Got it - so you go out and do your hunting yourself. this looks fun. Just book good Airbnb.There are no Agencies period! nothing like that there. Just meet girls on the street or in Clubs. You may be able to bring a lady into a hotel but security may stop you but would probably take a tip to look the other way. Typically the hotel would want you to pay for the lady at full cost.
It is all situational, but generally you can spend time with a lady for between 5k - 10k pesos or 15-30 USD
I hope there are no safety issues in general. I have stayed in Varadero resorts before, but just went to Havana for a day.
Next time - I will stay in Havana and try to follow your advice to meet.