Definitely. I've been going to a lot of private beaches in Malibu recently. Naples has been on my list for awhile now too.
There's usually some cheap used boards on Craigslist. Also, at the end of summer, most liveries are usually selling their old rentals on the cheap.
If you go to Naples you can go from the peninsula across the bay to the canal entrance. If it's a crowded beach day you could try parking on Naples plaza just off 2nd st and walk down Loreta walk to the canal and just jump off the side. Naples plaza always has parking because no one goes to the water from there. Check it out on a map and you can get to the bay or canal pretty easy and avoid the Mothers beach crowd