Wants: Best weather possibilities w/ 4 or 5 star type, (on a nice beach w/ child friendly pool) accommodations with 2/3 bedrooms and full kitchen—Good dining options, and at least fair to good shopping. I’ll be travelling with wife, 2 year old daughter and mother in her early 70’s. Getting a good deal is always important and my hope is to stay under $1,000 per night if possible. Departure city is Columbus, Ohio if that matters. Some destinations offer poor flight schedules…especially when travelling with a toddler.
Over the years I have been to several islands, but obviously my experiences are limited based on the numerous options. I really could use some help making an informed decision.
The Grand Caymans will be my “old reliable” option but would prefer to try a new destination. I have not been to Aruba, Barbados or Anguilla just to name three islands of interest. I certainly am open to ANY suggestions.

First off, no one can guarantee you good weather but generally speaking December weather throughout the Caribbean is some of the best of the year so I wouldn't worry too much about that.

Anguilla is a wonderfull island if you are seeking great beaches (there are 35 of them around the island) and fantastic restaurants (you'll have a choice of about 80) but you won't find very much shopping (other than a few "trinket shops), it's a rather expensive island and you may find it a little difficult to get to from Columbus. Check out KU or Shaol Bay Villas as they should be in your price range.

Barbados has all you are seeking but I've only stayed at Sandy Lane which may be outside your budget. There are, however, lots of other accomodations on the island in your price range.

Aruba is very "Americanized" and topigraphically is similar to both Grand Cayman and Anguilla. It has everything you are seeking and probably is the easiest island on your list for you to reach from Columbus. The island is also the most "crowded" of the places on your list.

Hope this helps.

if you like gc you might like provo in turks & caicos. the terrain is similiar, good diving/snorkeling. provo has excellent restaurants. grace bay beach is 11 miles of blindingly white soft soft sand next to gorgeous calm (protected by reef) tourquoise water. you can get usair flt#s down 2592 & 1059 in 5 1/4 hrs. ret #s 1060 & 3186 in 6 1/2 hrs for $661 per person. there are several suitable resorts for your family. i'd like to recommend the somerset. if you stay in the stirling house section (all beachview) 2br is $1100 3br is $1350. the garden view rooms are less. http://thesomerset.com/
numerous options if somerset is too pricey. http://www.wherewhenhow.com/turks-ca...otels-resorts/

provo has limited shopping options

I know the weather can be unpredictable. I was thinking that the weather in early December might be too cool or at least cooler in the northern part of the Caribbean.

Some of the places we've looked at are: The Landings, St Lucia, Smugglers Cove, Barbados and Meads Bay, Anguilla. We've always enjoyed the condo-type setting. It just seems to work better for our needs.

The mention of The Somerset is a great suggestion. We looked at that spot when we visited the Turks nearly a year ago. We really enjoyed the beach but are hoping to visit another island this December.