Vacation Rental Ownership Tips from Oahu’s North Shore

If you’ve visited the Hawaiian Islands, you understand its beauty and cultural prestige. You might have also realized Hawaii certainly knows how to market itself well. Why not use this to your benefit? If you’re like me and you’ve decided to make Hawaii your home, and have also decided to invest in real estate, then a North Shore vacation rental might be for you.

Army Beach - Haleiwa, HI

Army Beach – Haleiwa, HI.

Considering the many Oahu locations, I determined famed North Shore Oahu was best. The iconic coastline offers world-class surf and an authentic small town tropical experience for all who live and visit.

Unlike Waikiki’s hotel and retail saturated neighborhood, North Shore’s industry is nearly nonexistent. As a result, a tranquil retreat is provided for residents and vacationers alike. North Shore delivers a truly unique and well sought after Hawaiian experience for all!

Vacation Rental Lanai - Haleiwa, HI

Vacation Rental Lanai – Haleiwa, HI

Based upon my experience, I’ve come up with tips to consider if you’re interested in buying and operating vacation rental investment property in Hawaii:

1. Conduct realistic analysis on vacancy rates of similar vacation rentals in the immediate area. Determine what spectrum of booking rates are being offered in vacation rentals as close to your ideal property as possible. Use websites like VRBO, Homeaway, Airbnb, and Craigslist as research tools when “crunching the numbers.”

2. Your goal should be to ensure vacation rental income will more than cover all the associated operational expenses to include your mortgage, vacation rental insurance, taxes (Hawaii’s near 14% with GE and TAT), professional tax and accounting, renovations, regular cleaning, repair fund, and replacement of regular expendable items (towels, linens, glassware, soap, etc.).

3. Plan to add “sizzle” features during the renovation that will distinguish and highlight your property from the competition to help you ensure your calendar is booked.

Vacation Rental Interior - Haleiwa, HI

Vacation Rental Interior

When it comes choosing and preparing a vacation rental property:

4. Confirm the location is desirable! Vacation rentals must be near attractions whether natural or man-made. Within walking distance is preferred. Being in a quiet area, having a great view, and delivering an authentic local experience are key components to a successful vacation rental operation. Property with ocean views and close proximity to the beach will be able to maximize profits.

5. Invest in a well-constructed property. Install quality furnishings and amenities. Many times vacation rental properties are neglected by owners who don’t make the effort to provide quality furnishings in an effort to cut costs. To make your property stand out, try adding higher quality furnishings. You might find that a vacation rental that is in great shape with good amenities will be treated with more respect than those without. Offer special items such as surfboards, snorkel gear, and full set of kitchenware. Make installation upgrades like granite countertops, entrance keypad for keyless entry (no need to hand over keys if none are needed!), and Hawaiian décor.

6. Have professional pictures taken of your property. Focus on the vacation rental’s best features.

7. Hire a Property Manager. Or if you plan to manage yourself, get familiarized with vacation rental management software and systems. Do research and choose one of the many rental management software suites available. Your systems should be able to handle online advertisement, bookings, transaction recording, rental agreements, guest correspondents, guest and management calendars, cleaning and maintenance schedules. In today’s online environment there should be no need to make calls or meet your guests, everything can be done online via management systems and email. Vacation rental ownership can be seamless even as the property owner-manager.

8. Make an effort to build relationships with owners in the area surrounding your vacation rental. This way there’s always someone around to keep an eye on your property. It’s also a way to share guest leads with other vacation rental owners. You can always solicit advice and management tips from their experience as well.

9. Provide elite customer service to every guest. Ensure your reviews are great! As vacation rental owners and managers, your goal should be to develop long-term relationships with every guest. Exceed their expectations so they’ll book your rental for years to come. Happy guests will be motivated on their own to leave your advertisement website or page great reviews.


When going through the process of searching for a great vacation rental property, these tips are the essential ingredients to vacation rental ownership success!