I can understand the mainlands, as you have far more options in trrms of hideouts and where to retreat if needed. It seems the geographic restrictions of being on an island, even a relatively large one like Hispanola, would make it significantly easier for a search & destroy campaign to pin down the Maroons and cut off all avenues of retreat. Ditto for disrupting their food supplies - the farmer can run, but his crops can't.
Why was destroying these communities such a challenge to the colonial powers? What tactics and strategies did Maroon communities use to survive and fight back against their former enslavers?
By the time the British acquired Jamaica from the Spanish in 1655 there was already an established Maroon community in the mountains. As you can imagine, mountain hideouts are particularly hard to snuff out.
Rather than the Maroon fighting a defensive war against the British slavers they in fact took the offensive. They freed slaves in raids and forced multiple land and slave owners off their estates.
Furthermore fighting in the hills and mountains of inland Jamaica took a terrible toll on soldiers. In 1732 the British actually managed to take out the main Maroon base of Nanny Town but they managed to just melt back into the mountains and reorganise whereas the regular British troops succumbed to disease and drink.
A few years after this the Maroon's signed a deal with the British giving them nominal independence and that is how their culture survives to this day. They even became slave owners in their own right for a time!
I don't know much about the other islands, but in Puerto Rico, many slaves escaped inland to the mountains. The communities were often intermingled Africans and local natives. The natives were very helpful with survival as you can imagine. However, the island is small and slaves were more often recaptured. Slaves did not last very long in the Caribbean because of the harsh nature of sugar production and were either sold and shipped elsewhere or died of disease.
A good book that covers slavery in the Caribbean and specifically Puerto Rico is Sugar and Slavery in Puerto Rico: The Plantation Economy of Ponce, 1800-1850 by Francisco A. Scarano