Choose the island by price, not by postcard
Aruba, Punta Cana and Montego Bay carry far more rooms than St. Barts or Anguilla, and more rooms means softer pricing. If your heart is set on a quieter island, fly into the busy one and take the ferry or a short hop — you often save more on the room than the extra leg costs.
Travel the shoulder weeks
Late April through early June, and September into early December, give you the same water and the same sun at a fraction of peak pricing. Avoid the weeks bracketing school holidays and you can see rates fall by half.
Book the room wholesale
The same resort room sells at several prices at once depending on the channel. Member and wholesale inventory routinely lands 40 to 80 percent below the public rate on the very same room — identical bed, identical view, different price tag.
Spend on the trip, not the transfers
Pre-book an airport transfer rather than taking a taxi, eat one meal a day off-resort, and put the difference toward an extra night. A week nearly always beats five nights for value once the flight is paid for.