Oahu Rentals by Owner

Question

My wife and I (mid 60s) are making our first trip to Hawaii in April. Initially hadn't planned on visiting Oahu, but decided to extend our stay to include 4 nights and 5 full days (9 pm return flight home) to explore the island. Looking for accommodations and have learned a bit about legal rentals and how rentals are restricted to designated tourist areas, with most of course, concentrated in Waikiki.

Just curious, are there any reputable "rent by owner" websites for Oahu/Waikiki? Got a recommendation to use a particular site for Maui and was able to book a tremendous condo in the location we wanted for much less than the traditional platforms like Airbnb and VRBO that I usually use.

Any advice greatly appreciated!

Answer

It's great that you're extending your stay to explore Oahu! While Waikiki is known for its tourist-friendly accommodations, there are also many great "rent by owner" options on Oahu, especially for those looking for a more local or personalized experience. However, as you’ve mentioned, there are restrictions on short-term rentals in many areas outside of the designated tourist zones, so it’s important to ensure the property you're interested in complies with local laws.

Here are a few tips and recommendations for finding reputable "rent by owner" properties in Oahu, including Waikiki:

Look for Local Platforms with Verified Listings: In addition to Airbnb and VRBO, there are some other rental platforms that specialize in local vacation homes and condos, which may offer better pricing or unique properties. For example:

Hawaiian Beach Rentals: This site offers vacation homes, condos, and beachfront properties throughout Oahu and other Hawaiian islands. It's often more locally focused and may have options outside the typical tourist-heavy areas.
Vacasa: Known for its personalized service and extensive list of properties, Vacasa often offers competitive pricing and may include properties in less-commercialized parts of Oahu.
Oahu Rent by Owner (Oahu RBO): This is a local platform where homeowners list their properties directly for rent. While less mainstream than Airbnb or VRBO, it can sometimes feature unique or more affordable options.

Check for Legal Compliance: Many rentals on Oahu are required to register with the city and county. Before booking, confirm that the property is legally permitted to operate as a short-term rental, especially in places like Waikiki where zoning laws are strictly enforced.
Read Reviews and Communicate Directly: Reviews can provide insight into the quality and reliability of a rental property. Reach out to the property owner directly for more details about the space, amenities, and location. This can help ensure you're getting exactly what you expect.
Consider Staying in Waikiki or Kaka'ako: If you're looking for convenience and easy access to beaches, dining, and shopping, Waikiki remains the best option. However, Kaka'ako is an up-and-coming area with cool cafes, art galleries, and a more local vibe, which could be worth considering for a rental outside of the tourist-heavy areas.

Lastly, as you’re booking for April, it’s a good idea to finalize your accommodation soon as Oahu is a popular destination, especially in spring. If you find a good deal, it might be wise to lock it in early!

Enjoy your time in Oahu, and don't hesitate to explore the island’s natural beauty, from hiking trails to pristine beaches. It’s truly a paradise!