How long can I stay in Jamaica without obtaining a visa and do I need to buy a round trip flight?

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The Consulate General of Jamaica says you'll need a return ticket and how long you might stay is determined at entry:

Requirements For Entry Into Jamaica

All visitors are required to be in possession of a national passport or other acceptable travel document establishing nationality and identity, and bearing a photograph. The passport or other travel document must be valid for the period of intended stay in the island. Visitors are also required to show evidence of sufficient funds to support themselves during their stay and be in possession of a return or round trip ticket to another country to which they are admissible.

Nationals of certain countries require, in addition to travel documents, an entry visa. This is normally issued, on application, by a Jamaican Consular office.

The decision in respect of admission and length of stay in the country rests with the Immigration Officer at the port of entry in Jamaica. This applies whether or not a visa is a prerequisite for entry.

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