Cylindrical roller bearings (CRBs) are key components of mechanical transmission systems. The internal load distribution and stiffness (LDAS) have significant effects on the bearing fatigue life and vibrations. It can also affect the precision, reliability, and service life of mechanical transmission systems. Due to the external loads applied on the bearing, the flexible deformations of rings and rollers would be produced, which will change the LDAS. To study the LDAS of CRB, an improved quasi-static model of CRB is established. The flexible deformations and waviness of rings and rollers are considered. An analytical calculation method based on the Newton–Raphson method is conducted to obtain the LDAS. The results show that the radial force, speed, and waviness can greatly affect the LDAS; the flexible deformations of rings and rollers increase with the increments of radial force and speed; the internal load distribution is also greatly affected by the waviness, which leads to the uneven load distribution; the radial stiffness decreases with the increment of waviness amplitude; and the waviness order has a slight effect on the radial stiffness.