Wailea-Makena Condo Market Guide For Savvy Buyers

If you are drawn to South Maui and want a smart, grounded way to evaluate condos in Wailea and Makena, you are in the right place. You might be balancing lifestyle goals with rental potential, or simply looking for a low‑stress second home. In this guide, you will learn how the market works, what to expect at each budget tier, how to evaluate rental rules and carrying costs, and how to quantify view and amenity premiums. Let’s dive in.

Wailea–Makena at a glance

Wailea–Makena is a master‑planned resort area known for high‑end condos, villas, and beachfront access. It generally trades at a premium to more mass‑market South Maui neighborhoods due to location, resort amenities, golf, and proximity to the ocean. Inventory is often tight, with winter months seeing more buyer activity and strong visitor demand for rental‑friendly properties.

You will see three main buyer profiles here: second‑home owner‑users, short‑term rental investors, and local residents upgrading lifestyle. Your priorities might be privacy and finishes, rental program terms and net yield, or a balanced option that does both reasonably well.

What your budget typically buys

Exact price bands change quickly, so compare recent closed sales before you decide. Here is what each tier usually looks like:

Entry/value tier

• Older studios or 1‑bedrooms in established complexes, sometimes with garden or partial ocean views.
• Compact footprints with simpler finishes and fewer on‑site services.
• Pros: lower entry cost, easier to rent to couples, simpler upkeep.
• Cons: more reliance on HOA, limited privacy, potential deferred maintenance in older associations.

Mid tier (most competitive)

• Renovated 1‑ to 2‑bedrooms with better finishes and partial to clear ocean views or quick beach access.
• Many units participate in rental programs.
• Pros: good balance of owner use and rental potential; solid resale demand.
• Cons: higher HOA fees with added amenities; meaningful premium for view and proximity.

Upper/luxury tier

• Oceanfront or strong ocean‑view 2–4 bedroom villas and penthouses, often with private entries and resort‑level services.
• High‑end finishes, concierge, secure parking, and elevated amenities.
• Pros: strongest lifestyle appeal and long‑term desirability.
• Cons: higher purchase price and carrying costs; smaller buyer pool at resale.

Wailea vs. Makena nuance

Wailea offers the widest variety of resort condos and amenity levels, along with on‑site services that appeal to both owner‑users and investors. Makena tends to feel more secluded, with fewer condo options but some very high‑end oceanfront product. If you value privacy and exclusivity, Makena may fit. If you want more choice, services, and rental program options, Wailea usually delivers.

How to read the market with confidence

Market conditions shift with interest rates, travel trends, and policy changes. Before you buy, review recent MLS reports for median price, days on market, months of supply, and sales‑to‑list ratios. Cross‑check broader trends with reputable Hawaii economic briefs. Maui also saw local impacts from the 2023 wildfires that influenced insurance and visitor patterns. A current, hyperlocal snapshot will help you decide on timing and offer strategy.

Rental rules and permitting: know before you buy

Short‑term rental rules vary by zoning, complex, and use type. Some communities allow nightly rentals and even offer on‑site programs. Others restrict rentals or require longer minimum stays.

Create a rental compliance checklist:

• Confirm whether nightly rentals are allowed for the specific complex and unit type.
• Review CC&Rs for owner‑use days, rental caps, program rules, and right of first refusal.
• Verify county permitting requirements for short‑term rentals and your intended use.
• Register and comply with State of Hawaii taxes for rentals, including TAT and GET.

If rental income matters to you, build these rules into your evaluation from the start. A condo that looks similar on paper can have very different revenue potential depending on its CC&Rs.

HOA fees and carrying costs

HOA fees typically cover landscaping, pool and common area maintenance, association insurance, water, waste, security, and reserves. Some associations include cable or internet. Review recent budgets and reserve studies to evaluate health and capital planning.

Watch for the following:

• Special assessments for roofs, exterior paint, seawall work, or major upgrades.
• Utility costs in Hawaii, which can be higher than the mainland average.
• Building insurance at the association level and additional coverage you may need.

A clear view of total carrying costs will keep your pro forma realistic.

Insurance and environmental risk

Coastal Hawaii properties can carry higher insurance costs. Underwriting has evolved in recent years, so pricing and availability may differ by complex and hazard exposure.

Check these risk factors for each property:

• Flood zone designation, tsunami evacuation zone, and coastal erosion risk.
• Wind and hurricane exposure.
• Wildfire and other natural hazards.
• Wastewater systems and any required upgrades.

