Would you let your 13yo stay alone at the resort...

It's good that he's showing you signs of maturity before the trip by housesitting at home!
And you could just set the guidelines, leave contact numbers, give him the hours that you'll be out and say, this is us trusting you, we want to start treating you like a grownup, that sorta thing.
As long as you're confident that he'll stay in the room, I don't think there would be a problem.
 
I guess I side with the "trusting" Moms. My kids (now ages 17 and 13) take care of themselves at home after school until I come home from work. And 13 year old daughter is going to the Amazon in February with a school group. I have let them go on their own at Six Flags with walkie talkies to check in and we meet at pre-selected times to touch base. DD says I should point out that "she is not like a bad kid though". When we go to Disney this Oct I plan to spend most of the days with my parents while they ride the coasters. No problems with them so far.
 

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