Casino Royale by Ian Fleming (1953) — the first Bond novel, written at GoldenEye the winter after the house was built. Fleming's Jamaica — the heat, the rum, the particular quality of the light — runs through all the Bond books, but this is where it started.
Ian Fleming: The Man Behind James Bond by Andrew Lycett (1995) — the standard biography. Covers Fleming's time at Oracabessa in detail: why he built the house, how he worked, and how the place shaped the novels.
Rough Guide to Jamaica or Lonely Planet Jamaica — for practical coverage of the north coast beyond Oracabessa, including Ocho Rios, Port Antonio, and the interior.
The Children of Sisyphus by Orlando Patterson (1964) — Jamaican literary fiction set in Kingston, providing context for the island beyond the resort strip. Patterson became one of the most important sociologists of the Caribbean; this early novel shows where he started.