All over Habana and Cuba in general are Casas Particular, where the residents rent out their extra rooms Air BNB style. This is where we stayed for $30/night. It was easy and our host had some good general information for getting around with. He had his friend come over and do breakfast for us for $5 each per day, this was also handy, because breakfast was hard to find and not great or cheap.
The level of communication will likely depend on how well you speak Spanish. English speaking Cubans are few and far between. A Spanish-English dictionary would be handy to have since you can’t just look it up on your phone.