Drain pineapple, reserving syrup; add water to syrup to make 2 1/2 cups. Place 1 1/4 cups of syrup mixture in saucepan and bring to a boil. dissolve 1 package of jello in boiling syrup mixture. Add 1/2 drained pineapple and 1/2 cranberry sauce. Mix well and pour into a 9 x 13 dish. Chill until firm.
Beat cream cheese with sugar until smooth. Gradually beat in evaporated milk and vanilla. Soften unflavored gelatin in the cold water and heat to dissolve. Blend gelatin into cheese mixture, pour over firm Jello layer. Chill until firm.
Boil remaining 1 1/4 cup syrup mixture, dissolve remaining package of jello, add remaining crushed pineapple and cranberry sauce. Chill until room temperature. Pour very gently over cheese layer and chill until firm. Cut into squares.