Photographed arriving in the singer's home country on a commercial flight on Tuesday, ASAP - real name Rakim Mayers - was seen in the airport wearing a white T-shirt, patterned trousers and a face mask.
Rihanna, 32, was herself seen travelling to the Caribbean nation last week, although the Umbrella singer took a private jet.
The two have known each other for years and occasionally worked together, but have ignited romance rumours in recent months.
The romance talk started when they walked the red carpet at The Fashion Awards in London a year ago.
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