Hey Vega,
Just came back from Christmas in Tobago. The place was busy busy. We had a hard time getting accomodations - but then again it was a group of 12. I guess you're going around Carnival time so it might be just as busy.
Pigeon Point is good but crowded with tourists. There is a shop/school operating at the point. Nice place to kite but you'll need assistance to launch and land to clear the high wiindsurfer traffic. I didn't think it was that safe with all that crowd. The shop does a lot of rentals of the windsurfers. They didn't rent any kite gear but did give lessons. The winds were light when I was there 8-10 Knots but you had come early to get anything better. PP is a nice place but I wouldn't recommend it as it has a lot of tourist and cruise ship tour traffic.
Rockly Bay is much better - very very few people. It's about a 10 min drive from Store Bay - not walking distance. Pretty long beach area. The wind was a lot better too - side to side onshore at about 10-15K. Its next to the Tobago Plantations villa - they have a nicer beach, but lot of sunbathers and tourists.
The best thing is to get a rental car and get away from Crown Point and local tourist areas. Take a drive up the coast on the south side towards Scarborough and beyond.
There is a private beach not too far from Rockly Bay. Its called Canoe Bay, that was good. Not as long but the beach is wider and nicer. If you get there in the morning before the crowds come, better sessions. It's private, so be prepared for the topless european grandmas - why is it that the babes dont want to go topless?
Further up the coast, past Scarborough is a super nice beach at Hope - it think it was called Hillsborough Bay or Barbados Bay. Wide sandy beach, a couple of miles long and NO PEOPLE!!!! The wind was a lot stronger here aswell which is good for us! At its peak it was blowing about 20K, mostly onshore though.
There are a couple more up the south coast aswell - Princes Bay, Kings Bay that were nice aswell. If you drive - you will see some nice spots without any people. The key is to get away from the airport/resort areas where its usually crowded with tourists. Get a car, you'll get to the better spots and have the whole beach to yourself. Just heed the warning signs that none of the beaches are patrolled, so you're on your own if shit happens.
The East, North shore is very rocky and a bit dangerous for kiting. Great spots for scuba diving though. There are some beaches on the North West coast - but mostly small with rocky outcroppings and deep drop offs and strong currents. Only kite there if you're really good.
As for accomodations, I dont know what type you want - try
http://www.visittnt.com/ or
http://www.meppublishers.com/online/discover/. Has links to resorts, hotels, b&b, etc...
You might want to take a 16+M kite aswell incase the winds are low, wish I had. I had taken my 140 Spoiler and 12M Fuel in my NSI Deceiver bag - no problems on the airlines. Just don't fly BWIA - lot of people were delayed by days and lost luggage issues.
We were told to keep our wits about us about going into secluded places as crime is supposed to be high. We never encountered any problems and the locals we met were very friendly. Tobago is a lot more safer and laid back than Trinidad. Like travelling in any other country - you'll be fine as long as you exercise common sense.
Hope that helps. I don't know what the winds will be like in Feb as it is their summer. Hope its good for you.
Cheers and happy kiting.