My wife and I went to Paradeisus Princessa in Varadero in late February. The resort was rated a 5-star, but the reality of Cuba is that these rating mean very little. The resort was fine, clean, well-kept (for the most part) and the staff very friendly.
Do not go to Cuba for the food . Although I was fairly content with the quality and selection, it does not compare with north american standards. Unfortunately, the resort tries to cater to various culinary tastes (i.e. sushi), but is never quite able to get it right. Strangely, they serve very little Cuban food, which I happen to like, so I was somewhat disappointed to not have found ANY fried plantains while we were there (maybe not in season, I don't know)
DO go to Havana if you can. It is a case study of dysfunctional central planning and its effect on a stately colonial city. If you can, try to spend a couple of days there (book one of the downtown hotels) and just hang out. You will gain a much greater appreciation for daily life that you will from the back of a tour bus. And, as amusing as it is, you won't have to listen to the propaganda from the tour leaders.
We were fortunate during our visit that we were able to meet up with friends of friends that are stationed with a foreign embassy in Havana and got a (priviledged) insider's look at their lives.
Trivia: the Cuban resort industry is 51% owned by an arm of the Cuban military. Once Soviet funding dried up in the 90s, they had to "diversify." So they went into the tourism business. Apparently, the top brass now oversee hotel and resort operations.
