Hi Sheena,
I am doing a one name study of the surnames Pennyfeather, Pennyfather and Pennefather with a website at www.pennyfather.org

In early records the surname can change between any of the above spellings. The meaning of the Pennyfather/Pennefather spelling is that of a 'miser', which can also be applied to the Pennyfeather spelling.

St.Kitts can be considered to be a stronghold now of the Pennyfeather spelling, although unfortunately to date I have little information of the family trees from that location.

Please let me know if I can be of further help to you

Best regards,
Trevor