Gently scoop the cream off the top of the can of coconut milk. (discard remaining milk, or reserve for another use). Combine coconut cream and vanilla. Chill 1 hour. Add chilled cream mixture to a blender. Blend until whipped, about 30 sec.
While coconut cream is chilling, combine pineapple chunks, banana, and oranges in a medium bowl. Toss fruit with whipped coconut cream. Divide evenly among 4 small bowls. Sprinkle with coconut flakes.