I still have that $100K USD party that I'm looking to throw somewhere in the Caribbean...
Not sure if you need suggestions, but Montserrat, where Sir George Martin's legendary Air Studios used to be is a beautiful, safe, remote, and very private island - with very decent rock 'n' roll history (look it up). I went there a couple of times last year and Sir George's house can be booked as a small hotel if you know who to ask. For more capacity, there are loads of villas to rent - all with pools, and it's possible to swing a pukka reception at the Governor's residence, if you know how (it's British Territory and the Foreign Office chaps there are bored and helpful). We hired Sir George's place for a project and used it as a recording studio, it's accessible by 6-seater prop-plane - or helicopter - from Antigua.
A live volcano makes it an interesting chopper ride in, but avoiding the hurricane season is advisable; it's right in the Cape Verde corridor. Let me know if you're interested. It's not wild Vegas-style nightlife you just make your own parties. I loved it.
Dude it's Bob you know the alcohol would be on point, the Caribbean would be a hell of a party. I suggest Atlantis that place is awesome.