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The existence of a castle on Piel Island can be traced back to at least the reign of King Stephen (1135-1154) but after numerous attacks by Robert the Bruce none of this first castle survives.
The present structure dates originally from 1327 but was partially dismantled in 1403 by the Abbots of Furness Abbey (who owned it) so that Henry IV could not install revenue men in it. By c1429 it had been repaired, and on 15th June 1487 it witnessed its most dramatic claim to fame when Lambert Simnel landed on Piel with an army of Flemish and Irish troops to challenge Henry VII. Lambert Simnel claimed (falsely) to be the son of the Duke of Clarence, middle brother between Edward IV and Richard III. He had even been crowned as "Edward VI" the month before at Christ Church Cathedral in Dublin.
Henry Tudor had defeated Richard at the Battle of Bosworth Field to claim the crown in 1485 and now two years later fought Simnel's army at the ensuing Battle of Stoke Field near Newark on Trent supposedly the day after Simnel's landing on Piel; though how he could have got an army from Piel to Newark in a day I don't know - suggesting that the landing date is perhaps a little wrong.
Simnel's army was defeated by Henry in a hard-fought battle which resulted in higher casualties than Bosworth Field.
In an unusual and uncharacteristic display of clemency, Henry pardoned Simnel - acknowledging that he was a pawn of the Yorkists, in particular Richard Simon. Simnel even went on to work in the palace kitchens and finished his days as a falconer.
This brush with History was undoubtedly Piel's historical high point, and soon after this the castle fell into disrepair such that by 1530 it was described as having "long been in ruins".
For more information on the castle see:
EH Ancient Monument Listing Link
EH Grade I Listing Link
Wikipedia article Link
EH Visitor information Link
Note: To visit the castle, you will first have to travel over to Piel Island by ferry, see Link for information on this.

Piel Island is a little tear-drop shaped island of about 20ha (50 acres) which has officially a population of four. This makes it, probably, England's least-populated populated island. This entire population is probably accounted for by the family that lives at The Ship Inn. The owner of this inn being acclaimed the "King of Piel" - the present King (2013) being Steve Chattaway.
To get to the island a ferry runs from Roa Island (which is causewayed to the mainland) quite regularly during the summer months, but it is best to check whether it is running as it is affected by tide and weather.
Currently (2013) the contact information can be found on this website Link
The ancient castle on the island, once the property of the abbots of nearby Furness Abbey dates from the C14th ( EH listing Link ) having been licensed for construction in 1327. It was dismantled in 1403 but repaired in about 1429. It is an English Heritage site freely open to the public (provided you can get to the island) see visitor info. here Link
Wikipedia article on Piel Castle Link
The only other buildings on the island are a row of cottages; these do not seem to be inhabited (and the low population figures suggests they are not) but they seem to be in reasonable condition, and are perhaps used as holiday lets - but this is only speculation on my part.
There is a good Wikipedia article on the island here Link
Visit Cumbria article Link
Ship Inn Link