If you haven't done so yet, consider which island you want to rent on: Oahu, Maui, Kauai, Hawaii Island (known as the "Big Island"), Molokai or Lanai. Oahu, the most visited island, is home to Waikiki Beach, Honolulu and Pearl Harbor, as well as small towns and rural areas. Maui gets the most humpback whales and has the famous and beautiful Road to Hana. The Big Island has the active volcano, the "Gold Coast" (Kohala) and Kona, and Kauai, "The Garden Isle" is popular with nature lovers and is home to the spectacular Na Pali Coast. Molokai is very laid back, almost completely rural and very traditional Hawaiian, while Lanai is the smallest and is popular with deer hunters and scuba divers.
Learn enough about your island destination and what you want to see and do there to determine the most convenient locations for your vacation rental.
Write a list of the things most important to you in a vacaiton home. For example, your list may include an ocean view, quiet location, pool, specific number of bedrooms, child-friendly or romantic, security system and furniture and appliance preferences. Most vacation rentals are fully furnished, including dishes and linens, but do ask. Since Hawaii has a large population of insects, you may also want to ask about window screens and pest control, especially when considering renting from a private party rather than a property management company.
Determine the amount you are willing to spend, including the rent, deposit and any other fees.
Search Hawaii-based newspapers online for vacation rental ads. Look specifically for the "vacation home" listings because other home rentals will mostly want tenants who plan to stay at least a year.
Post questions on Hawaii forums such as Hawaii Threads and Kona Web's "Visiting the Big Island" and look for tips, reviews and contacts.
Call to inquire about the vacation homes of most interest to you. Ask questions regarding your preferences and find out what their requirements of you would be. Generally a deposit is required to secure the rental and the rent is paid upon arrival.
Ask the property manager or homeowner to email additional pictures to you, if the ones on the site aren't sufficient. At the very least, view pictures of the home from the front and back that include some of the surroundings, as well as of the interior's rooms.
Consider the data you have gathered, and decide on the vacation home you wish to rent.
