The Messenger of Allah ﷺ performed four umrahs. The first was the Umra of Hudaybiyyah. The second was the one they had agreed upon for the following year. The third was from Jiranah. The fourth was the one he combined with his Hajj.
اعتمر رسول الله ﷺ أربع عمر: عمرة الحديبية، والثانية حين تواطئوا على عمرة من قابل، والثالثة من جعرانة، والرابعة التي قرن مع حجته.
Abu Dawud (1993), Tirmidhi (816), Ibn Majah (3003), and Ahmad (2211) all narrated it, and Ibn Hibban (3946) and Hakim (3/50) graded it sahih, all of them by way of Dawud bin Abdul-Rahman Attar, from Amr bin Dinar, from Ikrima, from Ibn Abbas, and he related it.Tirmidhi said, "The hadith of Ibn Abbas is a hasan gharib hadith. Ibn Uyayna narrated this hadith from Amr bin Dinar, from Ikrima, that the Prophet ﷺ performed umrah four times, without mentioning in it from Ibn Abbas."Then he traced it with a chain going back through Saeed bin Abdul-Rahman Makhzumi, from Sufyan bin Uyayna, with his chain of transmission.I say, Dawud bin Abdul-Rahman Attar was deemed reliable by Abu Dawud and others, and he is among the narrators found in all the major collections, so his addition is accepted.