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This is a great question and it's actually the very first question I asked myself when I started wanting to learn more about pirates. It can definitely seem strange from an initial perspective why some islands and areas became so important to various countries while others didn't and why some countries owned only a few small islands but not others... I mean they're all basically the same, right? Not exactly.

I think one key to really grasping this is to first understand what the Caribbean was actually like at this time on the ground level. Nowadays the Caribbean seems bright and fun and it's where people go on vacation because it's just so beautiful and sunny and gorgeous all the time. Well... that's not how it was in the 16th-18th centuries. In the early 17th century the Caribbean and American colonies were an extremely distant and remote colonial possession and they actually had a very small population. Disease was rampant and a good portion of the colonists and soldiers who went there died there. The weather was also not good for Europeans and it's not good for anyone who doesn't have access to 21st century air conditioning and pools at luxury resorts. It's incredibly hot and humid year-round and during the hurricane season lasting half the year, horrible storms erupt that can wreck ships or devastate entire settlements. In addition to that there were hostile natives in Central America and brutal slave rebellions and from the mid-16th century onward there were frequent English, French and Dutch privateering incursions into the Caribbean to brutally plunder and destroy Spanish possessions. If you didn't die from disease or shipwreck or other natural disaster you could meet a bloody and gruesome end through violence. It was a very scary and dangerous place and generally only desperate people would want to go there.

Now onto the wider history. Yes, it's true that from the early 16th century Spain was the only European country that had any colonial possessions in the Americas, but the Caribbean and Central America are a huge place. Venezuela, Columbia and Central America are each the size of Spain and Peru is twice the size of Spain. Cuba is the size of Italy and Hispaniola (the island that contains Haiti and Dominican Republic) is the size of Greece. After almost completely wiping out the native Taino inhabitants from the Greater Antilles through a truly brutal and systematic genocide, the Spanish barely even settled many of those places and the small settlements they did set up were often abandoned as colonists migrated to more prosperous colonies in Cuba and the mainland or were forced to flee because of French and English privateering raids. Many colonists also wanted to be closer to the immensely wealthy silver mines of Potosí in Peru. From the mid-16th century these were manned by vast numbers of enslaved Indian laborers and produced vast wealth that was shipped to Spain aboard the annual Spanish treasure fleets. These mines were so lucrative that over time they led to vast amounts of inflation in Europe that permanently changed the price of precious metals because there was so much silver pouring into the coffers of Habsburg Spain to fund their massive wars and expenditures in Europe.

The first Northern Europeans to venture into the Caribbean were French and English privateers in mid-16th century and they quickly found that the vast shipments of precious metals being transported combined with the scattered and often poorly defended nature of Spanish settlements, often provided a very lucrative reward for a few daring raids. The very first of these was the French privateer Jean Fleury who in 1523 who captured three Spanish treasure galleons in the Atlantic filled with Aztec gold returning from Hernan Cortes' conquest of Mexico. For the first time, other European powers now became truly aware of the vast wealth coming from the Americas and over the next decade dozens of other French corsairs would follow Fleury's example and begin making voyages to the Spanish Caribbean and South America to plunder and raid the sparse and often poorly defended Spanish settlements. In 1533 another French corsair captured the largest annual Spanish treasure ship off the coast of Brazil and from that point on Spain began an organized convoy system to protect their most valuable treasure ships from these sorts of attacks. Despite that, a century later in 1628 the Dutch captured almost the entire Spanish treasure fleet off the coast of Cuba, but this was extremely rare. In the 1540s the French sacked numerous Spanish towns and settlements in the Caribbean and by the 1550s they almost had free reign to plunder the Caribbean, frequently devastating Spanish settlements in the Greater Antilles and causing them to be abandoned. In 1555 the French Huguenot privateer Jacques de Sores sacked and destroyed Havana and multiple other large Spanish towns. All this had the effect of bringing the badly needed supply of treasure from the Americas to Spain to a standstill.

In the 1560s in the wake of their huge successes against the Spanish, French Huguenot Protestants tried to found a French colony called Fort Caroline in Florida but the Spanish decisively destroyed this in 1565 and soon after the entire French fleet was destroyed in a hurricane. Then France itself erupted into religious civil war and the primarily Huguenot Protestant corsairs who had been the driving force behind these depredations against Spanish Catholics in the Caribbean were distracted at home fighting against French Catholics.

However, the Spanish were not granted a respite for long, as taking advantage of this opening English privateers under John Hawkins and later Sir Francis Drake began partially replacing the French as the main terrorizers of the Spanish colonies. Hawkins and his fleet were defeated by the Spanish in 1568 off the coast of Mexico but his protege Francis Drake made many very successful raids in the 1570s and 1580s in conjunction with French corsairs. He famously captured a treasure laden Spanish mule train crossing the Isthmus of Panama in 1573 and later he crossed into the Pacific and captured a Spanish treasure ship off the coast of Peru in 1579. In 1585 he launched a huge expedition that sacked the town of Santo Domingo in the Caribbean and on the other side of the Atlantic he also won sweeping victories against the Spanish at Cadiz and the defeat of the Spanish Armada in 1588. However, in the 1590s his career began to falter and Drake suffered a number of defeats and unsuccessful raids against the Spanish before dying himself in the Caribbean.

After this the Dutch started to become more prominent as raiders against the Spanish as part of their ongoing rebellion against Spanish rule in the Netherlands called the Eighty Years' War. I've already noted how the Dutch privateers Piet Hein and Witte de With captured nearly the entire Spanish treasure fleet off the coast of Cuba in 1628, and by the 1630s they had invaded and colonized large parts of Portuguese Brazil which they held until 1661. The Dutch also occupied the island of Curacao off the coast of Venezuela in 1634. At this same time, the English also began attempting to colonize various small, sparsely settled or uninhabited islands like St. Kitts in the Lesser Antilles and New Providence Island about 100 miles off the coast of Central America in 1631 (not to be confused with the much later colony of Nassau in the Bahamas), but the Spanish cracked down on these efforts since they were being used as a base for English privateers against the Spanish and destroyed the English settlements in St. Kitts in 1629 (though they came back in 1639) and New Providence in 1641. Another island the English occupied in 1625 was Barbados on the easternmost point of the Lesser Antilles. This was more successful and the Spanish weren't able to expel them. Just for reference, this was obviously being done at the same time as the English were also just beginning to colonize New England in North America in 1620.

However, the most important non-Spanish influence in the Caribbean during the early 17th century was the French just as they had been in the early 16th century. After helping to establish a settlement on St. Kitts in conjunction with the English in 1624, they established a base in northern Hispaniola in 1625. To give an idea of just how sparsely populated most of these nominally Spanish owned islands were, Alexandre Exquemelin who documented the French colonization in his book The Buccaneers of America published in the late 17th century wrote that when the French reached northern Hispaniola and found it fertile and filled with wild horses, cattle and pigs that could be hunted for their hides, they decided to make the island of Tortuga opposite it their base and only had to chase away a ten or twelve Spaniards living there. There was virtually no one living around there except a few seasonal hunters. Then no Spaniards harassed them at all for a year and a half until a Spanish force probably numbering a few hundred men at most drove the ~50 Frenchmen (my own estimates) off Tortuga to take refuge hunting in the forests of Hispaniola, but they were able to quickly come back after the Spanish sent most of their forces away, and retake the island. The Spanish periodically recaptured and then abandoned Tortuga in the coming years, while the French simply retreated to the unpopulated backwoods of northern Hispaniola and waited for the Spanish to leave before going back.