1/12 Montego Bay, Jamaica
Montego Bay stays at a reasonable price for the entire year. The weather is great and there are plenty of water sports and other activities to do. Montego Bay also has the Caribbean's largest and busiest airports, so flights here are usually direct and cheap compared to other smaller islands. The beautiful beach is lined with small hotels, restaurants, and bars. A 3-star resort here starts at $70 a night for two people.