Leo, 45, took a trip to Florida while his girlfriend, Camila Morrone, 22, is attending the Marrakech International Film Festival in Morocco. He enjoyed a night out with the supermodels at the nightclub, Ultraclub E11VEN.
He sat at a table with Kendall, 24, Bella, 23, and Gigi, 24, alongside 50 other guests from around 4 a.m. until 6 a.m. Kendall and Bella had partied at the venue on the previous night as well.
According to reports, the Once Upon A Time in Hollywood actor and the group was seen sipping E11even vodka and Don Julio 1942. Leo left the club with two male friends at 6 a.m. while Kendall and her gal pals left about a half-hour later.
On December 4, Kendall and Bella were spotted getting their suntans on in Miami during an afternoon at the beach. The catwalk queens were joined by a group of friends as they drank cocktails, relaxed on lounge chairs, and went jet skiing. Kendall's older sister Kourtney Kardashian was also seen briefly with the group.
The girls have also been chilling out with model BFF Joan Smalls all week. Kendall, Gigi and Bella have been in Miami to attend the Dior Fall 2020 Men's show.
This isn't the first time Leo has been seen at Art Basel. He also visited the annual art festival in 2015 where he hung out with and . This year's event is especially important for Leo as photographer David Yarrow created a special exhibit in honor of the environmentalist. David's photograph, “The Wolf of Wall Street I," features a black and white snap of the real-life Wolf of Wall Street, Jordan Belfort, who Leo portrayed in the 2015 black comedy blockbuster. Jordan stood alongside an actual wolf, money, and two models.
Leo and David collaborated on the project to help raise money for David's wildlife conservation efforts.
What are your thoughts on Leonardo, Bella, Kendall and Gigi partying together? Sound off in the comments below!