Columnar jointed rock masses (CJRMs) have a complex network structure and, therefore, present a great challenge to geotechnical engineering design. A series of triaxial compression tests is performed on artificial CJRM specimens subjected to a confining pressure of 5 MPa, considering various pore pressures (pw=0 MPa, 2 MPa, and 4 MPa). In this work, the influence of the joint dip angles and pore pressure on the anisotropic strength, deformation, and failure modes of the CJRM is investigated. The anisotropic characteristic stresses, strength parameters (c and φ) and elastic modulus of the CJRM specimens show a U-shaped pattern with increasing joint dip angles (β), while Poisson’s ratio changes inversely. The elastic modulus has a stronger anisotropy than Poisson’s ratio. Moreover, with increasing pore pressure, the characteristic stresses decrease, while the anisotropy of stresses and deformations increases. Finally, three failure modes of CJRM specimens with different joint dip angles are observed under triaxial compression conditions.