It isn’t resonance. It’s an inductive effect, essentially.

Alkene carbons are sp2 hybridized and the electrons are held slightly closer to the nucleus. This has the effect of making sp2 hybridized carbons effectively more electronegative than sp3 hybridized carbons.

The effect is even stronger for alkynes (sp hybridized carbons) which have even higher effective electronegativity. For example the pka of propiolic acid is about 1.8.

In comparing H-I and H-F, when we lose a proton the charge will be directly on the atom (I- or F-). In that case it’s more stable on I(-) because as we go down a column of the periodic table the atoms get larger and can spread out their charge over a larger volume (polarizability).

In the case of the alcohol, the negative charge is actually on oxygen so polarizability is not a key difference here. The fluorine is electronegative and helps to reduce the amount of negative charge on oxygen through induction.