Jamaica is the most homophobic island in the Caribbean, with harsh anti-gay laws, even though there's a large local gay population.
Many all-inclusive resorts, notably the famous Sandals of Jamaica, allow same-sex couples, although they were forced to do so to be able to advertise in Britain. As part of the EU, Britain cannot condone discrimination in advertising. Hedonism II in Negril also allows gay travelers. So does the Grand Hotel Lido in Negril. Still, avoid open displays of affection -- such as handholding on the streets -- in Jamaica: You could be assaulted for trying it.
If you're desiring a gay trip to get some sun, forget Jamaica unless you want to stay deep in the closet. Puerto Rico, notably Old San Juan, is a friendlier destination, certainly South Beach (part of Miami Beach) or Key West, but definitely not Jamaica where intolerance of gays is most pronounced. Local gay activists have been killed or had their homes set on fire.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.