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There was already an arms bearing Bole family in Devon by 1401.  John Bole, armiger, is on record as a knight of Sir John Dinham of Wortham Manor, Devon.  In that year he received a grant of a one quarter share of several of Dinham's estates in Cornwall.  He was deceased by 1428 but he was likely the ancestor of the John Bole Sen. and Jr. of Enys near Saltash, Cornwall in 1450/51 who sold almost 300 acres of land at Saltash in 1463.  See John Bole of Devon and Cornwall

There are not many records from this period online but I next found a Roger Bole at St Stephens by Saltash in 1548. 

In 1613 a Roger Bole of Saltash, Cornwall (the Gateway to Cornwall, facing Plymouth across the River Tamar which forms the border between Cornwall and Devonshire) is the earliest Bowles to have a documented interest in Ireland.  In August 1613 he prepared his Will just prior to leaving his wife, Alice, and son, William, for a trip to Ireland where he already had interests.  He did not return as his Will received probate in the Diocese of Cork and Ross (which extends to both Cork and Kerry) in March 1614.  See Roger Boles of Saltash, Cornwall

The Boles of Huish