Consider The Meridian on Grand Cayman. It's a new condo complex on Seven Mile Beach. They have three bedroom condos, and they have elevators.

The only place in St. John I'd recommend with your restrictions is Caneel Bay, and even then, I'm not sure it will work with your budget. St. John is lovely but very hilly, and I think it would be challenging for visitors with mobility issues.

There are also the Hanalei Plantation Cottages on the North Shore of Kauai. One was used in the filming of The Descendants. They're pricey, and they book up: http://www.hanaleiland.com/hanalei_rentals/beach_cottages.html

I highly recommend a rental house in Caribbean/Bahamas, too. Suggestions of one of the "club" properties like Tryall or someplace like that in Jamaica is right on the money, but there are other islands that would have similar properties. Bermuda might work, too, but would be cold that time of year. Too many places to list that might work, but try Jamaica, Barbados, Anguilla, the US Virgins, BVI's, etc.

Another idea is to try Beaches in Jamaica or Turks and Caicos. I took my two kids to the Turks one a couple of years ago and it was terrific (I'm a single mom). Kids were happy, there were lots of activities for everyone, everything was included, we had a great huge suite. It worked well. Food was very good too. Service was excellent and friendly, and I remember seeing lots of multi-generational families, disabled access, etc. If you do that, get a cabana everyday so that your mom has a shady nice place by the pool and there is a "home base" during the day. Your two kids would be thrilled with the kids activities (they have great things for tweens on up, though mine were younger and loved kids camp). Easy to get to, too.

Wonderful idea!

Anonymous wrote:OP, you left out the cost factor.

This is OP, I did so intentionally because I want to know what's out there...but we are looking to keep it between $10-$15k all told.

OP, you left out the cost factor.