In addition to @Renan's answer, the Bell Boeing V-22 Osprey has an internal payload of 20 000 lbs. Might take 2-3 trips, or 2-3 planes.
If there's no room to land a plane, and the island is too small for a reliable airdrop, you can also perform a low altitude parachute extraction.
The low-altitude parachute-extraction system (LAPES) is a tactical military airlift delivery method where a fixed wing cargo aircraft can deposit supplies in situations in which landing is not an option, in an area that is too small to accurately parachute supplies from a high altitude.
Note that the plane here doesn't actually land.
