If you are talking southern California, I like Laguna Beach in Orange County and La Jolla in San Diego County. Laguna is very commutable, La Jolla is a stretch. SoCal real estate prices swing pretty dramatically, but they are always expensive. I'd wait for the next downturn (couple of years?) and buy the cheapest shack I could find in the most prime location I could afford. I think you won't lose in the long run if you can walk to the beach. Camp out in it until you can afford a remodel.