It shows the 35-year-old American rapper and 41-year-old Spanish singer move on from their past love interests by partying and snapping photos with a bevy of models.
"Messin' Around" appears on Pitbull's 10th studio album, Climate Change, which is scheduled for release this summer. The record also includes the singles "FREE.K" and "Freedom."
Pitbull and Iglesias previously collaborated on the hit songs "I Like It," "I Like How It Feels" and "I'm a Freak." The rapper had nothing but praise for his friend while discussing "Messin' Around" with Hot 95-7 in March.
"I gotta say thank you to Enrique Iglesias as always," he said. "He always shows so much love. More than anything, Enrique to me isn't only a great business partner, a great person to learn from, but he's also a standup human being."
Pitbull will kick off his Bad Man tour with Prince Royce and Farruko in support of Climate Change in June. Iglesias last released Sex and Love in 2014, which debuted at No. 8 on the Billboard 200 and includes the singles "Loco" and "Bailando."