Looking to book a villa or cottage etc. for 6 people mid to end of Jan for 2 weeks. Which side of the island would you recommend. Is one side better weather wise that time of year and does one side offer more activities and attractions? Also any recommendations on accommodations from those who have been there done that?

I like Ocho Rios because you are somewhat central to other places. You are between Montego Bay and Port Antonio. I was there at a Villa named, "Frangipani" in September. We were able to get a driver and visit Montego Bay, Port Antonio, and Negril. Negril was the farthest. To get to Kingston from Ocho Rios is also doable for a day trip.

What is your total budget and what type of "activities/attractions" are you looking for? Negril has IMHO the best beach on the island, but I only know of a few villa-type properties on the beach, and most of them would not be very private. If you need a staffed villa, and don't care as much about the beach, check out TRYALL or ROUND HILL, but both of these require a car or driver. Anyway, if you post back, I'd be happy to make some suggestions.

luxurylink.com great deals on roundhill.com

Trident Villas more exotic over by port antonio

good personal experience there.

rockhousehotel.com negril best values

South side around kingston dodgy avoid like the plague.

www.bluecavecastle.com

fun if adventurous very unique good pricepoints in negril

over some old pirate Caves we explored...

Like being in a Pirates of the Caribbean movie...

I have travelled to Jamaica many times and most often stayed either in Montego Bay and/or Negril. However, in 2005 my wife and I along with another couple travelled throughout the island staying at a number of new places which opened our eyes to the areas normally unseen by most tourists/vacationers.

There a 2 particular places I would recommend for a different type of Jamaican holiday.

Treasure Beach on the west coast not far from Negril. It is a sleepy little enclave of 5 beaches. We stayed at the Calabash Inn and would not hesitate to return. Here is a link where you can get a lot of good information.

http://treasurebeach.net/guide/

The Silver Sand Resort is on the north coast halfway between Montego Bay and Ocho Rios. This is a wonderful place where to can take various excursion to a number of verying interesting places. Here is the link.

http://www.mysilversands.com/content/home.aspx

I second the Treasure Beach suggestion if you're looking for something a little more off the beaten path for Jamaica. My husband and I stayed in the then-newly opened Mar Blue Verandah, which was a perfect fit for us.

www.jamaicaescapes.com is a great villa website because it showcases villas in every price range and in each part of the island, except for Kingston. We've rented from them and been very, very pleased.

I've only been to Negril and love it, but have recently read good things about Treasure Beach (travel magazine article). I don't think Negril's really big on the villa-rental thing.