A High Wind in Jamaica by Richard Hughes (1929). Not set in Negril but the most gripping novel about Jamaica's past as a crossroads of piracy, empire, and childhood innocence. Hughes's story of children captured by pirates has an unsettling moral depth entirely at odds with its adventure-story surface. Read it for the Jamaica that existed before the beach resorts.
The Harder They Come by Michael Thelwell (1980). The novelisation of Perry Henzell's classic film, following a young man from the countryside who arrives in Kingston with dreams and ends up a fugitive outlaw. Thelwell's prose captures the sound of Jamaican English and the brutal economics of the island's music industry. The best introduction to the culture that produced reggae.
Wide Sargasso Sea by Jean Rhys (1966). Set mostly in Jamaica and Dominica in the years after emancipation, this is the story of Bertha Mason — the first Mrs Rochester of Jane Eyre — told from her own perspective. Rhys's prose is incandescent; the Jamaican landscape, its heat and wildness, becomes a character. Essential reading for understanding the island's colonial history through a personal lens.
My Brother by Jamaica Kincaid (1997). A memoir by the Antiguan-born writer about returning to care for a brother dying of AIDS. Kincaid is forensic about the Caribbean's relationship with its colonial past and with death; the book ranges far beyond its ostensible subject. A short, concentrated read that stays with you.