I think you need to be more specific regarding your requirements and maybe budget so that folks can be more specific with their recommendations. All the islands you have mentioned are very appealing in their own ways, and all have establishments geared towards kids. What else would be important to you? Aruba does not resemble any of the others too closely, except for maybe T&C for terrain.

Most of the hotels in T&C are condo style so very convinient with kids. We have a two year old and we stayed at the Sands recently and it worked out well. Many of the nicer resorts on Anguilla are hotels so no kitchen washer/drier etc. There are only two hotels on St John (Westin more kid friendly than Caneel Bay - again neither are condos). Most of the villas on St John are not on a beach so will involve getting the kids in a car to get to the nearest beach. Would like to mention that we recently returned from Virgin Gorda (BVI) and stayed at a nice villa on Mahoe bay which I thought was convinient also. It is difficult to get to so my first choice if you are going in the summer months would be T&C.

Just want to mention that the Westin in St. John also has wonderful condo./villa style accomodations with kitchenettes and some 3 bedroom units with a private pool. The access to the resort facilities including pool, spas and beach are very convenient as they have these golf cart type vehicles that ferry folks everywhere.

I'm leaning toward the westin at this point but I'm not too thrilled with the 700-1000 price range I got from them for Febuary. And it looks like all kinds of construction going on in T&C at the moment. I havent checked out Anguilla yet.

Westin St. John often comes up on priceline bids. People can get it for $150-300/night, compared to the high rack rates.

Look on biddingfortravel.com for a tutorial on priceline bidding if you're not familiar, or do a search on this forum as it has been discussed ad nauseum.

St. John has many, many villas and you might want to see if that may be a better option, especially since you have two young children. Many have pools which would be good for the kids.

St John's private villa stays are wonderful, but more geared to adults and older children IMHO. I specifically rented a villa for this July because it did NOT have a pool (I figured it'd be easier to relax without worrying that a 4 yr old got into it without adult supervision). That's me...but you (Ziggy) may feel that way that too with young kids.
I've stayed at WestinStJ and it's great for youngsters!! We'll be going back after the villa rental to give the young 'uns some activity/other kid cohort time.
Tuxedocat took the words out of my cyber mouth--there are wonderful hillside villas/condos there with easy access via frequently- running golf carts (or you just call and they'll be there) to take you to the main property. We always enjoyed the downhill walk, with iguana sightings, friendly greetings from hotel staff, and beautiful grounds.
The two bedroom Westin villa buildings have their own pools and BBQ pits (in addition to the big pool by the hotel); the three br ones , as T'cat said, have their own private patio individual shallow pools with "waterfall."
One idea to rent the villas there MUCH more cheaply than thru the Westin, in additon to the good ideas above for Priceline, is to look on a site like TUG or Redweek for timeshare/ "Vacation ownership" rental for a week. There cost far less than booking though Starwood/Westin.
Whatever you decide, have a great family trip!

So I took the neither option and opted for the Buccaneer in st. Croix. I undersand the beach there is not as great as the 3 islands I mentioned but I like what I see/read. Thanks for the input everyone. I dont have any resvs yet so its still subject to change.

When you are at the Buccaneer, my doctor has relocated to that resort and is running wellness clinics there. Dr. Kirana Kefalos is her name. Tell her her patient Janet says Hi and will be coming to visit one of these days.

Thanks but hopefully I will never meet her. Not in her office at least.

BTW, I changed my itinerary to 3 days in Secret Harbour in St thomas and 5 days at the Buc.

Have a great time. Secret Harbour has a very nice beach with some decent snorkeling. You could also take the little ones to Coral World at Coki Beach, and there is a tram/lift in St. Thomas that takes you to the top of a mountain for some terrific views. Little kids will love that too.