Hi, Marie. Not to complicate things, but I took a look at the other threads you’ve posted for this trip. Maybe I’m missing something. There were lots of recommendations to avoid going from Toledo to the airport on your last day (and I totally agree), but I didn’t see anyone suggesting that you not go directly from the airport to Toledo on your arrival.
We have done exactly this for our last couple of trips to Spain and love it. I’ve used Suntransfers (Suntransfers.com) to schedule a private transfer, but I’ve always traveled with 5+ people, so a private transfer made sense, economically, in my case. For one or two people, public transport (train or taxi) might be better.
Toledo is a great place to settle in, unwind, and get over jet lag. It’s small, but not too small, and there is plenty to do for a night or two. It can get crowded on the “main drag” (Pl Zocodover to the Cathedral) during the day, but the rest of the city is pretty quiet, and the whole place empties out in the evenings once the day trippers leave (in a good way; it’s not deserted, with plenty of people still wandering and restaurants and bars open).
So, maybe a night or two in Toledo when you first arrive, then take a look at the train schedules for the rest of your trip and figure out the order of Sevilla, Granada, and a night or two in Cordoba, then end up in Madrid so you can easily catch your flight home.
Just another thought.
To your original question, if you didn’t want to overnight in both places and had to choose between the two, I’d pick staying in Toledo for this trip only because you have a lot of other nights in Andalucian cities, and you will get a similar “flavor” across all of them (although they are all different, with different vibes and subtleties). Toledo is different and would give you a different, more northern, Castilian, Spanish experience. Although I do agree with Carlos; I prefer the food in the south!
However, as another poster pointed out, if you are planning another trip to Spain, Toledo is very easy to get to from Madrid, so maybe Cordoba would make more sense logistically for this trip.
Regardless of what you choose, you will have a wonderful trip!