Trying to choose between Wailea and Makena for your Maui second home? You are not alone. Both sit along the same stunning South Maui coastline, yet they deliver very different lifestyles and ownership experiences. In this guide, you will see how they compare on property types, lifestyle, access to amenities, ownership costs, risks, and what to verify before you buy. Let’s dive in.
Who thrives in Wailea vs. Makena
Wailea at a glance
Wailea is a master-planned resort district known for convenience and a rich mix of hotels, luxury condos, golf, dining, and retail. If you want a turnkey condo with on-site services, easy access to beaches, and strong short-term rental demand, Wailea is built for that rhythm. Many buyers choose Wailea for predictable management, proximity to activities, and guest-friendly infrastructure.
Makena at a glance
Makena sits just south of Wailea and feels more secluded, with lower-density shoreline, large private parcels, and a natural, rugged backdrop. If you want privacy, estate-scale living, and big shoreline vistas with fewer neighbors, Makena tends to deliver. The inventory leans toward single-family estates and private club properties, with far fewer condo options than Wailea.
Property mix and price landscape
Wailea property types
Wailea’s real estate is anchored by high-end and ultra-luxury condominiums across resort communities and boutique complexes. Entry points for luxury condos often begin in the low millions, and rare beachfront or penthouse units can reach the mid to high single-digit millions or more. There are pockets of single-family homes and estate lots nearby, ranging from several million into the high single-digit or low double-digit millions depending on location and views. Liquidity is generally stronger for condos that allow short-term rentals, thanks to steady guest demand and professional management options.
Makena property types
Makena’s inventory skews toward multi-million dollar estates and estate lots, including trophy oceanfront properties that can trade in the high single-digit millions to tens of millions. There are fewer condos and they often command premium pricing for privacy and oceanfront positioning. Transaction volume is lower than Wailea. Unique estates can attract a targeted buyer segment and may take longer to sell.
Note on pricing: South Maui is dynamic at the ultra-luxury level and values change quickly. Always confirm current MLS data and request a local comp set before negotiating.
Amenities and lifestyle tradeoffs
Beaches and coastal access
Wailea offers multiple smaller, protected beaches with paved access, nearby parking, and lifeguarded areas at popular spots. Beach access is especially convenient for condo owners and guests. Makena is home to expansive sand at Oneloa, commonly called Big Beach, and the adjacent Little Beach. The setting is dramatic and less developed, with fewer facilities. Big Beach is known for a stronger shorebreak that can be hazardous for casual swimmers. You can review safety and park details on the Hawai‘i Department of Land and Natural Resources page for Makena State Park.
Golf and clubs
Wailea is famously golf friendly, with multiple championship courses at Wailea Golf Club offering resort and public play. That makes it easy for you and your guests to book tee times. In Makena, golf access is more often through private clubs or nearby courses, sometimes with membership requirements. If club access is important, confirm membership availability, initiation fees, and guest policies early in your process.
Dining, shopping, and services
In Wailea, dining, retail, spas, and concierge services cluster within a short drive or walk of many properties. Property management and housekeeping vendors are plentiful. In Makena, you will drive to Wailea for fine dining, groceries, and routine services. Medical and hospital services are in Kihei and Kahului, typically 20 to 45 minutes away depending on your exact address.
Privacy vs. convenience
This is the core lifestyle choice. Wailea maximizes convenience and walkability around resort hubs. Makena maximizes seclusion and uninterrupted shorelines. Choose based on whether you prefer a social, amenity-rich scene or a private retreat.
Ownership costs, rules, and rentals
HOA structures and private clubs
In Wailea, condominium HOAs often include common area maintenance, landscaping, pools, security, and exterior upkeep, plus utilities for shared spaces. Dues can be substantial in high-amenity complexes. Review reserve studies, special assessment history, insurance deductibles, pet and guest policies, and minutes from recent meetings.
In Makena, many single-family estates have minimal or no traditional HOA, yet gated communities and private clubs may have dues, initiation fees, and assessments. Private road maintenance or shared infrastructure can add recurring costs. For properties tied to clubs, read membership agreements closely for transferability, guest rules, and assessment schedules.
Short-term rental rules and taxes
Maui County regulates vacation rentals. Zoning, permits, and enforcement can shape both your ability to rent and your net income. Start with the Maui County Planning Department to understand current ordinances and permitting. If you plan to rent, you must also comply with Hawaii’s transient accommodations taxes. The Hawaii Department of Taxation provides guidance on TAT requirements and related filings. Wailea’s resort condos typically have stronger short-term rental demand and management infrastructure. In Makena, rental potential depends on property type, HOA rules, and any club restrictions.
Insurance and coastal exposure
Both Wailea and Makena include oceanfront or near-ocean properties where premiums for wind, hurricane, flood, and coastal risks can be higher. Insurance markets can shift quickly. Get quotes early and verify coverage for flood, storm surge, tsunami, and mold, along with deductibles. For site-specific risk review, consult the FEMA Flood Map Service Center and the NOAA Sea Level Rise Viewer.
Risks and long-term considerations
Coastal hazards and sea-level rise
Shoreline parcels may face erosion, stricter setback rules, and limits on seawall construction. Evaluate elevation, distance to Mean Higher High Water, erosion history, and any county or state sea-level rise projections affecting construction or future insurance costs. Factor these into your long-term maintenance and exit planning.
