Choosing between Wailea and Kā‘anapali for your Maui condo can feel like a coin flip. Both are iconic resort communities, yet the day-to-day experience, costs, and ownership realities can be very different. You want a clear path, whether your goal is a luxury retreat, a steady vacation rental, or a long-term hold.
This guide compares the two markets across price and product, HOA health, rental rules, financing, insurance, and lifestyle access. You will also get a practical due diligence checklist you can use before you write an offer. Let’s dive in.
Quick snapshot: Wailea vs. Kā‘anapali
Wailea in South Maui is known for master-planned luxury communities, newer or renovated properties, and resort-level amenities. You tend to see larger floor plans, upscale finishes, and a luxe second-home feel.
Kā‘anapali in West Maui offers a broader inventory mix, including many established resorts, older condo buildings, and a range of unit sizes. Entry points can be more varied, and the area has long attracted high visitor traffic.
If you picture polished resort living with premium pricing, Wailea may align. If you want more price options and strong vacation-rental demand in West Maui, Kā‘anapali can be compelling.
Who each market fits best
- Wailea: You prioritize luxury finishes, larger units, and resort amenities, and you are comfortable with higher purchase prices and HOA fees.
- Kā‘anapali: You value a wider range of price points, more small-to-mid-size units, and an established short-term rental scene, and you are prepared for older-building considerations.
Price and product: what to expect
Wailea generally commands higher pricing per square foot due to newer luxury product and limited supply. Kā‘anapali spans a wider spectrum, from studios and one-bedrooms in older buildings to premium oceanfront units in top resorts.
You will see more 2–4 bedroom offerings and resort-style penthouses in Wailea. Kā‘anapali has more studios and one-bedrooms, plus timeshare-style inventory and mid-size units.
At-a-glance comparison
| Factor | Wailea | Kā‘anapali |
|---|---|---|
| Typical price positioning | Premium, luxury-oriented | Wider range, including more moderate entry points and luxury options |
| Unit types | Larger 2–4 BR, high-end finishes, penthouses | Studios, 1–2 BR, some larger units, more timeshare/STR-oriented |
| HOA fee expectations | Often higher due to resort amenities | Varies, some older projects may have lower fees but higher maintenance risk |
| Short-term rental friendliness | Varies by complex, many luxury projects with defined policies | Many STR-oriented buildings, policies vary by association |
| Financing ease | Some non-warrantable buildings; jumbo and portfolio loans common | Mix of warrantable and non-warrantable; verify early |
| Buyer fit | Luxury second-home and premium vacation-rental investors | Value-seeking investors, established STR demand, varied price points |
HOA fees and building health
In resort areas, HOA fees often cover landscaping, pools, security, and shared amenities. Luxury Wailea communities typically carry higher monthly fees, which can be appropriate for the service level and grounds.
Older associations in Kā‘anapali may have lower baseline fees, yet they can face deferred maintenance or upcoming capital needs. Always review audited financials, reserve studies, recent meeting minutes, and the history of special assessments.
If the property is oceanfront, ask about seawalls and shoreline maintenance plans. Salt air accelerates wear, which can influence long-term budgets.
Short-term rentals and local rules
Whether you plan to use the condo as a short-term rental, a long-term lease, or a primary residence is often the biggest decision driver. Condo associations set their own rental rules, and some buildings prohibit short-term rentals or impose minimum stays.
Maui County and the State of Hawai‘i regulate transient accommodations, including registration and taxes such as the Transient Accommodations Tax and the General Excise Tax. Since 2023, rules and enforcement have been evolving across Hawaii. Confirm current county ordinances, building-level policies, and any area-specific restrictions before you buy.
If you plan to operate a vacation rental, request historical performance data from the seller or property manager, including average daily rate, occupancy, and net revenue after fees and taxes.
Income potential and seasonality
West Maui has historically seen strong visitor traffic, which benefits vacation rentals in Kā‘anapali. Wailea attracts high-end travelers who often pay premium rates, though occupancy can be more seasonal for certain properties.
