Contemporary Project and Portfolio Management Information Systems (PPMIS) have embarked from single-user, single-project management systems to web-based, collaborative, multi-project, multi-operational information systems which offer organization-wide management support. The variety of offered functionalities, along with the variation among each organization needs and the plethora of PPMIS available in the market, make the selection of an appropriate PPMIS a complicate, multi-criteria decision problem. The problem complexity is further augmented since the multi stakeholders involved in the evaluation/selection process cannot often rate precisely their preferences and the performances of candidate PPMIS on them. To meet these challenges, this paper presents a PPMIS selection/evaluation approach that applies a hybrid group decision making method based on TOPSIS and Intuitionistic Fuzzy Sets (IFS). The approach considers the vagueness of assessors' judgments when evaluating PPMIS and the uncertainty of users when they judge their needs. The approach is demonstrated through a case study aiming to support the Hellenic Open University to select a suitable PPMIS.