On our first couple of trips, we just added an international calling plan to our AT&T cell phone. Texts to/from home were cheap and calls within Jamaica were not too expensive. We only called our driver a couple times (we often pre-arranged pick-up times), and I think I called Rhodes Hall for a shuttle pick-up. In the end, we spent less than we would have if we bought a sim card and minutes from Digicel. The only caveat is to make sure that you turn-off the data function on your phone, as data is not included in the regular international plan and the charges are pretty hefty if you use it. Instead, you can just connect your smart phone to the wifi at most hotels and restaurants and get on the internet for free.

That said, if you find yourself travelling to Jamaica multiple times a year, it might be worth it to pick-up a cheap digicel or Lime phone, or at least unlock an old phone that you have lying around the house. I have an old blackberry that I might try out on our next trip.