i don't think you can take a pregnant sim on holiday
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A Sim won't go into labour when they are on vacation, but non pregnant Sims can conceive during the trip.
you need to have 2 young adult sims or adult sims who are "romantic interest" stage in their friendship to "woohoo". then you will have to wait until the baby is born.
You can't have a baby on sims 2 castaway for wii
Yes, you can have a baby on the Sims 2 Bon Voyage.
You don't need a housesitter when your sims go on vacation. When they leave and come back, it is the exact way they left it, including the same time. But if your sims have a baby or toddler, you need to get a nanny.