The Mean Girls actress is reportedly considering an offer of $900,000 to bare all for the adult publication, after initially rejecting a previous offer of $500,000 from the magazine.
A source told Australia’s The Day newspaper: “Playboy has been asking her for years, but it’s only now she’s excited about doing it."
In addition to the naked shoot, Lindsay – who is dating DJ Samantha Ronson – has other ventures in the pipeline.
The 23-year-old star wants to take a break from acting to try her hand behind the camera.
She said: “I've been creating a bunch of shows that I've written treatments for and that I'm going to be producing - and that's more interesting to me."
However, Lindsay – who has previously had a guest role in US TV show Ugly Betty – does have her eye on an acting role that would see her reunite with Mean Girls actress-and-writer Tina Fey.
She admitted: “I would love to be on ‘30 Rock’. It’s a great show.”