Need suggestions for a first time family trip!

We are expecting to take a family trip somewhere tropical with my extended family in January. We’ve never done a trip of this scale, so we’re not sure how to go about selecting a destination. My mother in her late 60s, my two siblings, their significant others, my 21 year old niece, my wife, and my 2 year old. Quite a diverse range of ages and interests.

What we are looking for is an island beach side resort (ideally all inclusive for simplicity’s sake, but it’s not important), as my mother will only want to be sitting poolside/beachside for most of the trip. My wife and one of my siblings are not the type to sit and relax, they need to be able to go on excursions, or to town for shopping/ restaurants. We don’t really need special accommodations for the 2 year old, but being able to have a 1 bedroom suite (with a crib/pack and play) would be good, because if he can see us at night, it’s very difficult to get him to sleep.

Finally, our budget would be $500 or less per night. Just looking for some suggestions as a jumping off point, thanks!