Devin Toner, Fergus McFadden and Jack McGrath have also signed new two-year contracts.
Dubliner Jennings has made 118 Leinster appearances over two spells since making his debut in the 2002/03 season and the St Mary's College man also featured in the 2008/09 Heineken Cup winning side.
He has played in 15 fixtures so far this season and has been capped on nine occasions by Ireland.
Jennings said: 'It is an exciting time for the province and I am delighted to re-sign with Leinster for a further three years.
'There is a determination within the group to push on and continue to improve. The aspirations of my team-mates, as well as the coaching staff, was a key factor in my decision to stay.
'Since re-joining the province in the summer of 2008 Leinster has gone from strength to strength on and off the park and I'm proud to be a part of a club that has such strong values and ambitions.'
Tullow native O'Brien is another successful product of the Leinster Academy and he follows in the footsteps of Cian Healy in committing his long-term future to the province.
O'Brien has made 47 appearances in all, scoring nine tries to date and he has earned four Ireland caps since making his international bow in November 2009.
O'Brien said: 'I am delighted to commit myself for a further three years to Leinster. I believe there is something very special about this club and with so many talented players at our disposal - and with the management team working well - I am confident that the great achievements of recent years can be matched or even maybe surpassed.
'While it was flattering to have interest from overseas, I desperately want to be part of the Leinster story for the foreseeable future.'
Toner said on his new deal: 'I think that the high competition levels within the squad this year have driven us all on and the upshot of that has been our recent good run of form.
'I have been very fortunate to have worked alongside the likes of Mal (O'Kelly), Trev (Hogan), Leo (Cullen) and Hinesy (Nathan Hines) in recent years and there's a really strong base within the squad where we're all trying to help each other and improve one another. I'm really pleased to sign up with Leinster.'
McFadden has also talked talked up future success for the province as he signs on for two more seasons: 'I am pleased to commit to my home province because I believe that this is the ideal environment to advance my personal and, most significantly, collective team ambitions.
'It's a really exciting time to be playing here and all of the players and staff share the same determination to push on and become a consistent force both in the Magners League and in the Heineken Cup.'
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