Thinking about a Maui second home but torn between Wailea and Makena? You’re not alone. Both sit along South Maui’s stunning coastline and offer world-class beaches, but they feel very different day to day. In this guide, you’ll get a clear, side-by-side look at lifestyle, convenience, property types, beach access, rental and ownership rules, plus a practical checklist and self-assessment quiz to help you pick the best fit. Let’s dive in.
Wailea vs. Makena at a glance
Wailea and Makena are neighboring areas in South Maui, about a 30 to 45 minute drive from Kahului Airport depending on traffic and your exact address. Wailea sits immediately north of Makena. You’ll find more hotels, dining, and shopping in Wailea, while Makena stretches further south along a quieter, more natural coastline.
- Wailea: Planned resort-residential community with manicured grounds, golf courses, and clusters of shops and restaurants. Larger mix of turn-key condos and resort residences.
- Makena: Low-density, coastal setting with larger parcels and estate properties, fewer commercial centers, and dramatic shoreline anchored by Makena State Park.
Lifestyle and vibe
Wailea vibe
Wailea blends resort energy with residential comfort. Expect manicured landscaping, multiple public beach access points, and a higher daytime population due to nearby hotels and visitors. If you value walkability within resort areas and easy access to services, Wailea delivers.
Makena vibe
Makena offers a quieter, nature-forward atmosphere with fewer on-site services. Makena State Park draws day visitors to Big Beach and Little Beach, yet the residential fabric feels private and low-key. You’ll drive to Wailea or Kihei for many errands, which is a tradeoff for added seclusion.
Amenities and daily convenience
- Shopping and dining: Wailea places you close to restaurants and boutique shopping within short drives or walks from many resort clusters. In Makena, you’ll head 5 to 15 minutes toward Wailea or Kihei for most errands.
- Groceries and medical: Everyday services and medical providers are more accessible from Wailea. Makena residents typically plan errands in batches.
- Transportation: Both areas are car-dependent outside resort hubs. In condos, review guest parking rules and any county permitting requirements. For single-family properties, confirm driveway capacity and street parking policies.
Property types and inventory
Wailea homes and condos
Wailea features a wide range of condominium communities, from 1980s–1990s buildings to newer luxury residences. You’ll also find single-family homes and townhomes, but condos are more prevalent. If you want a ready-to-enjoy second home with resort amenities, Wailea often offers more options that fit that brief.
Makena homes and condos
Makena skews toward single-family estates on larger lots, many built as custom homes for owner occupancy. Condo options exist but are fewer and often limited to smaller or luxury developments with fewer total units. Inventory suitable for short-term vacation rental may be more limited here, and HOAs can be more restrictive.
Beach access and coastal realities
- Public beaches: Wailea’s coastline includes several public beaches with established access points and walkable beach paths. Makena State Park is a major attraction with broad sandy stretches and rugged shoreline areas.
- Coastal hazards: Wherever you buy along the coast, verify FEMA flood zones, tsunami evacuation status, historic shoreline setbacks, and any Special Management Area or Conservation District constraints with Maui County and the State of Hawai‘i. Sea-level rise, erosion, and coastal storms can influence permitting, insurance, and future maintenance plans.
- Everyday impacts: Being close to popular beaches can raise visitor traffic, parking pressure, and noise. If you plan to host guests or consider short-term rentals, proximity to resort beaches can make access easier and more marketable. If you prioritize privacy, look for properties with buffered access.
Rentals, taxes, and ownership costs
Short-term rentals
Maui County enforces short-term rental regulations and permits. Rules and enforcement evolve, so confirm current permit status for any property you consider. Many Wailea condos participate in resort or third-party management programs and have specific HOA rental rules. Makena HOAs, where applicable, may be more restrictive or not structured for nightly rentals. If you intend to rent, verify Transient Accommodations Tax and General Excise Tax obligations and ensure the property is properly licensed.
Taxes, insurance, and utilities
- Property tax: Both areas follow Maui County tax rules. Classification and exemptions affect your annual bill, so review the parcel’s current status and rates.
- Insurance: Coastal properties often carry higher premiums for wind or hurricane coverage, and flood insurance may be required in FEMA flood zones. Start quotes early and ask about coverage exclusions related to salt air and mold.
- Utilities: Confirm sewer versus septic or cesspool status. Some older rural parcels still use non-sewer systems, and Hawaii has programs related to cesspool upgrades. Always confirm water and electrical capacity if you plan to remodel or add structures.
- HOAs and maintenance: Wailea condos typically have higher HOA fees that cover resort amenities and common-area care. Makena single-family homes may have lower or no HOA fees but higher ongoing maintenance for landscaping, pools, and private roads.
Resale, liquidity, and marketability
- Wailea: Condos in active resort areas tend to attract steady demand from second-home buyers and investors who value turn-key living and amenities. Changes to HOA or county rental rules can affect investor demand, so keep policy trends on your radar.
