Do you have an idea of which area in Cuba you're thinking of?
There are a few places where you can be right on the beach and then go right into town.
Varadero, Santa Lucia, Holguin are just a few places of many.
Personally, I feel it's better to stay at a resort right on the beach and be able to go into town that's about 15-30 minutes away, go sightseeing, dining, day trips, etc...you can be free to go back and forth easily.
Cayo Coco and Cayo Guillermo are a little more secluded and are about 45 minutes away from the main town...but it is still easily accessible and you can go for your daytrips as well...and are extremely beautiful...and from any resort, you can travel to Havana for a day or more.
I can give you some hotel recommendations but it would be easier to know first where you're thinking of going. There are many hotels in Cuba.
Here are some sites to give you an idea of what the different areas are like and where the resorts are located: http://www.cuba-pictures.com/hotels/inde... http://www.cuba-pictures.com/index.html http://www.cuba-junky.com/index.html
*Edit: never book a hotel that is less than a 4*, otherwise you'll be compromising quality in every aspect...
If you want to stay directly in Havana, try to book the 4.5* - 5* and the hotels that are overlooking the ocean.
If you want a Casa Particular, look at these links to help you decide by area and home.
Many enjoy staying at casas particulares as they are immersed with the locals and their way of living.
But again, if you choose to stay in a hotel right in Havana, make sure it is a good hotel that is reputable and high-star rating....the same goes for the all-inclusive deals...you have to make sure of the hotel/resort and its services, etc. An all-inclusive deal may be cheap because it's last minute or what not....but sometimes they're much cheaper because of the star-rating....I can't emphasize enough, don't go less than 4-4.5*.
Or you can simply stay in another resort area that is just outside of Havana and you can easily rent a car and drive out there all the time. Varadero is right beside Havana and not a long distance.
Whatever decision you make, it won't be wrong. Your trip will be exciting and adventurous. You will be made to feel very welcome wherever you go.
I wish you would have a chance to go to the Cayos...but either way, do try to enjoy the resort beaches if you can as well.