Combine sugar and water in small saucepan. Over medium heat, heat mixture until thick and caramel-colored, about 15 minutes Pour mixture into six 5-ounce custard cups to coat bottom of cups.
Preheat oven to 350°F. In large bowl combine eggs, sweetened condensed milk, pineapple, heavy cream and vanilla to mix well. Pour into prepared dish with caramel.
Place in large, deep pan. Pour enough hot water (not boiling) until water comes halfway up sides of dish. Carefully place pan in oven. Bake 30 minutes until flan is set. Remove from water bath. Let cool 10 minutes.
To serve, run thin knife around edges of flan; invert onto serving plates.
Or, cover and refrigerate until ready to serve.