The hotel heiress posted a photograph of herself in Havana with the caption “Cuba baby!”
British model Naomi Campbell was also spotted in the capital of the communist island.
Their visits follow the historic rapprochement between the United States and Cuba announced in December that has eased travel restrictions.
It coincided with a tour by former UN secretary-general Kofi Annan, who is seeking to boost Colombian peace talks hosted by Havana.
Hilton’s great-grandfather Conrad Hilton traveled to Cuba in 1958 to open a hotel. But the hotel was nationalized by Castro in 1960, along with other American-owned properties on the island- AFP