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Throughout Western history, second home ownership has traditionally been viewed as the privilege of the wealthy, and the practice has spanned the centuries. For example, the Roman elite decamped to their multiple properties according to season and whim; Henry VIII of England is said to have owned around 55 palaces when he died in 1547; and in the United States, the extremely wealthy Vanderbilt family owned multiple enormous second homes by the late 1890s. In Scandinavia, the earliest second homes were owned by the nobility and landed gentry in the 1700s, and were found predominantly in the countryside and along the coast.

In the Caribbean, it was initially the local elite who owned second homes in the hills and spent the summers there in order to ...

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