Although it doesn't exactly match your question requirements, in the early days of the Shuttle program Columbia had an instrument mounted on its tail known as the SILTS pod (Shuttle Infrared Leeside Temperature Sensing) which took infrared photos of the orbiter during reentry.
SILTS pod on Columbia (NASA)
STS-28 reentry SILTS image (NASA)
The infrared camera could rotate and look through one of two windows, one faced the backside of the orbiter's fuselage, and the other window faced the left wing. The left wing was chosen because it was already wired up with sensors from Columbia's earlier role as a test vehicle. The sensors in Columbia's wing could be correlated with the infrared images.
EDIT - after posting this answer I noticed that @ErinAnne mentioned SILTS in a comment to your question.
For your "possibly also relevant" question, there have been cases where the crew onboard ISS was able to photograph the reentry of departing Progress and Soyuz spacecraft.
One such situation was the reentry of Soyuz TMA-20M in 2016, the photo below was taken by NASA astronaut Kate Rubins from onboard ISS:
Soyuz TMA-20M reentry (NASA)
There was another similar mission where this occurred, I don't remember which one, and I remember a NASA astronaut saying that he was able to make out all three of the Soyuz modules (service module, descent module, orbital module) reentering separately. I remember he commented that it was pretty obvious looking at it which one you wanted to be in.