Kourtney - who is expecting a girl in July - revealed her growing curves while enjoying days by the pool and aboard a luxury boat during the trip to the Dominican Republic.
The Keeping Up With The Kardashian star spent plenty of time with her son Mason, two, and her partner Scott who were part of the large group soaking up the sunshine in the Caribbean.
Kourtney spent quality time splashing around with her son in the pool at their luxury villa on the island.
The mother-to-be, showed off her burgeoning bump in a tiny yellow and purple print bikini as she splashed around in the water.
Her son Mason looked adorable in a blue and white striped T-shirt and a pair of lobster-print shorts.
Despite being in the later stages of her pregnancy Kourtney couldn't resist picking up her son and walking around with him on the pool.
Kourtney was also seen chasing her son around the pool with the two-year-old having a wide grin spread across his face.
The pair also spent some time with Kourtney's sister Kim during their fun in the sun and the 31-year-old reality star displayed her curves in a Navy blue and white bikini.
Kim, who has been vocal about her hope for children of her own in the future was seen smoothing down Mason's hair while Kourtney carried him.
The family pictures come as Kourtney revealed she is keeping a list of possible baby names on her mobile phone, saying she is relying on modern technology to keep track of her ever-changing choices.
She told People.com: 'We always have our little list that I keep in my phone.
'I have my little list of names, and I cross it off one day and a new one comes. We definitely don't have the name. We're going back and forth.'
With two-year-old son Mason to care for, Kourtney admits this pregnancy has not been quite as easy as her first.
She explained: 'I think it's a little bit harder being pregnant when you have a toddler I'm chasing after. Last time I could nap more.'
Although she has been suffering from 'a little more morning sickness', the ‘Keeping Up With the Kardashians' regular is still managing to exercise.
She added: 'I've been active chasing after Mason. We go on walks all the time. Pushing the stroller is like carrying all these weights, and then [there's] the extra weight on my stomach, so it's good. It's fun.
'Last time I felt amazing the whole [pregnancy], and this time too. I feel really lucky.'
While Kourtney appeared happy to show off her curves in a daring tiny two-piece on her recent holiday, she also showed off how to cover a bump in a swimsuit during the family trip on the tropical island.
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The eldest Kardashian sister donned a leopard print bikini and a floor-legnth sheer white kaftan for a day at the beach with Scott and Mason.
She teamed the wild print dress with dangling earrings and an elaborate plait in her hair for a chic look for the sands.
It appeared that Mason was eager to indulge in some water sports too and the little tot was seen being put into a bright yellow lifejacket by Scott.
However the floation device appeared much too big for the little man and was ended almost at his knees.
While they spent most of the day doting on their son the pair did manage to steal some time away as they enjoyed a romantic stroll around the pool - away from their family.
The couple, who are expecting their second child together were seen sharing a warm embrace as well as a tender kiss by the side of the water.
But their moment of peace didn't last long and the couple were soon asked to join the whole family group for a series of cringe-worthy shots at the top of some steps together.
The group was seen holding up pieces of paper with cheesy grins on their faces and afterwards the family threw what they were holding up into the air.
On one night during the holiday Mason was seen enjoying a donkey ride with Kourtney not far behind.
The tot appeared to be delighted at riding the animal with the comfort of his mother close by and the whole event was caught on camera for the family's reality TV show.
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