Windows 8 modern metro apps scale according to physical display DPI. PD8 provided correct DPI to Windows 8, but Windows 8.1 requires an update for that mechanism which is only implemented in PD9. You're running Windows 8.1, so the upgrade to PD9 changed how your Windows start screen scales itself. 5 rows of tiles is the norm, they only look large in comparison to undersized tiles when Windows assumes 75 DPI display (and you have 150 DPI at 1920x1080 on 15" screen).
I'd expect you get the tiles around the same *physical* size if you enable retina resolution for the VM. I'll have to get my hands on an rMBP to double check that.
UPD: At 1920x1080 in OS X and retina enabled for VM, start screen tiles are indeed a bit smaller. But this appears to be due to Windows scaling logic. The desktop fonts are tiny until you logout and login again, this is because Windows Explorer needs restart to pick up DPI changes.
Last edited: Sep 10, 2013