Retirement in Hawaii, Part II: Earning Extra Income While Enjoying Island Life

I’ve written before about retiring in Hawaii on a budget, and that’s definitely doable. But what if you could retire in Hawaii and generate extra income at the same time? Given that the cost of living in Hawaii is higher than on the mainland, finding ways to supplement your retirement income can make island living even more enjoyable and sustainable.

One of the best ways to achieve this is by choosing the right property that offers rental income potential in a desirable location. Today, I’m highlighting a fantastic property in Waikoloa Village that provides a great opportunity for retirees looking to settle in paradise while generating extra income. I’m also giving you some tips for making additional income in other areas.

Spacious & Versatile Waikoloa Village Retreat – Ideal for Retirement, Multi-Generational Living, and Income Potential!

Imagine waking up in a home that perfectly balances comfort, space, and financial opportunity. This remarkable 6-bedroom, 5-bath, 3,950 sq. ft. residence in the heart of Waikoloa Village offers just that. With separate upstairs and downstairs living areas, connected by an interior staircase and additional exterior access, this home is ideal for multi-generational living, rental income, or simply a spacious retreat for family and friends.

Nestled on the uphill side of a peaceful street, this well-maintained property offers stunning views of the Kohala Mountains and a sense of serene privacy. Thoughtfully updated and move-in ready, it features a charming studio with a private bath on the lower deck—an excellent space for guests, a home office,  creative endeavors, or a one-person rental.

The main house is a single-level sanctuary with three spacious bedrooms, a bright and airy living room, a full kitchen, and a lanai for enjoying the island breeze. Downstairs, a fully independent unit awaits, featuring another three bedrooms, a generous living area, with a wet bar and refrigerator, and a separate entrance—yet still connected to the main home by an internal staircase. In Hawaii’s competitive rental market, properties like this are in high demand. Whether you choose to rent it long-term or as a hosted vacation rental on Airbnb, the potential for extra income is undeniable. If you’re curious about estimated rental earnings, feel free to reach out for more details.

Step outside to your own private oasis, where a Shangri-La-style hot tub awaits, surrounded by a beautifully landscaped and fully fenced yard. Whether you’re entertaining guests or unwinding under the stars, this outdoor retreat offers relaxation at its finest. And with Waikoloa Village’s prime location, you’re just minutes from pristine beaches, world-class resorts, shopping, golf courses, and dining.

This home is more than just a place to live—it’s a lifestyle investment. Whether seeking the perfect retirement retreat, an income-generating property, or a multi-generational haven, this unique residence offers endless possibilities. Learn more and schedule your showing today!

Why Waikoloa Village is Perfect for Retirement and Extra Income

Waikoloa Village is an excellent choice for retirees because of its cooler climate, relaxed atmosphere, and affordability compared to other areas of the Big Island. Additionally, it offers a variety of opportunities to generate extra income. Here’s how:

Hosted Vacation Rental – If your property qualifies, you can legally operate a hosted vacation rental. Many retirees choose to rent out part of their home to vacationers while still living on-site, providing a steady income stream without needing full-time property management.

Long-Term Rental Income – The demand for long-term rentals in Hawaii remains strong, particularly in sought-after areas like Waikoloa Village. Renting out a downstairs unit or an extra room can supplement your retirement income and cover monthly expenses.

Multi-Generational Living – Many retirees choose to move to Hawaii with family members. A property like the one listed above provides separate living spaces, allowing families to live together while still maintaining privacy. Adult children or extended family members may contribute financially, reducing overall living expenses.

Remote Work or Business Ventures – If you’re not ready to stop working entirely, Hawaii is a great place to launch a side business or remote work venture. Whether it’s freelance consulting, teaching online, or starting a small local business, the internet makes it easier than ever to stay connected while living in paradise.

Agriculture & Homesteading – For retirees who love gardening and sustainability, turning your property into a small homestead can provide additional income. Selling locally grown fruits, vegetables, or handmade products at farmers’ markets can be both fulfilling and profitable.

Renting Out Storage or Parking Space – If you have extra space on your property, you may be able to rent it out for vehicle storage, boat parking, or even as a workspace for local businesses.

Offering Personal Services – Hawaii’s thriving tourism industry means there’s always demand for personal services such as guided tours, wellness coaching, or even hosting cultural experiences for visitors.

Pet Sitting or House Sitting – Many people travel frequently, and offering pet-sitting or house-sitting services can be a lucrative way to make extra income in retirement while staying engaged with the community.

Teaching or Tutoring – Retirees with expertise in various fields can offer tutoring services to students, both online and in-person. Subjects like English as a second language, music lessons, or even Hawaiian cultural education are in high demand.

Art & Craft Sales – Many retirees in Hawaii channel their creativity into art, woodworking, jewelry-making, and more. Selling handcrafted goods at farmers’ markets, art fairs, and online can be both an enjoyable and profitable retirement pursuit.

Making the Most of Your Retirement in Hawaii

Moving to Hawaii for retirement doesn’t mean you have to live on a tight budget. By choosing the right property and exploring income-generating opportunities, you can enjoy all the beauty and relaxation the islands offer while maintaining financial stability.

The Benefits of Investing in a Rental Property

Real estate is one of the most reliable ways to generate passive income, and Hawaii’s booming tourism and rental market make it an excellent choice for investors. Owning a property with rental income potential means you can enjoy your home while still earning extra cash. Whether you choose a long-term rental or a vacation rental, here are some key benefits:

• Financial Security – Rental income provides a steady cash flow, which can help cover living expenses and unexpected costs.
• Property Appreciation – Hawaii real estate tends to appreciate over time, making it a smart long-term investment.
• Flexibility – You can rent out your property full-time, seasonally, or only when you’re traveling.

Understanding Hawaii’s Rental Regulations

Before investing in a rental property, it’s essential to understand the local laws regarding vacation rentals and long-term rentals. Some areas have strict zoning regulations, so working with an experienced real estate agent can help you navigate the legal landscape and find the right opportunity.

Creating a Retirement Lifestyle That Works for You

The key to a successful retirement in Hawaii is finding a balance between relaxation and financial stability. Whether you’re looking for a peaceful island retreat or an active lifestyle filled with business ventures, there are plenty of ways to make it work.

Retirement in Hawaii can be a dream come true, especially when you find ways to generate additional income. Waikoloa Village offers the perfect blend of affordability, amenities, and income potential, making it an excellent choice for retirees. Whether you’re interested in running a hosted vacation rental, renting out an extra unit, or exploring other income streams, there are many ways to supplement your retirement funds while enjoying life in paradise.

Are you ready to take the next step? Explore properties like the one featured above, and start planning your dream retirement today!