I honestly would get him use to sleeping in a Kennel. Peanut has always slept in his- I have a larger one, and 2 old pillows in there for his bed and a big throw blanket, I also throw a blanket over it so it is like his little "den" He loves it! Sometimes he doesn't want to get out!
Get him use to sleeping in there and being alone, you never know one day you might need him in there