sounds to me like this is a problem regarding the inductive effect..remember, you wouldn't consider the size criteria because the the electron withdrawing group isn't part of the conjugate base..
so in another words, given that everything else is the same, the conjugate base would look like
halide-CH2-(C=O)-O(-) for each one.
so at this point you have to ask yourself, which would be the most electron withdrawing (or which is the most electronegative), and this is the fluorine. so since fluorine is the strongest electron withdrawing group, the base would be the most stable and the weakest (due to deactivation), hence making it the strongest acid.
hope this helps