Oder, liebe natives?

Lizzie,

"Good for you!" würde ich übersetzen "Schön für Dich".

Hört sich dann aber irgendwie ironisch an, oder?

"Good for you" expresses unconditional support and encouragement for someone.
Is that what this means?

I'd try something like this:
Go ahead, go on vacation. No one will begrudge you it.

"Good for you" ist wirklich nicht das gleiche wie "Schoen fuer Dich"! Das Deutsche hat hier fuer mich immer einen negativen Nachklang; eine Mischung aus Neid und "interessiert mich doch nicht".
"Good for you" wird mehr im Sinne von "Mensch, das ist ja super, freut mich fuer Dich" benutzt, also ganz unvoreingenommen. Koennte hier also durchaus passen.

I take the point about it raising the question whether or not someone has earned it. I think that deserving is the most natural translation, but if it goes in the present tense, the connotations of having earned it (in the past) are not so great. You deserve it because everyone deserves a break, you deserve it because you are you, whatever.

To me, talking about begrudging already implies that you do really begrudge it - otherwise why use the word!

How about: You go on vacation, I won't hold you back.

or "I won't keep you from it."

wenn "good for you" mehr bedeutet "Mensch, das ist ja super,...", heißt das aber auch 200 %ige Unterstützung. Das wäre aber ein bisschen viel des Guten. :-) Dieses "Es sei Dir gegönnt!" soll aber in keinster Weise negativ gemeint sein!

Vielleicht also doch einfach "You deserve it". ??? Obwohl ich eigentlich ja nicht wirklich weiß ob er sich den Urlaub wirklich VERDIENT hat... :-)

I do think that anything to do with not begrudging, not holding back, etc. does imply a secret wish to do that very thing!

If it is simply about conveying to a colleague or someone that they should have a nice holiday, is it possible to get away from what is so hard to translate, since it is a completely German idiom anyway?

"Have a nice time!" is a very neutral way of acknowledging someone is going on holiday. You do not have to imply he has earned it or say anything of how you feel yourself about him going away or even care very much whether he really does have a nice time. (That is perhaps where English differs from German!)

I have always heard "es sei dir gegönnt" said with just a touch of irony, as if the person saying it had a say in the matter and had to grant permission for one to do something. Not negative, just a bit silly and regal if you will. I do not think "have fun" or "you deserve" it hits the mark at all. How about "Go ahead and go on vacation, you have my permission."

"Problem" gelöst!!!

HAVE A NICE TIME ist schön neutral und keiner weiß was man selbst denkt.
YOU'VE MY PERMISSION ist auch sehr gut zu gebrauchen.

Hängt aber immer davon ab zu wem man es wie sagt! :-)

Vielen Dank an Euch alle! Bin jetzt nicht mehr RATLOS !!! :-)))

Thanks!!!