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Perched on the edge of the Gower plateau in Glamorganshire, as though anchored to its limestone bedrock, Weobley has a particularly attractive and memorable setting. The castle sits above the stark northern shore of the peninsula, just where the scarp gives way to Lanrhidian marsh and the sandy Loughor estuary.

The early history of the small lordship of Weobley is obscure, though it seems probable that it was among the first Norman holdings in Gower. The earliest reference occurs in a charter of liberties issued in 1306. Weobley was one of the twelve “ancient knights’s fees,” whose lords held a privileged position within the English community of the Marcher lordship of Gower as a whole. Most of these lay in the southern half of the peninsula, the area of primary Norman colonization, and it is likely that Weobley originally lay further south. Additional lands, including the site of the present castle, were probably acquired in the thirteenth century.

By this time, the fee was almost certainly held by the De la Bere family, although there is no direct proof until the end of the fourteenth century. A David De la Bere  appears in documents as steward to the De Braose Lord of Gower in 1292 and 1304. In the latter year he is known to have acquired "Leason", just to the east of the castle site by a grant which mentions both his wife and son, Peter. Moreover, his son, Adam De la Bere, witnessed a deed signed at Weobley itself, confirming the castle's existence by 1318. David De la Bere was still in Wales at this time - he is recorded as having been attacked by the men of Henry, Earl of Lancaster - and was therefore the most likely builder of Weobley Castle. He died sometime during the mid 1300s, but his two sons appear to have predeceased him and he favoured his nephew, John, as his heir.

Sir John De la Bere first appears in 1328 attesting a charter of John De Horton and seven years later he is seen to witness a charter of his brother-in-law, Gilbert Turberville of Coyty Castle. A document of 1397 records that Sir John  had died eight years earlier possessed of the castle. Its appurtenances were valued at ten marks per annum. His heir was an under-age boy, also named John. He may have been a grandson, possibly a younger son of the late Sir Richard of Crécy of fame whose own heir had inherited Kinnersley Castle through the right of his mother.

Sir John's eldest son, also John, was in line to inherit his mother's ancestral home of Coyty Castle. This finally happened upon the death of his cousin Sir Lawrence Berkerolles in 1411. He may not have taken up residence however, for there was much controversy over who should inherit, and his cousin Joan (Stackpole) and her husband Richard Vernon were living at the castle in 1412. They were under siege by another cousin and claimant, William Gamage. Joan's claims were initially upheld by the King, but William later won his property through the courts. This  John De la Bere died in his centenary year of 1414. Thomas, his son, apparently predeceased him. 

Meanwhile, John De la Bere  Junior of Weobley died in September 1403 at the age of only twenty-nine, probably in connection with the Welsh uprising sparked off by the Owain Glyndwr revolt. The lack of formidable defences at Weobley would have left it particularly vulnerable to the rebels. The revolt had weakened by 1406, but some four years later Weobley was described, with understandable exaggeration, as destroyed by the Welsh. John's baby son, Thomas, was now nine years old and he was placed in the care of his St. John cousins, latterly by Agnes Rodney, who made her will at Weobley in 1420. He came of age two years later, but apparently did not live long to enjoy his inheritance. In 1432, another John De la Bere (possibly a brother) is recorded as holding the castle, but he may have been the last De la Bere associated with it. He died the following year. Perhaps the remote and inhospitable Gower peninsula, and the increasingly dilapidation of the castle, led the family to move eastward and settle in their summer residence in Berkshire.