I use outdoor rock speakers that are placed in a garden by our fence along the back end of our yard. The speakers run through low voltage wires (low voltage outdoor lighting) in pvc pipes underground to my house where the cable and sat. tv come through into my basement. I actually had a hole there already, because I used VoIP for a while before going back to AT&T, so had a nice fat hole for the speaker wire (as well as cat 5 for the video projector). A bit of silicone caulk over the hole seals it up nicely.
But the point is, holes can easily be drilled through the siding into the house, if need be. Just make sure to seal it up, as described above, and keep it inconspicuous (the holes in my siding for the cable, sat. tv, and now outdoor speakers, are situated pretty much directly behind my central air conditioner.