Answer: Kailua, located on the windward side of Oahu, generally experiences slightly different weather patterns compared to Waikiki, which is on the leeward side of the island. In mid-December, both areas are in Hawaii's wetter season, but the windward side typically receives more rainfall due to trade winds pushing moisture up the Koʻolau Mountains.

Answer: Choosing between Kailua and The Kahala really depends on what kind of experience you're looking for on Oahu. Both options have their unique advantages, so I'll break down some pros and cons to help you make a decision.