- Makena: Large estates appeal to a more specialized buyer pool seeking privacy, land, and coastline access. Resale can take longer and depends heavily on the property’s unique value, such as views, lot size, and shoreline characteristics. Comparable sales may be fewer, which can affect pricing strategy.
Practical due diligence checklist
Use this list to evaluate any Wailea or Makena property, especially if you’re off island.
- Confirm current zoning and allowable uses with Maui County Planning.
- Verify short-term rental permit status, including grandfathering if applicable, with County records and HOA documentation.
- Request HOA documents: CC&Rs, budgets and reserve studies, recent special assessments, rental restrictions, and guest parking rules.
- Pull FEMA Flood Zone and tsunami evacuation maps and review shoreline setbacks with State and County files.
- Confirm sewer versus septic or cesspool status and check Hawaii Department of Health guidance on upgrades.
- Obtain early insurance quotes for homeowner, wind/hurricane, and flood coverage, and ask about exclusions for mold and salt air.
- Review Maui County Real Property Tax classification, assessed value, and current annual tax expense.
- Request historical utility bills, maintenance records, and permits for major work from the seller or property manager.
- For condos: review rental income history, occupancy, and rental restrictions. For homes: confirm guest parking capacity and neighborhood rental policies.
- Map drive times to airport, grocery, medical services, and identify evacuation routes.
Self-assessment quiz: Which area fits you?
Score each answer 1–3 points. Higher scores lean Wailea; lower scores lean Makena.
- Preferred daily vibe?
- Resort amenities, restaurants, walkability (3)
- Moderate services, drive for most errands (2)
- Secluded, nature-focused, minimal services (1)
- Housing type you prefer?
- Turn-key condo or resort residence (3)
- Townhome or smaller single-family (2)
- Large estate, custom single-family (1)
- Importance of on-site guest infrastructure?
- Very important: front desk, management, pools, golf (3)
- Somewhat important (2)
- Not important (1)
- Will you rely on short-term rentals for income?
- Yes, essential for the plan. Verify current permitting (3)
- Maybe some rentals (2)
- No, primarily private use or long-term rental (1)
- Tolerance for visitor traffic near beaches?
- Comfortable with higher day-use areas and tourist traffic (3)
- Moderate tolerance (2)
- Prefer minimal crowds (1)
- Desire for privacy and land area?
- Low, happy with smaller footprint and shared amenities (3)
- Moderate (2)
- High, want space and seclusion (1)
- Maintenance and management preference?
- Prefer low-maintenance, professionally managed property (3)
- Will hire a manager or coordinate remotely (2)
- Hands-on with local caretakers for a larger property (1)
Score guide
- Mostly 3s: Wailea likely fits better. You value resort amenities, walkability, and turn-key options.
- Mixed 2s and 3s: Explore the Wailea–Makena boundary, smaller Makena condos, or Wailea single-family pockets.
- Mostly 1s: Makena likely fits better. You want privacy, land, and a nature-forward setting.
Next steps
- Book a local consultation to build a focused short list.
- Ask about current STR permitting and HOA rules for each candidate property.
- Plan a scouting trip with daytime and evening visits in both areas on weekdays and weekends.
How to choose with confidence
Finding the right fit comes down to tradeoffs. Wailea offers convenience and a broad condo selection with resort infrastructure. Makena offers privacy, land, and a quieter coastline. Your best decision blends lifestyle, ownership goals, and a clear understanding of regulations, costs, and long-term risks along the shore.
If you want a trusted local partner to narrow the field, coordinate vendors, and guide you through off-island logistics, reach out to Steve Landin. You’ll get attentive, detail-first representation and a community-minded approach on every transaction.
FAQs
What’s the main difference between Wailea and Makena lifestyles?
- Wailea emphasizes resort-style living with more amenities and walkability within resort areas, while Makena offers a quieter, low-density coastal setting with fewer on-site services.
How close are Wailea and Makena to Kahului Airport for second-home owners?
- Typical drive time is about 30 to 45 minutes depending on traffic and the specific property location.
Are short-term rentals allowed in Wailea and Makena condos and homes?
- It depends on county permits and HOA rules; verify current licensing, any grandfathering, and tax obligations before you buy.
What coastal risks should I evaluate before buying near the shoreline?
- Review FEMA flood zones, tsunami evacuation maps, shoreline setbacks, and Special Management Area rules, and understand how erosion and storms can affect insurance and permitting.
Which area is better for turn-key second homes with amenities?
- Wailea typically offers a larger inventory of turn-key condos and resort residences with on-site amenities that suit second-home buyers.
Which area suits buyers seeking privacy and larger land?
- Makena tends to provide larger single-family lots and estate properties with a more secluded, nature-focused setting.
