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.
Yes, you can have a baby on the Sims 2 Bon Voyage.
You can't have a baby on sims 2 castaway for wii
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.