Unless of course you visit a gay guesthouse - even then I think it doesn't seem proper. I would rotinely flirt with the staff while staying at guesthouses at PSP/FLL however that's just it - friendly flirting.

It's not something I would do at lets say Claridges / Hotel De Paris you get the point.

However, there is such a thing as being too helpful...

Admit it - if he was cute and you were in the mood you might have gone for it!