Kendall Jenner and Boyfriend Devin Booker Enjoy Tropical Getaway With Hailey and Justin Bieber

By Samantha Bergeson Sep 20, 2021 5:05 PMTags
Watch: Inside Kendall Jenner & Hailey Bieber's Double Date Trip to Jamaica

Double date alert!

After a luxe Mexican getaway in June, BFFs Kendall Jenner and Hailey Baldwin jetted off together again for a fun beachfront vacation—except this time, they invited their significant others. Justin Bieber and Kendall's NBA star boyfriend, Devin Booker, joined the model besties for a post-Met Gala and New York Fashion Week weekend in Jamaica. 

Hot off of Justin's sultry performance honoring Hailey at the Met Gala after-party, and Kendall's many runway walks, these A-listers relaxed by the lagoon at a tropical resort. According to a source, the quick trip was to a destination that "they have all been to before," in Jamaica, and the foursome went straight from New York for a three-day vacay. As of Sept. 19, they had all returned home to Los Angeles. 

"They were in private lagoon cottages near each other," an insider exclusively told E! News. "They had a great time swimming and wading in the lagoon. They did stand up paddling and spent a ton of time on the water. Even though it was raining, they loved the tropical weather and made the most of their trip. They stayed three nights before heading back to L.A. together on Sunday morning."
Inside Kendall Jenner's 2021 Italian Vacation

Hailey shared a series of Instagram pics on Sept. 19, showing herself and Justin cozying up by a waterfall, plus paddleboarding down a river and dancing in a rainstorm. Even though Kendall was not included in any of the snapshots, Kim Kardashian and Khloe Kardashian both "liked" the post, with Kim even commenting with three flame emojis.

This isn't Kendall and Devin's first romantic escape: The couple spent time in Lake Tahoe and the Hamptons, before sailing the Amalfi Coast in August. It's no wonder that even Kendall's family is smitten with Devin! 

"Him and Stormi [Webster] have an amazing relationship," Kendall gushed on The Tonight Show on Sept. 15. "She has the biggest crush on him, and I'm jealous sometimes. I'm like, 'Stop—can you guys not?'"

So, where will Kendall and Devin spend time together next? See pics from their Jamaican vacation below. 

Dive In

Kendall Jenner shared a pic of her bikini-clad behind before swimming in a lagoon. 

Soak Up the Sun

Hailey Bieber relaxed on a surfboard in a white hot bikini to soak up the atmosphere. 

Paddleboard Babe

Hailey spent the day paddleboarding down the river in a red bikini and matching bucket hat. 

Dancing in the Rain

Rain doesn't stop Hailey's parade! The model grabbed her drink and quickly posed in an Instagram video before running for cover on Sept. 19. 

Lounge 101

Kendall kicked up her feet in an Instagram Story, shared on Sept. 18. 

Float On

Devin Booker enjoyed some much needed R&R as he floated in the river. 

Blissfully Married

Hailey leaned back into her hubby Justin Bieber before a swim. 

Fashionable Date

Hailey wore a jaw-dropping outfit for dinner at the resort. 

Model Moment

Hailey showed off her physique in an artfully shot backlit portrait. 

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