Movies with three remakes (do musical remakes count?):
ANNA & THE KING OF SIAM, THE KING & I, ANNA & THE KING (Jodie Foster version), THE KING & I animated version
Unofficial remakes:
YOURS MINE & OURS, WITH SIX YOU GET EGGROLL, THE BRADY BUNCH MOVIE, the new version of YOURS MINE & OURS (or was that CHEAPER BY THE DOZEN?)
PILLOW TALK, LOVER COME BACK, SEND ME NO FLOWERS (sort of), DOWN WITH LOVE???