Jennifer Aniston and Her Cabo Crew Lounge Poolside

Jennifer Aniston kicked off her annual holiday vacation in Cabo on Monday with a day at the pool with her friends. The actress was seen relaxing in a black bikini while chatting with Justin Theroux, Jimmy Kimmel, and John Krasinski. On Tuesday John and Justin took a few ATV's out for a spin in the sand after lounging poolside with Howard Stern's wife, Beth Ostrosky, and Jimmy Kimmel's wife, Molly McNearney.

John and Jimmy are no strangers to Jennifer and Justin's Cabo trips, as both have been welcomed as guests on the couple's Mexican vacations over the years. Hopefully Jennifer will be able to get caught up on her R&R as the award season buzz surrounding her latest film, Cake, seriously starts to heat up. She has already been nominated for the Golden Globe for best actress in a drama, and she will face off against some fierce competition at the award show on Jan. 11.