Should You Purchase A Long-Term Rental Or Short-Term Rental Property

Should You Purchase A Long-Term Rental Or Short-Term Rental Property

  • Chelsea Dimin
  • 10/15/22
Are you considering whether to purchase a short-term or long-term rental property on Maui? Both options allow for pass-through income to pay for what has historically been an appreciating asset while building equity. Both options also provide owners with a vacation home on Maui. Check out the pros and cons of each to find out which option is the best fit for you.

What’s The Difference?

In Maui County, a short-term rental is a room, apartment, house, condominium, beach house, hotel room, suite, or similar living accommodation rented to a guest for less than 180 consecutive days. Short-term Rental properties must be permitted and licensed. A long-term rental property allows tenancy for a minimum of 180 consecutive days, requiring an initial six-month lease period that can then be extended month to month.

Owner Stays

Property owners can stay in their long-term rental property less frequently, between the minimal six month lease periods. Owners can stay in short-term rental properties on demand by simply blocking their reservation calendar in advance. It’s always a good idea to check on any limitations or fees a property management company may impose for Owner Stays. 

Rental Rates

There is a limited supply of long-term rental housing on Maui and increasing demand. The effect of this low supply and high demand results in increasing market rental rates that can help pay for monthly carrying costs and possibly even generate income for a long-term rental property.

Operating Expenses

Long-term rental properties have lower operating expenses when tenants are required to pay for their own utilities such as electricity, wifi/cable, trash and water. This reduces a property owner’s carrying costs to property taxes, Homeowners Association/Maintenance Fees, landscaping, and principle and interest on a mortgage if they financed the purchase.

Property Management Fees & Services

The State of Hawaii requires all rental properties to have a designated on-island contact to manage an investment property and to be available for tenant emergencies. A full-service property management company can market the property, find and screen tenants, create lease agreements and manage insurance requirements, provide transparent accounting, and handle repair and maintenance requests while protecting the owner’s investment. Hawaii Life Vacations is a full-service property management company that charges 10% of the long-term gross monthly rent rate to cover marketing, property management and accounting. Compare this to the short-term rental property management rate of 25% of the short-term rental gross rents. Other property management companies charge up to 35% of gross rents for short-term rental property management, so it’s a good idea to compare services and fees amongst several property management companies.

Maintenance & Repairs

Long-term rental properties generally require less maintenance and repairs because single tenancy over a long period of time causes less wear and tear than multiple guests that stay in a short-term rental property every several days. This is reflected in the 10% long term rental property management fee versus the average 25% short-term rental property management fee that Hawaii life Vacations charges.

Property Taxes:

One of the biggest differences between owning a long-term rental versus a short-term rental is the Maui County property tax rates. You can view the difference in tax rates in the chart below. You can find more information about Maui County property tax rates and classifications by clicking here.
When considering purchasing an investment property on Maui, ask a property management company to provide a breakdown of estimated expenses for you. Contact me to request an estimated pro formas for a specific property that you may be considering to buy.
A breakdown of property expenses such as property management fees, monthly maintenance/Association fees, property taxes, deep cleaning fees, utilities, and repairs/maintenance can help guide you with your purchase.

The Why?

What is most important to you when purchasing an investment property? The bottom line? An existing vacation rental history? Location? A Fixer Upper that you can easily upgrade and then rent out? Or maybe it is having a move-in ready destination that you, your friends and family can stay in when you visit Maui. Depending on your motivation, ask a reputable property management company to provide you with rental projections and a list of their services for both long term and short-term rental property management so you can decide which type of rental property best suits your needs.
Contact me for more information about purchasing a short-term or long-term rental on Maui and to find out about full-service property management services.
Chelsea Dimin

Chelsea Dimin

Realtor® Broker

About The Author

Chelsea Dimin stands at the pinnacle of Maui's luxury real estate, consistently ranking among the top 1% of agents in sales volume. Chelsea specializes in oceanfront property and vacation homes and has over 17 years of expertise in real estate, business development, and advertising sales.

Originally from Milwaukee, Wisconsin, Chelsea holds degrees in Journalism and Spanish from the University of Wisconsin Madison. Her career journey led her to Los Angeles in 2006, honing negotiation skills representing top brands in digital media and advertising sales. In 2010, she joined New York Magazine's digital publication,, as the West Coast Advertising Sales Account Executive. In 2014, Chelsea embraced Maui's allure, obtaining her real estate license and collaborating with a local developer. As a Realtor Salesperson, she played a key role in transforming vacation rental estates into profitable ventures, attracting a global clientele.

Acquiring her Broker license in 2017, Chelsea made history in January 2023, becoming the first female Realtor to list and sell a $32 million dollar home in Makena, as reported by the Wall Street Journal. Today, Chelsea guides buyers in realizing their Maui dream homes. Known for tenacity and creativity, she forges connections, assesses needs, and delivers strategic results. Chelsea's signature is creating opportunities, leveraging a global network for off-market deals and win-win negotiations.

Clients appreciate Chelsea's commitment to staying informed, providing updates on values, market trends, and recommendations. Beyond real estate, Chelsea enjoys an active lifestyle, engaging in surfing, yoga, barre classes, mountain biking, beach runs, jungle hikes, and waterfall adventures with her husband Tim and beloved pitbull, Lulu.

“My mission is to exceed your expectations so that you never hesitate to refer your friends, family or coworkers to me in the future.”

Work With Chelsea

Are you interested in buying or selling a home on Maui? Contact me to tap into my local knowledge and global connections. My mission is to exceed your expectations so that you never hesitate to refer your friends, family or coworkers to me in the future.

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