have never taken longer than a week or so to housebreak a puppy. If you have let it get this old you have your work cut out for you. The main thing is to first remove all the scent of urine from your house or you are sunk. Then start from scratch using that method.