Pryor Lee Craigmiles was married on 27 Apr 1858 to his first wife Mary V. Grant (c1838-1864), daughter of Reverend John and Dolly (Winton) Grant of Roane County, TN. They had one son: Edgar Lee Craigmiles (b. 1859 in Roane County, TN; died circa 1930 in Escambia County, AL). Mary contracted consumption and was advised to move to a warmer climate. Pryor purchased a plantation in Thomas County, GA, and moved his family there. Mary died in 1864 while Pryor was fighting for the Confederacy. Edgar was five years old [at the time].

After the war, Pryor returned to Georgia. On February 12, 1867, he married Mary Francina Mardre Ponder in Thomas County, Georgia. She had previously been married to William A. Ponder, who seems to have died around 1865 (possibly in the Civil War). Pryor & Mary Francina had 8 children together.

See State Archives Of Florida:
http://dlis.dos.state.fl.us/barm/rediscovery/default.asp?IDCFile=/fsa/detailss.idc,SPECIFIC=2727,DATABASE=SERIES,

This collection includes the papers of the Craigmiles family of Tennessee, Georgia, and Florida. The papers contain a variety of materials documenting the family history.

Of particular interest is a letter from P. L. Craigmiles dated May 10, 1868, describing the condition of freedmen living on his Leon County plantation. Other records include a Georgia land grant; a list of items plundered from the P. L. Craigmiles household by Union soldiers in 1864; indentures; an 1862 receipt for items purchased by John Henderson Craigmiles as Assistant Confederate Commissary Agent; and an 1899 letter from P. L. Craigmiles that gives a history of the Craigmiles family. A recent typescript genealogy of the Craigmiles is also in the collection.