Concerning the issue of performing more than one `Umrah on the same journey, there is neither prohibition nor obligation to it. However, neither the Prophet (peace and blessings be upon him) nor his righteous companions ever did it. That is why some scholars dislike it and see that it is not recommended, unless one offers `Umrah once for himself and again on behalf of others. However, other scholars see nothing wrong in making multiple `Umrahs on one visit, even if they are all for oneself.
Dr. `Abdur-Raziq M. Fadl, of Al-Azhar University states that: Some Muslim scholars see that it is permissible to make multiple `Umrahs while one is staying in Makkah, especially if the rest of the `Umrahs after the first are offered on behalf of other people, for example, a late father or brother. There is still a single point I want to stress in this concern. I would like to remind every Muslim that making multiple `Umrahs, no matter for how many times, does not substitute for Hajj, nor does it exempt one from the obligation to perform Hajj whenever he can afford it physically and financially.
Some scholars maintain that it is not recommended to make multiple consecutive `Umrahs on one journey—that is, the person leaves Makkah towards At-Tan`eem, where he puts on ihram and then makes another `Umrah and repeats it several times. These scholars base their view on the fact that the Prophet (peace and blessings be upon him) and his Companions never did this. Rather, the Prophet (peace and blessings be upon him) performed four `Umrahs in four years, each one on a separate journey.
Nevertheless, we cannot generalize this ruling to include all cases. This means that if `Umrah is made for a certain purpose, then it is all right to make it several times on the same journey. Hence, a Muslim can perform `Umrah for himself. Then he can make another `Umrah on behalf of his father, then he can make another one on behalf of his mother in one journey. But it is not commendable to perform `Umrah more than once for oneself on the same journey. However, if it happened that one did it, it would not be more than disliked, according to the view of some scholars.
Hence, if one intends to make one `Umrah for themselves and the rest on behalf others, then there is nothing wrong on all levels. But if you want to perform four `Umrahs for yourself, then you are free to choose one of the views mentioned above; that is, either to do it according to those who legalize it, or to refrain from this according to those who dislike it, as it never occurred in the Prophet’s lifetime.