The X Factor boss is currently enjoying a Christmas break in Barbados with his former lover, who he split from last year.
They originally got engaged in 2010, but Cowell later called off the union and branded the relationship a "big mistake".
Cowell is known to remain close with his ex-girlfriends and has previously taken Terri Seymour, Sinitta and Jackie St Clair on holiday.
He recently confirmed that he is dating former Baywatch star Carmen Electra, but insisted that they are not in an exclusive relationship.
"She's not my girlfriend. We're people who date. She's adorable, isn't she?" he said.
Photo gallery - Simon Cowell's ex-girlfriends: