I think he needs to learn to fall asleep in his own bed - getting the new bed was the perfect opportunity to do that... and I suppose after that first night he should have been given oodles of praise that he went to bed like a BIG BOY in his BIG BOY BED and the next night you probably should have stood firm that he do the same and he could earn such and such... (like a Cars movie in the morning?? - sorry!!) It's not too late! Also, I hope you aren't allowing him to watch TV / movie in the middle of the night... or he'll think it's okay that he can ask for this. My little one used to wake up and "want to go downstairs" (as if it's time to really 'wake up') and I had to insist that it wasn't time - pointed out the darkness and that nobody was awake. A few nights of crying about it happened, but she got over that one once she realized it didn't work and mommy / daddy didn't give in. I don't think the size of the bed will help or change his sleeping pattern. Try a stuffed animal or snuggly he can cuddle to help him fall asleep - maybe you can shop together for it so he can pick it out. You also probably need to give it some time because of the vacation throwing off his pattern a bit. Maybe for the next few days you have to run him more ragged than ever - spend lots of time outside - or by the beach / pond / lake - let him run around, bring him in the water, etc..... so he's too pooped to wake up wondering about the movie or where you are... or he might be able to settle much quicker if he's that tired, even after waking up briefly. I'd stand your ground about not letting him come into your bed to "fall asleep", and about not lying down with him in his bed either. Just walk in, tuck in, reassure, leave. Repeat? Once he sees that he's not getting anything other than reminded to go to sleep in his big boy bed all by himself (and possibly earn rewards?? - even a simple sticker chart?), he may give up the "fight". Good luck - I look forward to seeing other responses because we haven't moved my daughter to a toddler or twin bed yet... and I'm afraid that she'll also be getting up all night if we do!! She's always slept in her crib, and never in our bed - but I'm afraid the bed thing will make her think that she can get up whenever she wants to. Keep us posted!