The 48-year-old Titanic star has been living it up in St Tropez, with the pals being snapped in the coastal town on Monday.
Leonardo opted for a casual look, wearing a plain white T-shirt and beige shorts.
He accessorised his outfit with a black bag, beige cap, flip-flops and a silver necklace.
The actor seemed to be engrossed in his phone as he walked with security.
Tobey also dressed down for the outing as he wore a black T-shirt and dark patterned shorts. He carried a pair of black sunglasses and wore a black cap.
One of the women accompanying Leonardo and Tobey was English model Neelam Gill.
She looked very chic as she stepped out wearing a leopard print maxi dress.
The Vogue star carried her belongings around in a bright green bag, while also holding onto a mini orange handbag.
One person who was noticeably absent from the lavish trip was Leonardo’s rumoured flame Gigi Hadid.
The rumoured couple are reportedly engaging in a ‘no-strings attached situationship’ and are keeping things ‘open and fluid’ in order to balance their busy work schedules.
Leonardo and Gigi sparked romance rumours back in November, when they were reportedly getting ‘flirty’ at dinner together in New York. Neither of them has spoken out about the rumours.
Just last month, the pair were spotted at nightclub boss Richie Akiva’s party in the Hamptons as they further fuelled romance rumours.
However, they both arrived and left the party separately.
Since then, a source has revealed neither of them wants to settle down as they opened up about their romance.
‘Leo and Gigi have a friendly, no-strings ”situationship” right now,’ the insider told Us Weekly.
‘[They] travel so often so it’s best for them to keep their relationship open and fluid. Neither one of them wants to settle down at the moment.’
Sources previously told Entertainment Tonight that the Hollywood duo were ‘very much into each other’ but were ‘mindful’ of the model’s split from baby daddy Zayn Malik.
‘Gigi has been trying to keep things low-key with their relationship. They are trying to keep things private and not show too much PDA while out together,’ the source said.