Holloway was born in Wells, Somerset, and entered the navy in 1760, aged about 13, aboard the 50-gun ship Antelope, under Captain James Webb, who sailed to Newfoundland to serve as Commodore-Governor of the colony.

Towards the end of the year, Commodore Hotham was sent to Barbados, to reinforce Rear-Admiral Samuel Barrington's squadron, with 5,000 troops for the capture of St. Lucia.

Some time after the conquest of the island, Holloway moved with Hotham into the Vengeance, but soon joined the Princess Royal, flagship of Admiral Sir Hyde Parker, who promoted him to commander.

[1] On 23 January 1780, he was promoted to post-captain, and returned to the Vengeance, to serve as Commodore Hotham's flag captain, and was present at the Battle of Martinique in April.

On the 13th the combined fleets of France and Spain set sail from Algeciras, and Howe ordered Holloway to take the storeships either to the Chafarinas Islands off Morocco, or to Oristano in Sardinia, should they be driven past Cape Tres Forcas, and to use his own judgement in bringing them back to the besieged fortress.

"Nauticus Junior", the anonymous author of Naval Atlantis, published in 1789, severely criticized Howe for selecting the Buffalo for this duty noting that she had been stationed as flagship in the Downs for some time as she was considered unfit for sea, and was seriously undermanned.

He was eventually appointed to the frigate Solebay in July 1786, and sailed for the Leeward Islands, where he served alongside Captain Horatio Nelson in Boreas, remaining there until September 1789.

[1] On 14 February 1799 Holloway was promoted to rear-admiral,[2] and shortly after was appointed assistant port admiral at Portsmouth, remaining there until the Treaty of Amiens brought a suspension of hostilities in late 1801.

In the course of the year, he made a survey of the nearby coast; and on his recommendation three 98-gun ships were stationed at Lymington, St. Helens, and at Southampton Water, to guard the Isle of Wight in the event of an invasion.

[5] In March 1809, the British parliament made permanent the island's courts of judicature, and re-annexed Labrador to Newfoundland, largely as a result of Holloway's lobbying.