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What You SHOULD Know About Wailea & Makena Resort CONDO Rentals

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The Beverly Hills of Maui,

Known as “The Beverly Hills of Maui,” Wailea Beach Villas is one of the island’s most sought-after luxury vacation rental properties.

If you’ve ever dreamed of owning a piece of paradise on Maui’s sun-kissed south shore, Wailea and Makena are two names you’ve probably heard before. It’s no surprise, then, that resort rental condos in Wailea and Makena are in high demand. For buyers and investors alike, they offer the best of both worlds: a turnkey vacation retreat you can enjoy yourself and rent out when you’re not using it.

Here’s everything you need to know about the resort rental condos in Wailea and Makena:

Table of Contents

WAILEA & MAKENA AT A GLANCE

Wailea and Makena set the standard for elevated island life on Maui’s most coveted coastline.

Located along Maui’s scenic southwestern coast, around 35 minutes away from Kahului Airport, Wailea and Makena are neighboring communities that define luxury living in paradise. While both offer breathtaking ocean views and a refined island lifestyle, each has its own unique character and appeal.

About Wailea

Wailea is a 1,500-acre resort community known for its curved golden beaches, five-star resorts, high-end shopping, and championship golf courses. A favorite among vacationers, second-homeowners, and retirees, Wailea is synonymous with luxury island living. The area attracts travelers looking for the complete resort experience – sun, golf, dining, pampering – all within walking distance.

About Makena

Just a short drive south is Makena, which feels quieter, more remote, and even more exclusive. Known for its ultra-private estates and dramatic lava rock coastline, Makena captivates those who are after privacy, natural beauty, and a connection to Maui’s quieter side. For buyers looking for a vacation or second home that feels like a true escape, Makena is the spot.

Beaches That Set the Bar

Wailea and Makena have exceptional beaches that show the natural beauty and diversity of South Maui’s coastline.

In Wailea, you’ve got a front-row seat to some of Maui’s best beaches:

In Makena, the beaches are a bit more rugged, expansive, and untouched. Here, dramatic landscapes and fewer crowds are alluring come-ons.

Recreational Activities That Define Luxe Living

Wailea is a playground for golf lovers, tennis enthusiasts, spa aficionados, and upscale shoppers. Top-rated courses include Wailea Gold, Emerald, and Blue. The community also offers access to the Wailea Tennis Club, award-winning spas such as Spa Grande and Willow Stream, and a vibrant culinary scene. For upscale retail experiences, The Shops at Wailea features a curated mix of designer labels, including Louis Vuitton and Bottega Veneta, as well as local boutiques and fine art galleries.

Makena, on the other hand, is a haven for those seeking privacy, natural beauty, and understated luxury. While there are no major shopping centers or golf clubs within Makena itself, residents are just minutes from Wailea’s upscale amenities, allowing residents both tranquility and access.

WHAT ARE RESORT RENTAL CONDOS?

Enjoy the flexibility of a vacation-ready retreat that generates income when you’re away.

Resort rental condos are privately owned condominium units located within or near resort-style developments. They offer a mix of luxury living and rental income potential, making them different from typical condos or single-family homes.

Instead of being used year-round, these properties are set up for short-term stays and are often rented to vacationers when the owner isn’t using them. This makes them a great option for people who want a place to enjoy themselves while also earning some income from their investment.

Rental Condos are Turnkey, Comfortable, and Loaded with Amenities

One of the biggest perks of a resort rental condo is that it’s turnkey, which means that everything’s ready for you or your guests to walk in and relax.

Here’s what rental condos typically offer:

And unlike a cramped hotel room, these condos feel more like a home with the added bonus of being in a beautiful, high-demand vacation destination.

Who buys resort rental condos?

Resort rental condos appeal to a wide range of buyers, but most fall into three categories:

BENEFITS OF OWNING A RENTAL CONDO IN WAILEA & MAKENA

Owning a resort rental condo means having a low-maintenance, high-reward investment.

If you’ve been thinking about investing in a vacation property, Wailea and Makena offer a sweet spot between luxury, lifestyle, and long-term value.

