The singer, 19, stopped by Cindy and husband Rande Gerber's house and posed for photos with the two youngsters.
"I was chilling at my house after I got my tonsils taken out and my sister had a friend over to hang," Presley, 14, posted on Instagram alongside the snap of himself and Harry.
"This guy knows how I feel."
In the image, Harry is sticking is tongue out while holding his throat while Presley smiles for the camera.
In another shot, Harry is seen with his arm around Kaia, 11, who looks delighted to be posing with the heartthrob.
It's not the first time Harry has made a house visit for a fellow celebrity – in November of last year, he went to Johnny Depp's home with his bandmates to perform for the actor's 13-year-old daughter Lily-Rose.
Kaia also seems to be a big fan of Taylor Swift, who recently dated Harry Styles.
"So great 2 see u & take our kids 2 such a gr8 concert! @TaylorSwift," Cindy recently tweeted.
Meanwhile, Harry has revealed that he has no problem with Taylor writing songs about their short-lived relationship.
Taylor, 23, often pens chart-topping hits about her break-ups — and now Harry has said he fully expects her to use their past romance as inspiration.
"It would be hypocritical for me to say she couldn't do it because everybody writes songs based on personal experience," the 19-year-old told US Weekly.
Rande Gerber and Cindy Crawford with their children Presley Walker and Kaia Jordan
"I can't say I'd have dated someone less famous to avoid it," he said. "At least she's a great song writer!"
Harry split from Taylor in early January after a few months of dating. It might be his most high-profile relationship to date, but the boyband star said he doesn't think being in the public eye makes a difference when it comes to dating.
"I think it's people, you like people for who they are, so I couldn't say I want to date someone less famous because of the hassle. You like who you like," he told the publication.
"I think relationships are hard enough, so I think you have to completely ignore everything from the outside."