Andalucia itinerary help

Go on, stay in Cordoba ...

3/18 Depart PDX.
3/19 Arrive in Madrid (3 nights).
3/22 Train to Toledo (2 nights).
3/24 Train or bus to Granada (3 nights).
3/27 Rent car and travel to Ronda (rent car on 3/26 because of Easter?) (2 nights).
3/29 Drive to Cordoba and drop off car (2 nights).
3/31 Train to Seville (3 nights).
4/3 Fly home from Seville.

Mar 20-27 is Semana Santa (Holy Week) in Spain. It is huge (and very special) in Seville. You may want to rearrange your itinerary to be there for part of that week. It will mean high season prices and lots of crowds, so you'd want to start looking at hotel reservations very early (maybe now?) and/or staying outside the center. Since you are flying home from Seville, you could stop there twice, once around the beginning of Semana Santa and then at the end of your trip.

You change the itinerary and go by train to Cordoba from Toledo, spend 1-2 nights. Cordoba will give you a small town experience with quite a bit to see and do, besides the Mezquita (which is a must-see). From Cordoba it's 2-3 hours to Granada by train/bus. They are currently working on the train tracks around Granada and may not be finished by next March. For now, the train goes as far as Antequera, then there's a connecting bus service to Granada, or take one bus all the way. Rent a car in Granada to drive to Ronda and return it in Seville. If you decide to go to Seville early, you could go by train from Toledo, then rent the car, drive to Ronda and Granada, return the car and end your trip in Cordoba. It's less than an hour by train to Seville, then a 15-minute taxi ride or a 30-minute bus ride to the airport.

A couple of thoughts about your stops -
Toledo - is likely to be colder and wetter than the towns farther south and lower elevation. I'd only spend 1 night or even see it as a day trip from Madrid. If you stay overnight, it adds at least an hour to your travel time to your next destination (by train), since you have to return to Madrid. The only train service to Toledo is from Madrid. Going from Toledo to Granada, you'd need the 8 a.m. train to Madrid to get the 9.30 train to Granada (that takes 4 hours with a transfer from train to bus).
Ronda - one day is sufficient to see the sights. It's less interesting and fewer sights than Toledo or Cordoba. At most I'd say one day driving there, exploring towns on the way, one day (2 nights max) in the city, and third day driving to next location. That's if you want to explore the pueblos blancos area. If you want to "stay a few days to really experience the town" do it in Toledo or Cordoba and Seville.

Thank you for the informative and persuasive replies. We have re-worked our itinerary so that we are able to be in Sevilla during Semana Santa. Although it isn't the most efficient travel plan, it is very do able. Here is our new itinerary...feel free to critique and offer your thoughts.
3/18 Depart Pdx.
3/19 Arrive in Sevilla and train directly to Cordoba (2 nights).
3/21 Rent car and drive to Ronda (3 nights). See surrounding area, including the Caminito del Rey
3/24 Drive to Sevilla and drop off car (4 nights)
3/28 Train or bus to Granada (3nights).
3/31 Train (or possibly fly) to Madrid (3 nights) Possible day trip to Toledo.
4/3 Fly home from Madrid.

As you have dropped your stay in Toledo I would advise you add a night to Madrid, at the expense of Ronda or Sevilla. Perhaps travel to Granada late Easter Sunday 27/4, then to Madrid 30/4.

Semana Santa is huge in Seville. Now's the time to book your hotel.

Chani, we are in the process of booking a lovely apartment in the center of Seville as I type. Plans are falling into place!

Jeanine - Maybe I'll see you there. I'm seriously thinking about it.

Chani, Please let us know if you will be in Sevilla. We will be able to see processions traveling down Calle Cuna from our balconies or the large roof top terrace on Calle Rivera. I am very excited! .