Infrastructure and emergency planning
South Maui relies on a limited number of primary roads and can experience seasonal traffic. In an emergency, access routes, evacuation plans, and response times matter. Confirm whether roads are county maintained or private, and clarify responsibilities for any private infrastructure.
Resale and marketability
Turnkey Wailea condos that allow short-term rentals are often easier to market to second-home buyers and investors. Makena estates appeal to a more niche audience, which can extend time to sell for unique or trophy properties. Keep an eye on Maui luxury demand, seasonal patterns, and inventory tightness. For a current snapshot, review the Realtors Association of Maui’s market reports.
Cultural and regulatory sensitivities
Coastal projects can involve cultural and environmental considerations, especially near shoreline access, archaeological sites, or sensitive habitats. If you plan future improvements, expect rigorous review and engage experts early.
Quick lifestyle snapshots
A Wailea weekend
You wake up in a resort condo, stroll the coastal path, and settle into a protected beach with easy access and services. Friends play a morning round at Wailea Golf Club while your guests book a spa treatment. Dinner is a short stroll or quick drive away. If you rent when you are off island, your manager handles turnover and guest services.
A Makena retreat
You step onto a wide lanai with a panoramic ocean view and almost no rooftops in sight. Your day centers around privacy, a quiet stretch of shoreline, and time with family. Groceries, dining, and golf are a short drive away, and the home is primarily for your personal use. You trade walkable amenities for a secluded, estate-scale setting.
When to choose Wailea vs. Makena
Choose Wailea if you want:
- Turnkey condo living with strong rental demand.
- Walkable access to beaches, dining, and golf.
- Robust property management and guest services.
- Faster liquidity potential within the resort condo segment.
Choose Makena if you want:
- Maximum privacy on larger oceanfront or near-ocean parcels.
- Estate-style living with fewer immediate neighbors.
- A personal retreat you will occupy more than you rent.
- Big natural landscapes and uninterrupted coastal vistas.
Buyer due-diligence checklist
Use this checklist to compare properties in Wailea and Makena. Request documents early and build a clear plan for ownership and management.
Lifestyle and use
- Define primary use: sole owner occupation, frequent visits, dedicated rental program, or mixed use.
- Anticipated frequency of visits and need for turnkey management vs self-management.
Site and property condition
- Comprehensive home inspection, including roof, foundations, seawalls, and drainage.
- Coastal hazards review: elevation relative to Mean Higher High Water, erosion history, FEMA flood zone, and county or state sea-level rise projections.
- Review permit history and any unpermitted work.
Financials and taxes
- Current property tax assessment and historical trend, plus any deferred taxes or liens.
- Obtain insurance quotes for wind, flood, liability, and umbrella coverage.
- Run pro forma for rental scenarios, including transient accommodations taxes and estimated management fees.
HOA, CC&R, and club agreements
- Review CC&Rs, bylaws, reserve study, recent meeting minutes, budgets, and any pending litigation.
- Confirm rental rules, guest policies, parking rules, and special assessment history.
- For private clubs, review membership agreements, initiation fees, transfer rules, guest access, and clubhouse assessment schedules.
Marketability and comps
- Obtain recent comparable sales and days-on-market data for a like-property.
- Check inventory levels in both Wailea and Makena for your target segment.
Utilities, services, and management
- Confirm utilities availability, including sewer vs septic, water source, and capacity constraints.
- Vet local property management, housekeeping, and onsite maintenance options.
Legal and title matters
- Order a title search for easements, access rights, public rights-of-way, and any conservation or historic restrictions.
- Confirm boundaries with a current survey, especially if waterfront proximity is critical.
Environmental and cultural reviews
- Check for protected species habitat, archaeological sites, or environmental restrictions that could limit future construction or shoreline stabilization.
Exit strategy
- Estimate annual holding costs and a realistic sale timeline under current market conditions.
- Decide whether you need immediate cash flow or prioritize long-term appreciation and private use.
The bottom line
Wailea and Makena both deliver extraordinary South Maui living. Your best fit comes down to whether you value resort convenience and rental optionality or ultimate privacy and estate presence. Before you act, confirm current MLS comps, HOA and club documents, insurance quotes, and coastal risk data. When you are ready to explore, connect with a local expert who can curate options, arrange discreet tours, and guide you through ownership details from first look to closing. For a confidential consultation tailored to your goals, contact Riette Jenkins.
FAQs
What is the main difference between Wailea and Makena for second homes?
- Wailea prioritizes resort convenience and condo living, while Makena focuses on lower-density privacy, larger parcels, and estate properties.
Can I offer short-term rentals in Wailea or Makena?
- It depends on zoning, permits, and HOA or club rules. Start with the Maui County Planning Department and review property-specific HOA documents before assuming rental eligibility.
How do transient accommodation taxes affect my rental income?
- If you rent, you must collect and remit Hawaii transient accommodations taxes. See the Hawaii Department of Taxation TAT guidance and consult your tax professional.
Is beach access different between the two areas?
- Wailea has multiple protected beaches with easier access and amenities. Makena’s Big Beach is expansive and more rugged, with fewer facilities and a stronger shorebreak. Review conditions via Makena State Park resources.
Are insurance costs higher for oceanfront properties in South Maui?
- Coastal homes can carry higher premiums for wind, hurricane, and flood risks. Get quotes early and check site exposure using the FEMA Flood Map Service Center and NOAA Sea Level Rise Viewer.
