The former One Direction star, 27, was performing in San Diego on Monday night as part of the US leg of his Love On Tour, to a crowd of over 16,000 people.
Among the audience, his mother, Anne, girlfriend Olivia, and her two children with former partner Jason Sudeikis, Otis, seven, and Daisy, five, were spotted in clips uploaded to social media.
In one adorable moment, it appeared Anne was dancing with the children, as they all looked to have a whale of a time.
One concert-goer captured a video of the Watermelon Sugar singer’s mum frolicking with one of the kids as Harry performed One Direction’s hit What Makes You Beautiful.
The fan posted the sweet moment to Twitter, captioning it simply: ‘anne <33’.
The children could be seen wearing protective earmuffs and carrying a teddy bear, with the fan writing they ‘had the time of his life’ at the show.
In another clip uploaded by a fan, Olivia was seen bouncing around the floor with the little ones, before they run around in excited circles as Olivia applauded.
Olivia, 37, has attended a number of Harry’s concerts in recent weeks, and was recently spotted making shapes on the dance floor during his North Carolina show.
As Harry got stuck into singing his track Woman, the music took over as the actress and director pulled some intense dance moves at the bottom of the stage.
The former OC actor has also been supporting Harry’s career by wearing his merchandise while out and about in Los Angeles.
Harry and Olivia have been linked since meeting on the set of upcoming film Don’t Worry Darling, which features Harry and Midsommar star Florence Pugh, and which was directed by Olivia.
While many of the plot details are being kept under wraps, an official synopsis reads: ‘A 1950’s housewife living with her husband in a utopian experimental community begins to worry that his glamorous company may be hiding disturbing secrets.’
Harry is branching out from his incredibly successful musical career having clinched some major film roles, including in Marvels’ Eternals.
He has also recently revealed his newest venture, a beauty line called Pleasing.
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