Here’s why so many buyers are drawn to owning a rental condo in this part of South Maui:

  1. BENEFIT: Strong rental income potential

    Wailea and Makena are two of the most sought-after destinations on the island, which means high nightly rental rates and steady demand year-round, especially during peak seasons. Whether you’re listing your unit for a few weeks or several months at a time, these areas consistently attract vacationers willing to pay for premium accommodations.

  2. BENEFIT: Access to world-class amenities

    As an owner, you and your guests enjoy all the high-end resort perks, from sparkling pools and beach clubs to concierge services, golf courses, and spa access. These added features not only enhance the guest experience but also boost your rental appeal and value.

  3. BENEFIT: Tax perks and property appreciation

    There are notable tax advantages to owning a rental condo, including potential deductions for mortgage interest, property management fees, maintenance, and depreciation. Plus, Wailea and Makena real estate tends to appreciate well over time, thanks to limited inventory and strong buyer demand.

  4. BENEFIT: Lock-and-leave convenience

    One of the biggest perks of condo ownership is the low-maintenance, “lock-and-leave” lifestyle. With on-site management or local caretaking services available, you don’t have to worry about upkeep while you’re away.

  5. BENEFIT: Using it when you want

    A top perk of owning a rental condo is flexibility. Use it for your own Maui getaways, then rent it out when you’re not on the island. The flexibility of owning a Wailena or Makena vacation rental allows you to enjoy paradise while still generating income and making your property work for you.

CHALLENGES AND CONSIDERATIONS

Owning a rental condo in Wailea or Makena can be a rewarding experience but like any investment, it comes with a few things to think through.

If you’re considering buying a Wailena or Makena vacation rental, here are key points to keep in mind:

  1. CONSIDER: Local regulations and zoning

    Maui has specific short-term rental regulations and zoning laws, especially in areas outside designated resort zones. Not every condo can legally operate as a short-term rental, so it’s important to double-check that the property is properly zoned and permitted before you buy. Working with a knowledgeable and experienced agent can help guide you through what’s allowed and what’s not.

  2. CONSIDER: Property management and service fees

    Unless you live on the island full-time, you’ll likely need a property management company to handle bookings, guest services, cleanings, and emergencies. While this takes a lot off your plate, it does come with management fees, which is typically a percentage of your rental income. It’s a worthwhile trade-off for peace of mind, but be sure to factor it into your budget.

  3. CONSIDER: HOA dues and special assessments

    Most resort-style condos in Wailea and Makena are managed by homeowners associations (HOAs). These associations typically handle exterior maintenance, landscaping, and amenities, which are funded through monthly dues and occasional special assessments. If the Wailea or Makena rental condo you’re considering has an HOA, it’s important to review the association’s financials and rules to avoid any surprises.

  4. CONSIDER: Market competition and occupancy

    Wailea and Makena are popular, but they’re also competitive vacation rental markets. Occupancy rates can vary depending on the season, marketing strategy, and guest reviews. A well-maintained, well-furnished condo in a great location will always stand out but you’ll want to go in with a clear plan to stay competitive year-round.

  5. CONSIDER: Maintenance, insurance, wear and tear

    With frequent guest turnover, expect more routine maintenance and general wear and tear than you’d see with a long-term rental or private home. You’ll also need to budget for insurance, cleaning, and repairs. Staying proactive with upkeep can go a long way toward protecting your investment and keeping guests happy.

SHORT-TERM VS. LONG-TERM RENTAL POTENTIAL

When it comes to owning a rental condo in Wailea or Makena, one of the first decisions you’ll want to make is how you plan to use it: as a short-term vacation rental or as a long-term lease. While both strategies have their perks, it’s really about what fits your goals, lifestyle, and how hands-on you want to be.

  1. Income and occupancy expectations

    Short term: In the Wailea and Makena resort areas, short-term rentals tend to offer higher nightly rates, especially during peak travel seasons and holidays. This means greater income potential overall but also more frequent guest turnover and a need for active property management.

    Long term: Long-term rentals offer a steady, predictable income stream with fewer vacancies and less daily involvement.

  2. Involvement and turnover

    Short term: You or your management team will handle bookings, guest check-ins, cleaning, and maintenance between each stay. This can be a great option if you’re comfortable with a more active approach or working with a full-service property manager.

    Long term: Lower turnover (often one tenant for six months or longer) means less wear and tear, fewer logistics, and more time to just enjoy your investment.

