I agree that some time ago if you needed it, you had to bring it with you in checked or carry on luggage. Now a days, just about everything you want or need is available in Negril or close by. Brumahlia House in Sav has a great selection of power tools. If it is just a small job and the drill is not needed after, might I suggest renting one. I have a name and number of someone up in Red Ground that rents tools and construction equipment. One more option is to buy a used one here. On the way from the airport to Negril, stop in Sandy Bay. There is a guy there with a shipping container full of used tools, equipment, bicycles, fishing stuff, etc. It's like a yard sale and Canadian Tire clearance aisle all rolled into one. Have your driver stop at the Seaview Bar for the coldest Red Stripe between MBJ and Negril and then walk back a half block to the shipping container. One more option is these guys;

https://rtabiz.biz/shipping/

Just buy it on eBay or amazon and use their location in Miami as the shipping address. They will ship it to Jamaica and then email you the shipping and customs fee's. Once they are paid they ship it to Negril via the Knutsford Express. Surprisingly easy and actually fairly inexpensive.