Calling mothers with older teens:

So my mom lives in NC because she had a job transfer while I live with my dad in IL. Every Christmas break and summer break I go down there and visit for 2 weeks in the summer and about a week and a half in the winter. I love going down there and it’s always fun because we usually go to the beach. Well I recently got back with my “high school sweetheart” we were dating for about 2 1/2 years and then we took a long break from each other (about a year). Well like I said we recently got back together and my mom absolutely adores him. She thought about paying for his ticket to come down with me over winter break. We are both seniors this year and we are 17 and will almost be 18 at the time that we would leave. The thing is I’m not sure if his parents or my dad would let him go with me considering we would have to share a room together while we’re there. How would you feel about this? Would you let your teen go?