Have you considered Antigua, Grenada, Barbados, St. Barts or St. Lucia?
I can second all of the above as I have fond memoies of each of these countries.
I add Turks and Roatan, Hondurus.
Caveat: i haven't made it yet to t&c, mostly because years ago when maid service, etc was common, the resort host tacked on $250usd for departure cleaning (way before airbnb normalized this). And, as I always had weekly cleaning incl in my rentals 7yrs ago, this rubbed me the wrong way. No cleaning and a $250 fee...nah, im not doing linens laundry AND paying $350 cad.
Be sure to ask the right questions if you are booking privately.
