Justin Bieber Jets To Caribbean With Hailey Baldwin And Family, Kourtney Kardashian Posts Cryptic Note

Page Mackinley

After a successful and hectic 2015, Justin Bieber has jetted off to the Caribbean with his siblings, close pal and model Hailey Baldwin, and his father Jeremy and his partner.

While spending Christmas in his native Canada with his family and friends, both Jeremy and Justin shared pics (the Biebs also shared Snapchat videos) while on route to the Caribbean.

Apart from Jazmyn and Jeremy's partner, it was an all-boys' affair in Canada until Hailey and her pal arrived on Boxing Day. The "Sorry" superstar shared a sweet shot of himself with the blonde model, captioned, "Hailssssssssssss."

Jeremy's tweets and a Snapchat story indicated the group arrived at their no doubt idyllic destination on December 27. Fan sites shared Justin's Snapchat videos online.

Justin Bieber via Snapchat: pic.twitter.com/1RBQFa83kF

— JustinBieberCrew.com (@JBCrewdotcom) December 26, 2015

Based on social media posts from other holidaymakers on the island, Hailey, Justin, and his family are believed to be in the Dominican Republic in the Caribbean.

That's Bieber. Lol. pic.twitter.com/I6w4XpbcyK

— Jason Diamond (@imjasondiamond) December 27, 2015

On Sunday, the Biebs updated his fans with an Instagram photo of himself on a beach enjoying the sun with his younger brother and sister -- Jaxon, 6, and Jazmyn, 7 -- Hailey, 19, her pal, and another child.

Alongside the snap, the singer wrote, "Sandcastlekings @richwilkersonjr," which refers to a spiritual self-help book written by Pastor Rich Wilkerson Jr., who is tagged in the caption.

Justin Bieber fans will remember the pop icon and Hailey jetted to the Parrot Cay private island resort in the Turks and Caicos islands just before last New Year's Eve to ring in 2015, along with pals.

The Canadian star has previously spoken of his friendship with Hailey, noting that she and their mutual friends, models Gigi Hadid and Kendall Jenner, have been a great support system during his dramas.

"They are literally the sweetest girls," Justin revealed to i-D magazine for a recent interview.

He added, "They have the best hearts. They care about me in the same way that I care about them. When people say mean things about them, I get defensive and when it happens to me they get defensive."

The magazine told Justin that when they spoke to Hailey she promised the singer would be "back, bigger and better than ever."

The 21-year-old duly told i-D, 'Hailey, isn't she just the best, ever?'

Last year, Baldwin said of Justin to E! News, "I've known him since I was so young -- since I was like 13 --- and we've just been good friends over the years. We have just stayed close and there's nothing more to it than that."

The Biebs also shared a Snapchat video of Jaxon dismantling a sandcastle on the beach, which Justin had to prompt him to do.

Justin Bieber via Snapchat: pic.twitter.com/iskm6D1Cko

— JustinBieberCrew.com (@JBCrewdotcom) December 27, 2015

He also posted a video of the little boy playing with Hailey.

Justin (rickthesizzler): What a guy - via Snapchat #JustinBieberUpdates pic.twitter.com/PWOqoc3CVt

— Bieber Updates (@OLLGofTORONTO) December 28, 2015

Justin Bieber via Snapchat: pic.twitter.com/mkfa01ZY7Y

— JustinBieberCrew.com (@JBCrewdotcom) December 28, 2015

Other pictures of the "Sorry" singer with Hailey, Jeremy, and his partner also popped up on Justin's Snapchat yesterday, and showed them on off-road transports.

Justin's (rickthesizzler) photo - via snapchat #JustinBieberUpdates pic.twitter.com/w8dSLXyEJG

— Bieber Updates (@OLLGofTORONTO) December 27, 2015

Justin's (rickthesizzler) photo - via Snapchat #JustinBieberUpdates pic.twitter.com/bd59qKGHBr

— Bieber Updates (@OLLGofTORONTO) December 27, 2015

Meanwhile, back in La La land, Kourtney Kardashian -- who is said to having non-serious, fun romps with Justin -- set tongues wagging on Sunday after she posted a cryptic Instagram message of a quotation.

The screengrab reads, "The prettiest smiles hide the deepest secrets. The prettiest eyes have cried the most tears, and the kindest hearts have felt the most pain."

Kourtney posted the shot with a blue heart emoji.

Naturally, the rumor mill is speculating whether the 36-year-old mother-of-three is ex-relationship with the father of their children, Scott "Lord" Disick. He was caught cavorting with his former girlfriend, Chloe Bartoli in the South of France in July. The couple split shortly after. TMZ previously claimed Kardashian and Disick are only amicable for the sake of their kids.

Another part of the grapevine wonders whether Kourt is missing her young lover, Justin Bieber?

Into the mix of all this, Page Six claims Kourtney and Scott's turbulent relationship is not as done as some media outlets previously reported.

"It goes back and forth depending on the day of the week. She's been letting him see the kids and they've been trying to work on [possibly getting back together], but nothing has been decided," a source told the gossip column.

"They're still his family," said the source.

The insider added that Disick is not on the Kardashian-Jenner radar any more and is no longer spoken of.

"When he's not there, no one's thinking about Scott. They literally don't talk about him. Everyone has their whole thing going on. . . I don't think anyone cares if [Scott and Kourtney] are together or not," said the source.

Notably, Disick wasn't present at the family's Christmas party, although it's said he was invited.

.@kourtneykardash shops as @ScottDisick is MIA for Xmas. Is it over btwn the parents-of-3? https://t.co/VOnsPO0odL pic.twitter.com/Sn6onAS3pe

— X17online.com (@x17online) December 25, 2015

As for Disick's thoughts on Kourtney and Justin's alleged tryst, the "Lord" isn't apparently deeply unhappy about it.

A sources says, "The Bieber thing was definitely a bump in the road. He was super pissed about it...when that came out. Hearing she's partying with this A-list superstar with way more money than you, whether [it's romantic] or not, it's embarrassing!"

Disick recently shot a music video with R&B singer Chris Brown and the pair are reportedly keeping each other sober.

Kourtney Kardashian Shares Cryptic Instagram Quote Amid Scott Disick Reunion Rumors https://t.co/xlGIxXDSan pic.twitter.com/lHuh4jB5Q0

— Inquisitr Showbiz (@IQShowbiz) December 27, 2015

For his part, the Biebs is likely still basking in the ongoing afterglow of great feedback his Purpose album is receiving. The singer has three songs in the top ten of the official singles charts of Australia, the U.K., and the U.S. With the latter two countries, he has three songs in the top five.

After an incredible comeback in 2015 and his Caribbean break, the pop prince should be ready to have it even larger in 2016.

All the albums that have hit no. 1 on the #Billboard200 this year https://t.co/cK04dpBeLU pic.twitter.com/YfYLibGxkJ

— billboard (@billboard) December 28, 2015

Justin is also featured on today's Cosmopolitan Snapchat story, "The 15 Best Albums of 2015". #JustinBieberUpdates pic.twitter.com/ac56sCr6wz

— Bieber Updates (@OLLGofTORONTO) December 27, 2015

The Best Albums of 2015

Let the debate begin. https://t.co/DzEirA9UG1 pic.twitter.com/d1CBmdBHXZ

— Complex (@ComplexMag) December 1, 2015

[Images via Instagram]