  3. Licensing and rental rules

    Short term: In Maui, short-term rental properties are subject to county regulations, zoning restrictions, and permit requirements. Some condos are in resort-zoned areas where short-term rentals are allowed, while others may restrict rentals to longer terms (30 days or more). Always check with the condo association and Maui County ordinances to confirm what’s permitted for a specific property.

    Long term: Long-term rentals typically don’t require the same level of permitting and often face fewer legal hurdles. They’re generally more straightforward when it comes to compliance but may also come with less flexibility in how you use the unit personally.

  4. Flexibility for personal use

    Short term: Offers maximum flexibility if you’d like to use the property yourself from time to time. You can block off your preferred travel dates and rent it out the rest of the year.

    Long term: Once a tenant is in place, your access is limited until the lease term ends.

WHAT TO LOOK FOR WHEN BUYING A RENTAL CONDO

The more you know about what makes a great resort rental, the better positioned you are to invest wisely.

When you’re shopping for a vacation rental condo in Wailea or Makena, it’s easy to fall in love with ocean views and lush surroundings. But if you’re buying as an investment, it’s important to take a step back and run the numbers because this is about building wealth, not just collecting sunsets.

Here are the key things to focus on before making a decision:

  1. Rental history and income projections

    Before you get too attached to any unit, take a close look at its rental history (especially if it’s currently in a short-term rental program). Ask for past income statements and look at average nightly rates, occupancy trends, and seasonal fluctuations. Then compare those numbers to your projected expenses. A good investment doesn’t have to be a gold mine overnight, but it should show long-term potential for both income and appreciation.

  2. Property management options

    Whether you live on-island or not, having the right property management team makes all the difference. Some condos come with on-site management and front-desk service, while others give you the freedom to hire an independent manager or manage it yourself.

    Each approach has trade-offs. On-site teams often charge more but make things seamless for guests. Off-site managers may offer more flexibility and competitive rates. Either way, be sure to factor management fees into your monthly budget.

  3. HOA rules and rental restrictions

    Not every condo in Maui is eligible for short-term rentals and not every complex wants them. You’ll need to confirm that the unit is zoned and permitted for short-term occupancy (less than 180 days) and then dig into the HOA rules. Some associations allow nightly rentals but impose limits on how often or how long, while others may have restrictions on pets, parking, or noise that can affect guest satisfaction.

  4. Interior condition and upgrade potential

    A well-maintained unit will naturally earn better reviews and higher rental income. When evaluating a condo, it’s important to look beyond the decor. How old are the appliances? Has the unit been renovated recently, or will you need to make improvements before listing it? Don’t forget to account for ongoing wear and tear as well since vacation rentals take more of a beating than owner-occupied homes.

    And if the unit needs a facelift, be realistic about renovation costs. Many experts recommend budgeting at least 20% more than expected, just in case.

  5. Location within the resort

    Two units in the same complex can have a vastly different rental performance based on their position. Oceanfront units or those with full water views usually command premium rates and book up faster. Ground floor units may appeal to families with kids while upper floors may be quieter and offer better views. Also consider how close the unit is to the pool, parking, beach access, or potentially noisy common areas.

FOR OWNERS THINKING OF SELLING THEIR CONDOS

If you’ve been toying with the idea of selling your Wailea or Makena condo, this might be the nudge you’ve been waiting for. The current market is showing strong signals that now could be a great time to list. With limited inventory, steady demand, and increased interest from mainland and international investors, well-positioned condos in South Maui are getting serious attention.

WHY NOW MIGHT BE THE RIGHT TIME

Let’s face it. Buyers love Maui and that’s not changing anytime soon. But right now, low inventory and motivated buyers are creating a great market for sellers.

SECURE YOUR WAILEA OR MAKENA VACATION RENTAL TODAY

Buying a rental condo in Maui is as much about strategy as it is about sunshine. When done right, your Wailea or Makena vacation rental can be both a relaxing retreat and a smart long-term investment.

If you need help narrowing down the best rental-friendly communities or condos in Wailea and Makena, Realtors Dennis and Martha Rush are just a call or message away. Their expertise extends to beachfront properties, ocean view properties, golf properties, and legacy properties on Maui.

Explore your options today. Give Dennis & Martha a call at 808.280.0788 or send them an email.

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