But as he continued to work on his tan on the deck of his £270,000-a-week superyacht as it was docked off the coast of St Barts, Cowell was joined by a mystery blonde.
Commanding the music mogul's attention, the newest addition to Simon's harem of women was seen laying next to the the X Factor boss as they soaked up the sun on Wednesday.
Who's your new friend: Simon Cowell was seen hanging out with a mystery blonde on Wednesday in St. Barts
A new addition to the female entourage: Cowell enjoyed a lazy day in the sun on his super yacht with a blonde
The new girl on board: Sinitta gave Cowell's friend a kiss on the cheek as she said hello
While former pop star Sinitta, who dated Simon in the '80s, showed off her curves in a striped bikini.
Saying her hellos, the 44-year-old singer gave Simon's new friend a warm handshake and a kiss on the cheek.
Later that day, Simon's ex-fiancee Mezhgan Hussainy was also spotted on deck, lounging around in a white mini skirt.
King of his castle: Simon seemed to be in his elements as he took in the stunning scenery, and his equally gorgeous female entourage
In the pink: Simon's new female friend was wearing a pink fuchsia bikini and a leopard kaftan
Pulling faces: Simon pouts as he chats to his blonde pal
Keeping cool: Simon made sure he kept hydrated by drinking water during his sun session
'Lunch is for wimps': Sinitta has been tweeting about keeping up with her fitness regime on holiday
The 53-year-old is used to his luxury lifestyle by now, so it's no surprise that the plush boat is filled with lavish amenities for the group to enjoy.
A large hot tub can be found near the front of the boat, surrounded by comfy sofas and cushions, for Simon's harem of beautiful friends to recline on.
Waiting for the Titanic moment? Sinitta looked wistfully out to sea as she posed on the back of the yacht
Striped sensation: The 80s pop icon looked incredible in her navy and white two-piece