I haven't been on a whole holiday but I did once spend a day with the ex Mrs Gwylan in a nudist spa. It was pretty unerotic TBH - most people were middle-aged - Mrs G was probably the youngest person there - and there was certainly no danger of my, er, embarrassing myself.
It was a bit weird walking around with nothing on at first but I got used to it quickly and I liked swimming with nothing on - not something I'd recommend at the local pool though
There is a nice holiday camp in Negril, Jamaica, why don't you all go to there.
It's called Hedonism.
No need to worry if you get a stiffy as you can slide it in to whoever is in the vicinity and they really wont mind.
Failing that you can just sit it out and pump fist in the corner with no embarrassment (the waitress will even help you out)
With the added bonus of all that sun Red Stripe, reggae and rum cocktails its a win win situation.