I've used Island Rentals twice, and have the World Master Card that covered the CDW. Both were in low-season and it was under $US175/week for a Toyata Yaris - and they were both less than 1yr old cars in great condition. I just did a quick search and they are at $US200/week right now. So if mick is paying $US777 for 2 weeks for the same car, that shows you how much the insurance adds to the cost - and how much you can save if you are early enough in planning that you can order a World Master Card.
Also, I had the car delivered to Negril from MoBay after a few days, to time it so I had it for a 1-week rental. Doing that added $US30, but then I saved the $US20/person on the taxi drive back to MoBay airport at the end by returning the rental there.
I agree that if you are just staying in Negril, the route taxis, and even the regular taxis for late-night, are so cheap and easy, there is no need to rent a car. But if you do a few day-long trips like to YS Falls, Black River, Treasure Beach - those are easily over $US100 each - so a rental car makes definite sense for that. But I would never recommend it on your first trip to Jamaica (probably not just 2nd either) and you need to make sure you have the patience and mentality to drive there. Also get a good road map. Suggest you search the board for other people's experiences, both good and bad, before deciding - this is a common topic and there has been a lot posted on this topic.
