We found Maui to be way more expensive than CR, but we stayed in the Wailea area which seemed pretty pricey.

Thanks everyone & nomad27. I did check out vrbo which is going to be helpful but since I am new to renting a condo, right now it seems confusing but I have to spend time & review that website. Ashton Kannapli Shores, Lahaina shores etc seem good.You are right condos in Kihei seem cheaper but I am not sure they have a view or are on a beach.I know I would prefer beachfront in a condo.I would try to avoid driving to the beach everytime we wanted to go.But lets see, once I review it further will know better.Thanks so much

I recommend looking into Costa Rica Villas for a great luxury trip with a small child. You’ll get the comforts of home without all of the work. A Residence club can offer you a safe home base on a beach with waves that aren’t too big for children. Places like Playa Flamingo are also very close to national parks and your son might really love to see all the howler monkeys and sloths hanging around!

I think you might be interested in checking out Belize. It would be closer for you than Maui and the beaches are great!

I would say without a doubt that Maui would be better for your child. I was there with mine when she was about the same age. The weather is more comfortable, the food is more familiar, and you can rent a condo (with kitchen, of course) at a reasonable price, which makes feeding a child much easier. (For example, look at the Kaanapali Ali'i.)

Unfortunately parts of CR are becoming Americanized. Our favorite little town recently put in a Burger King. :(