Confirm lender insurance requirements before you write an offer. If a property falls within a higher‑risk zone, adjust your operating budget accordingly.

Financing and approvals

Financing options depend on your use case and the project’s approval status. Lenders often require larger down payments for investment properties, and specific condo projects may influence loan programs. If you plan to use FHA or VA financing, verify project approval early. Strong pre‑approval and familiarity with the project’s status will streamline your offer.

Valuing views and amenities

View and direct beach access tend to drive the largest premiums in resort markets. Instead of relying on rules of thumb, use a simple and repeatable method.

A practical approach:

1. Define your comparison set within the same complex or an immediately adjacent complex of similar quality.
2. Pull closed sales for the last 6–12 months to control for seasonality.
3. Calculate price per square foot for each sale.
4. Group sales by view band: oceanfront, ocean view, partial, golf, garden.
5. Compute the premium using averages across those groups.
6. Repeat for amenity sets, such as buildings with concierge and enhanced services versus basic common areas.

This method lets you quantify what you are paying for, rather than guessing.

Investor playbook: estimate yield the right way

If rentals are part of your plan, build a bottom‑up model. You can source nightly rates, occupancy, and RevPAR estimates from reputable short‑term rental data providers or local property managers.

Follow these steps:

• Establish a realistic annual occupancy band based on the complex and view class.
• Use market‑supported nightly rates and seasonality assumptions.
• Estimate gross revenue by month, then total for the year.
• Subtract HOA dues, property management commission, cleaning/linen, utilities, maintenance, supplies, taxes, and insurance to estimate net.
• Stress test with scenarios for soft shoulder seasons or increased expenses.

Keep your expectations conservative. A strong unit with clear views, beach access, and a guest‑friendly layout often delivers more consistent demand.

Seasonality and timing

South Maui demand often rises in winter. For investors, that can support higher seasonal rates. For buyers, it can mean more competition at certain times of the year. Review 12 months of closed sales and current inventory to plan your search and offer timing.

Due diligence checklist for condos

Use this list to stay organized:

• CC&Rs and house rules, including rental program terms and owner‑use limits.
• HOA budget, reserves, meeting minutes, and assessment history.
• Building insurance coverage and deductibles; your personal policy needs.
• Flood, tsunami, wind, and wildfire risk disclosures or maps.
• Project financing approvals and any pending litigation.
• Parking, storage, and on‑site amenities.
• Recent sold comps in the same complex by unit type and view band.

How we guide your search

You deserve precise, practical advice that fits your goals. We specialize in Wailea and Makena condos, blending hands‑on short‑term rental experience with a clear valuation approach. We help you quantify view and amenity premiums, verify rental rules, and build a realistic operating budget so you can buy with confidence.

When you are ready, we can walk you through recent closed sales in your target complexes, highlight hidden value plays, and set you up with local property managers and lenders who understand these projects.

Ready to explore the market, build a data‑driven plan, and see the best opportunities in Wailea–Makena today? Connect with Cory Mckim for a friendly, focused strategy session.

FAQs

What should I expect for HOA coverage in Wailea–Makena?

• Most associations cover landscaping, common areas, association insurance, water, waste, security, and reserves, with some including cable or internet; always verify the latest HOA budget and inclusions.

How do I know if a Wailea condo allows nightly rentals?

• Check the complex’s CC&Rs and any on‑site program rules, then confirm county permitting requirements and minimum stays for your intended use before you buy.

How big is the ocean‑view premium in Wailea?

• Quantify it by comparing recent closed sales in the same complex, grouping by view band, and calculating the average price per square foot difference.

What taxes apply if I run a vacation rental?

• Short‑term rental income generally requires registration and payment of State of Hawaii taxes such as TAT and GET; confirm current rules and filing steps before operating.

What insurance issues should I evaluate near the coast?

• Review flood and tsunami zones, wind and hurricane exposure, wildfire risk, and association policy details to understand total coverage needs and costs.

How do I estimate a condo’s net rental yield?

• Build a monthly revenue model using market‑supported rates and occupancy, then subtract HOA dues, management, cleaning, utilities, maintenance, taxes, and insurance.

Is Makena or Wailea better for a quiet second home?

• Makena often offers more seclusion with fewer condo options, while Wailea provides broader choice and services; the right fit depends on your privacy and amenity priorities.