The 21-year-old model and 28-year-old rapper enjoyed some Art Basel festivities with friends following Jenner's appearance in the 2016 Victoria's Secret Fashion Show.
Jenner and A$AP Rocky were spotted together Friday at E11EVEN Miami nightclub, according to People.
The couple spent the night dancing with Jenner's sister, Kylie Jenner, whose boyfriend, Tyga, performed at the venue.
"[Kendall and A$AP Rocky stayed] side by side [the whole evening]," a source told the magazine.
Jonathan Cheban, a longtime friend of Jenner's half-sister Kim Kardashian, shared posts of Jenner from the party. The model turned heads in a sleeveless lace top and sequined miniskirt.
E! News reported that Jenner and A$AP Rocky left the club together in the same car before stopping at a Walgreen's. They exited the store separately but were later seen entering a hotel around 4:30 a.m.
Jenner and A$AP Rocky were seen together again at DJ Khaled's birthday party Sunday at LIV nightclub.
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Sources told People the pair were acting "very flirty" as they cozied up at a table for hours.
Jenner previously dated One Direction singer Harry Styles, and was linked to rapper Tyler, the Creator over the summer.
She and A$AP Rocky have been spotted together at various points over the past months.
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