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The simple explanation is that weak intermolecular forces (the forces that make something condense to a liquid when things are cold enough) depend on the surface area (as well as many other things). But in the case of relatively similar non-polar isomers (where weak intermolecular forces are the dominant forces), the larger surface area will lead to the large force and hence the highest boilling point.
2,2 dimethyl propane is a compact, almost spherical molecule. Pentane is long and "floppier" so will experience more forces between molecules.
The underlying, but slightly simplified, explanation of this is that intermolecular forces (often called van der Waal's forces) depend on attractions caused by quantum fluctuations in the surface electrons of the molecule. These lead to short-lived dipole moments that can also induce dipoles in neighboring molecules to which the original dipole is attracted. The larger the surface area, the more opportunity for such dipoles to exist and therefore a stronger force.
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