1.

Huey Lewis & The News - If This Is It

Start off at the beach with this great song and amazing video starring Huey Lewis & The News.
2.

Bananarama - Cruel Summer

The definitive 80s summer song. (Plus tons of bonus points for inclusion in The Karate Kid.)

3.

David Lee Roth - California Girls

Diamond Dave at his finest.
4.

Bryan Adams - Summer of '69

5.

Kenny Loggins - Playing with the Boys

Easily the most ridiculous video even for this list. "Playing with the Boys" was just one of Kenny Loggins' contributions to the Top Gun soundtrack and can be heard during the infamous volleyball scene.