Between sorrento, Pompei, positano and Ischea which location would you
recommend to be the most convenient for us to do some sight seeing ,
indulge in food & the beaches?
Ischia would be good for beaches but not as a base for exploring the region: it's too far away.
Positano has a beach but is accessible only by ferry (which can't dock if the sea is too rough) and bus, and has steep hills/ lots of stairs to deal with. There also is very little to do there when the weather doesn't cooperate. It wouldn't personally be my choice for a group of 14. Pompeii the town is really only good for seeing Pompeii the excavation.
So my choice would be Sorrento. There is ferry, bus AND commuter train service from there, and it's big enough to offer a wide range of restaurants and other tourist amenities. Pompeii (the excavation) is very easy from there by (very cheap) commuter train as would be a day in Naples, if hitting a rainy stretch.
Whether you can find a villa there that would accommodate 14, I don't have an answer for. The clock is definitely ticking for nailing something down somewhere ASAP, though, as bookings started to fill for high season months ago.
2nd week of August for 5 nights (tue-sun)
You will probably burn a good chunk of the first day traveling to the region (where are you coming from?). Where are you headed to after your stay? Be advised that the A.C. or Sorrentine Coast are not places you want to be the night before a morning flight out of Rome or even Naples, if that flight is early, If that is the case, you'll want to spend the night closer to your airport of departure.
Capri island & blue grotto tours...
If there's a tourist attraction borderng on a "trap" on Capri, it's the Blue Grotto. It's a real time-and-money suck for the very few minutes the boats spend in the thing...when they can even GET in the thing. Just my IMHO but the little town centers and stuff like the grotto are going to be HEAVING with day-trippers in August, and the ferries there and back are quite expensive*. I'd spend some time reading up on this trip to make sure it's something your entire group would enjoy? We've spent time on the island but also stayed there versus day-tripping it from Sorrento or the A.C.
*You might do better finding a company that will organize a private tour for a group as large as yours.
Is it convenient to hire a car?*
I'll vote with wbfey1 and say definitely not, not during high season. The roads will be very, very congested and just finding parking would be a challenge at best. Then there's avoiding the ZTLs in Sorrento (should you base there) and just trying to maneuver a large van around. Even finding a rental large enough to hold 14 + luggage would likely be a challenge. Hiring a service just to get all of you TO your rental from, say, a major train station and then back to that station might be a possibility. Any way you shake it, moving 14 people to/from and/or around the region is going to involve some cost and and be somewhat time consuming. Other than getting there and to your next location, not trying to do EVERYTHING together is advised, especially with a number of small children in tow. IMHO, a car is not the answer.
Oh, and Vico Equense isn't serviced by ferry so you'd be using train or buses to the A.C. from there and to Sorrento as well for ferries to Capri.