You can look up most menu prices on the internet and hotel rates are public as well. I'm not sure what else you would really need to know. I've been on $2,000 vacations and $20,000 vacations and both can be had at the same destinations. You can look up private homes on vrbo.com or airbnb.com and save money vs a hotel but you'll miss out on many amenities and have to worry about taking care of every meal on your own. You can also try to find an all inclusive where you feel like your saving money but end up paying a premium for what is essentially cafeteria food and watered down well drinks.
I will say that the best balance of bargain and enjoyment was on Turks & Caicos. Stayed right on Grace Bay and walked to all restaurants. We ate five star cuisine and still only spent about $2,000 for a week. I have friends who stayed on Parrot Cay at T&C and spent $15k for essentially the same type of vacation, albeit with a much nicer room. It's also a quick 3hr flight from JFK for us tri-staters.
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