Anyone know how long (time) this drive is? Recommendations of where to stay in between to break up the trip?

The AA website puts this drive at 5hrs 17mins without stopping to see sights, get lost, have lunch etc. I find the times on the AA route planner are generally accurate but I am used to driving on Irish roads. As a tourist you might need to allow more time.

http://www.aaireland.ie/routes/default.asp

It would be a shame to drive from Kerry to Westport and not spend some time in Clare to see the Burren / Cliffs of Moher. I'd visit the Burren and the Cliffs on the way from Dingle and then spend the night in the Burren or Clarinbridge (or Galway city if you would like to see Galway - it's not much out of your way).

Thanks for the tip. We are actually meeting my family in Kinvara the following week and staying there for 6 days so we will visit all the sights in Clare during that time. We have heard so many great things about Connemara that we are figuring out if we can work in a trip up there.

If it's Connemara you want to visit (and I think it is a good idea) then you go right past it to get to Westport.

How about heading for some place like Oughterard and working out from there?

We just got back from Ireland and drove from Dingle and stayed in Doolin at the Harbor View B & B, near the Cliffs of Moher, then drove to Westport the next day through Cong, stayed in Westport, then drove through Connemara and stayed in Galway. We followed Rick Steve's recommendation for the route.