Thank you all for your responses, they're so helpful and prompt. Red Stripes all around on me. :P
I get so anxious and excited like a little kid before Christmas when planning my next adventure to a new place. What's even more exciting this is the first time that I am going back to a West Indies country since I immigrated from Guyana 20 years ago. It's going to be nice bruckin' out some rantid Creolese (guyanese patois) widout de man dem tinkin' all me ah chat a "wah wah wu wah bah boo bah". It's really to bad that I didn't jumped onto this board earlier before going out and booking a place, definitely lots of wisdom here.
So my ultimate decision is to wing it. I'll stay at Roots for the first night and not lose my deposit. Wake up early the next day, scope out some of the spots and pick our final resting place. I figure this will be a good way to jump right in and see what all these places have to offer. Maybe some face to face bargaining might reward me with a more favorable rate, I've had some good success pulling this exact flex in Mexico.
Have any of you ever done something like this? I am going in the last week of February, will I run into a bunch of no vacancies if I don't book ahead of time?