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Overnite stay on a round-trip (RT) ticket?

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We are going RT to the Caribbean. Regardless of airline, a change of planes will be required. The question - is it possible to book the RT to stay overnight in the change planes city on the out-going trip? To be more clear, it seems impossible to book online, except by booking the first part of the trip for day 1 and the continuing leg to final destination for day 2 as separate flights with a return on day X a few weeks later. This is substantially more expensive than the "normal" RT. Has anyone managed to include an overnite stay for the same price as without one? If so, helpful hints?
Thanks in advance.

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