Not the same thing at all, since the US never claims Cuba should be part of Florida.
http://en.wikipedia.org/wiki/Treaty_of_Paris_(1898)
and there actually was a war involved.
In a way, it does.
Consider: if Cuba were to become a capitalist country, how much of its land and other natural resources would be immediately purchased by US nationals?
Americans can take de-facto ownership of foreign countries without re-coloring any maps.