To gauge income potential, ask for these metrics by unit type and view category:
- Average daily rate, occupancy rate, and revenue per available unit
- Management fees, utilities, maintenance, marketing, and tax remittance
- Comparable performance from similar nearby buildings
Financing realities for resort condos
Some resort or STR-heavy buildings are considered non-warrantable, which limits access to conventional, FHA, or VA loans. In those cases, you may need a portfolio or jumbo loan and a larger down payment.
Confirm the building’s owner-occupancy ratio, rental mix, and HOA financials with a lender who knows Maui resort condos. Align your financing plan with the building’s status before you go under contract.
Insurance, hazards, and maintenance
Insurance in Hawaii can be costlier than on the mainland, and availability has shifted in recent years. Flood insurance may be required in FEMA-designated zones, and wind or hurricane coverage can be a material expense.
The August 2023 Lahaina wildfires affected West Maui’s insurance landscape and local market dynamics. If you are considering Kā‘anapali, get up-to-date quotes and review hazard disclosures. In both areas, plan for oceanfront wear, salt-related corrosion, and proactive maintenance.
Lifestyle, access, and everyday convenience
Both areas offer resort amenities, beaches, and golf. Choose based on your routine. Wailea places you close to South Maui’s resort corridor and fine dining. Kā‘anapali keeps you near West Maui attractions and a centralized visitor hub.
Factor in driving patterns to Kahului Airport, grocery options, medical services, and any school or community needs if you plan to live on island part or full time.
A practical checklist for buyers and sellers
Use this list to vet a specific unit or building in Wailea or Kā‘anapali:
- Market comps and trendlines
- Pull recent closed sales, actives, and price per square foot for the building.
- Compare days on market and sales velocity.
- HOA and building health
- Review bylaws, house rules, meeting minutes, audited financials, and reserve study.
- Ask about special assessments, litigation, insurance coverage, and capital projects.
- Rental policy and income verification
- Confirm short-term rental eligibility and any minimum stay rules.
- Request historical rental statements and manager agreements.
- Regulatory compliance
- Verify county registration, state tax accounts, and any required permits.
- Financing
- Check warrantability with your lender and outline alternatives if needed.
- Insurance and hazards
- Obtain quotes for property, hurricane, liability, and flood; review FEMA and local hazard maps.
- Physical inspection
- Inspect for salt air corrosion, roof systems, pools, plumbing, and pest issues; evaluate shoreline structures when applicable.
- Cost to own
- Model HOA fees, property taxes, insurance, utilities, management, and capital reserves.
- Exit and liquidity
- Assess typical buyer profiles for the building and historical resale patterns.
How a local advisor adds value
In Maui’s resort condo markets, success comes from pairing local knowledge with clear systems. An experienced team will help you verify HOA health, navigate rental rules, confirm financing options, and source realistic rental performance data. That guidance can prevent surprises and protect your yield and lifestyle goals.
If you are weighing Wailea versus Kā‘anapali, connect for a focused strategy session and a unit-by-unit comparison. Contact Josh Jerman for a confidential consultation.
FAQs
What is the main difference between Wailea and Kā‘anapali condo markets?
- Wailea skews luxury with newer or renovated product and larger floor plans, while Kā‘anapali offers a broader mix of unit sizes and price points, including many STR-friendly buildings.
Are short-term rentals allowed in all Maui condo buildings?
- No, rental rules vary by association, and Maui County and state regulations apply, so confirm the building’s policy and current registration and tax requirements before purchasing.
How do HOA fees compare between Wailea and Kā‘anapali?
- Wailea’s luxury projects often have higher fees tied to resort amenities, while some older Kā‘anapali buildings may have lower base fees but potential for special assessments.
How did the 2023 Lahaina wildfires affect Kā‘anapali buyers?
- Insurance underwriting, availability, and costs may be in flux in West Maui, so obtain current quotes and review hazard disclosures and building insurance coverage.
Can I use conventional financing on a resort condo in Maui?
- It depends on warrantability; some STR-heavy buildings are non-warrantable, which can require portfolio or jumbo financing and higher down payments.
What should I review to estimate rental income for a unit?
- Ask for historical statements showing average daily rate, occupancy, and net revenue, plus management fees, utilities, and taxes, and compare with similar nearby units.
