Our summer/beach weather usually arrives with reliablity at the very end of June and stays through into late September, early October.
That does not mean we don't have nice days (sometimes, a lot of nice days) at the beach in May and June, but you can't bank on it the way you can in July-September. And, it is also not unusual to have chilly days (mid-60's) on the sand during that time (despite the fact that it might be 85 degrees 10 miles inland, just like the Bay Area). We call it "the marine layer," and it is a thick bank of low clouds and fog that hangs around the coast (hence, "May Gray, June Gloom"). Being from San Francisco, you must be very familiar with this phenomenon. Your's lasts all summer, but ours is mostly focused in May and June.
It will pretty much be there every morning, and often burns off or pulls back over the ocean in the later morning/early afternoon - often revealing warm/sunny weather. But, it sometimes hangs around all day, so that it is coolish, breazy right on the sand. I'm sure there have been plenty of family beach vacations foiled by this weather. Many don't go to Southern California in June expecting to be wearing a sweatshirt during the day (I'm sure you see the same thing in Fisherman's Wharf all summer: out-of-place looking families from the midwest, huddled around each other in shorts/t-shirts on a downright cold, windy and cloudy afternoon in August).
As counter-intuitive as it is, October and March often have better beach weather around here than May and June. Go figure.
So, that being said, if July is an option, i would absolutly choose it over May or June. The later in July, the better. August is even better, if you can swing that.
Another factor is the ocean water temperature. People are often suprised how cold the water is here, relative to the East Coast. Things don't usualy warm up (which, for us, means mid/upper 60's, low 70's) until July. It is not unusual for the water to be in the upper 50's and low 60s well into June. That is pretty cold for most people. This means that a beach vacation in May will likely involve nothing more than a few quick and very chilly dips in the water. But, you Northern California folk are pretty hardy, so maybe you feel differently. I've seen families happily froliking in the water at Stinson Beach in 58 degree water, so who knows....
As far as rentals, yes, there are houses right on the sand for rent. But, most beach houses are rented out on a weekly basis (Saturday to Saturday). I'm not saying its not possible to rent one for a few days, but you may have to search around, and if you are going for a coveted beach-front house during the summer, I can see it being difficult trying to book for a few days.
Also try Newport Beach, which also has plenty of beach rentals on Balboa Island and the Balboa Peninsula -- although nothing on Balboa Island will be right on the ocean.
You could try vrbo.com, where people rent out their houses directly (not agent, serivice involved).
Laguna Beach Rentals, Laguna Beach Vacation Rentals by Owner on VRBO (http://www.vrbo.com/vacation-rentals/usa/california/orange-county/laguna-beach - broken link) It looks like people are renting by the night, but you may not find a beach-front place.
A less attractive option is airbnb.com
Vacation rentals, private rooms, sublets by the night - Accommodations on Airbnb. It is even less formal, and people will rent out their apartment or even a room in an apartment. But, it looks like they have some stuff in Laguna Beach.
There are, of course, many other legit vacation rental companys that have websites with lots of options. You can easily find them on google.
As far as price: there is a huge range. Most places quote by the week, and can go from $1000 a week to $25,000 a week. I would say most places are in the $2000-$3000 a week range.
Another option, although its a longshot, is to try for a cottage rental at Crystal Cove State Park. There, you can rent by the night, and be right on the sand for a modest price. Crystal Cove is a beautiful beach area tucked on the coast between Laguna Beach and Newport Beach. The only problem is that is it is very hard to get a spot. You can check them out here:
http://www.crystalcovebeachcottages.com/html/index.php. They are put up for reservation 6 months in advance (and sell out within seconds), so the summer months are all already booked. But, people routinely cancel, so its not unheard of to find a place. If you check reserveamerica.com often, you might luck upon a cancelation.
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