I would've thought a lot depends on where you are. Did an upgrade in the maldives to a villa on stilts along with a glass lounge floor. Worthwhile it for a couple of nights, but 7k for 10 nights would have been a waste.
Got a free upgrade to one on honeymoon in Jamaica,very nice laying on the sunbed with the pool lapping round but wouldnt personally pay for one,especially if,like us,you are all inclusive. Its a bit difficult for the waiters to get to you and a pain for you to get the bar as you are swimming across then trying to get your rum punchs back again We didnt use the swim up as much as we couldve done,very nice for a couple of days though.
The water bungalows like you get in the Maldives are magnificent. Got upgraded to one for our last four nights there and it turned an average holiday into a brilliant holiday - not so much because of being able to swim out from your room but because of the sea creatures casually swimming past. Not a wildlife enthusiast at all, but basking sharks, manta rays and various multicoloured fish were pretty impressive. Can't say I'd be that bothered by a private pool - would be nice, but not worth the several hundred quid that it will no doubt add to the cost of the holiday.
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Had a water bungalow in MAldives and it was brilliant. Totally unnecessary and very expensive but we also had an outdoor shower and jacuzzi.
Difficult without being arrested.