Stay away from the overtly family/kid friendly hotels. I wouldn't do the Wynn either. Their security can be a bit tight because of the Wynn name. On the strip, I've stayed at Cosmo, Caesars, and Planet with no issues. Most of the time they only have security watching the elevators during convention/event hours then just key elevator the rest of the time. Personally I'd never give a stranger a key to my room and leave them alone with it. I've never had a problem with meeting a girl somewhere like the bar or some other area away from the elevators and then walk with her back. I've never had to do anything more than flash the key and nod at the security person as we walk through.
Quite frankly, they know what's going on anyway. The entire security staff knows all the local girls and they can clock an escort a mile away. The key is just discretion so they have a reason to ignore it. Ask the girl to dress casually and bring an outfit to change into if that's your thing.
