Guantanamo Bay (disputed between US/Cuba) used to be marked as US territory in Google Maps at least when viewed from the US, although interestingly, I'm looking at it now it doesn't say Cuba / United States along the border anymore.
I can't imagine the amount of crap they must go through on the backend to deal with these idiotic human politics. Humans suck.
Whatever Google depicts is what Google chooses to depict; and what they pick, at least in the U.S., is a function of what they believe people expect to see or need to see. They depict Taiwan as a separate state despite the U.S. government not recognizing them as such because it's what people expect to see. It's trivial to find maps in the U.S. depicting any alternative you desire. Equivocating popularity with government-mandated depictions is not constructive.
The dispute is about whether the lease agreement which allowed the US to use that territory as a naval base is still in force. Early after the Cuban Revolution, one of the US's regular rent cheques was mistakenly cashed, and the US claims this is recognition on the part of Cuba that the lease remains valid.
I agree. A better list of places to look in the maps are the current disputed areas between USA and Canada https://en.wikipedia.org/wiki/List_of_areas_disputed_by_Cana... In particular, what do you see in this map? https://www.google.com/maps/place/Machias+Seal+Island/@44.33...