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Wailea and Makena Real Estate: Luxury Homes, Villas and 2026 Rules

By Tony Kawaguchi, REALTOR (RS-66616), The Kawaguchi Group, eXp Realty (RB-21841). Selling in Hawaii since 2005. Updated November 13, 2026.

Aerial view of the Wailea resort coastline and beaches
The Wailea coast from the air, March 2018. Photo: Forest and Kim Starr, CC BY 3.0 US, via Wikimedia Commons.

Quick answer (updated November 13, 2026): Wailea and Makena are South Maui's luxury market. October 2026 median prices (Title Guaranty Hawaii market report) show 7 house sales at a $2.9 million median and 10 condo sales at a $3.3 million median, with Wailea among the island's most active neighborhoods. Before you buy, confirm the property's zoning and association rules on rentals, look at shoreline and SMA status, and run taxes in the upper tiers, where Maui's non-owner-occupied rate reaches $17.00 per $1,000.

Wailea is a master-planned resort community south of Kihei, built around golf courses, a beach walk, hotels and a shopping village. Makena, farther south, is quieter, with a former resort area, large view lots, and open lava coast toward the state reserve land at the end of the road.

For buyers this is mostly a market of resort villas and condos, luxury single-family homes and custom homesites, and the details of each project matter more than the area median.

Villas, condos and homes

Wailea condos and villas range from golf-course projects to oceanfront communities, many with their own amenities, on-site management and high association dues. Grand Champions was among the Maui complexes with a sale in October. Single-family homes sit in gated and non-gated neighborhoods on the slopes above the resort, and Makena offers some of the island's larger view lots and custom homes. Homesites and new construction move through design review with the master association before county permits.

Wailea/Makena house median, Oct 2026$2.9 million (7 sales)
Wailea/Makena condo median, Oct 2026$3.3 million (10 sales)
Maui County house median, Oct 2026$1,179,000

These are October 2026 median prices from the Title Guaranty Hawaii market report for Maui (effective November 2, 2026). Title Guaranty is a Hawaii title and escrow company, and its free monthly report compiles the island board's MLS sales statistics. One month is a small sample, so treat any single-area median as a starting point and look at actual comparable sales.

Golf course and coastline at Wailea seen from the air
Golf course and shoreline at Wailea, March 2018. Photo: Forest and Kim Starr, CC BY 3.0 US, via Wikimedia Commons.

Rental rules

Apartment-zoned condos: Maui County's Ordinance 5909 (Bill 9) phases out transient vacation rental use in the A-1 and A-2 apartment districts. In the West Maui community plan area the use must end on January 1, 2029; everywhere else in the county it ends on January 1, 2031. Validly existing timeshare units and uses operating under a variance are exempt, and hotel-zoned properties are not covered. A separate 2026 ordinance created new H-3 and H-4 hotel districts that some apartment-zoned complexes are trying to move into, one property at a time, so a building's status can change; I track it in my Maui rezoning update.

Houses: in residential and agricultural districts, nightly rentals generally need a county short-term rental home or bed-and-breakfast permit, and those permits are limited. Never assume a house can be rented nightly because a previous owner did it. In Wailea and Makena, some projects are hotel-zoned, some are apartment-zoned and face the January 1, 2031 deadline, and many associations set their own minimum-stay rules. Confirm all three before you count on rental income.

Nightly rental income is taxed separately from property tax: the state transient accommodations tax is 11% as of January 1, 2026, each county adds a 3% county TAT, and general excise tax is 4.5% in both Maui County and Hawaii County, so plan on about 18.5% of gross rent before income tax.

Hazards and insurance

Before you fall for a view, check four maps for the exact parcel: the state's Flood Hazard Assessment Tool for FEMA flood zones, the tsunami evacuation zone map, the Hawaii Sea Level Rise Viewer for shoreline exposure, and the Special Management Area boundary, which adds a permit layer for most work near the shoreline. After the August 2023 wildfires, I also ask about vegetation, defensible space and insurance availability early, especially on dry leeward slopes. Condo buyers should read the association's budget, reserve study and master insurance policy, because master premiums have pushed maintenance fees up across Hawaii.

Wailea and Makena are hot and dry, and brush fire is a real consideration on the open land above and beside the resort. Shoreline properties also face erosion and setback rules.

Aerial view of Wailea Point and nearby resort hotels
Wailea Point and nearby resorts, March 2018. Photo: Forest and Kim Starr, CC BY 3.0 US, via Wikimedia Commons.

Getting around

From Kahului Airport, Wailea is about 30 to 40 minutes and Makena about 35 to 45 minutes. Kihei shopping is 5 to 15 minutes away. These are our own estimates for light traffic, not official figures; rush hour, events and road work can add a lot of time.

Land tenure

Most Maui homes sell fee simple, meaning you own the land and the building. Leasehold still shows up, mainly in some condo projects, and when it does, the years left on the lease and the lease rent terms matter as much as the price, because they affect value and financing. Department of Hawaiian Home Lands homestead leases have their own eligibility rules and are not sold on the open market like fee simple homes. On older rural parcels, title can involve kuleana or access questions that a title company should clear before closing.

Property taxes on high-value homes

Maui County taxes by how a property is used, not just what it is worth, so the same house can carry very different bills. If you live in the home full time and qualify, the county's home exemption takes $300,000 off the assessed value and moves you into the low owner-occupied class. To qualify you must occupy the home more than 270 days a year, not rent out the whole property, and file a Hawaii resident income tax return with a Maui County address; the claim deadline for the 2027 assessment year is December 31, 2026.

Source: County of Maui Resolution No. 26-69, FD2. Tiers apply to the portion of value in each band.
Maui County class (FY July 1, 2026 - June 30, 2027) Rate per $1,000 of net taxable value
Owner-occupied (with home exemption) $1.65 up to $1.5M; $1.80 from $1.5M to $4.5M; $5.00 above $4.5M
Non-owner-occupied (second homes, most investor homes) $6.25 up to $1M; $9.00 from $1M to $2.5M; $17.00 above $2.5M
Long-term rental (12+ months to the same tenant, exemption granted) $2.90 up to $1.5M; $5.00 from $1.5M to $3M; $8.50 above $3M
TVR-STRH (permitted short-term rentals) $13.00 up to $900K; $15.00 from $900K to $3M; $17.00 above $3M
Hotel and resort / Time share / Apartment $11.80 / $14.90 / $3.50

Illustration only, before any minimum tax or other credits: on a home assessed at $3,000,000, the owner-occupied math starts by subtracting the $300,000 exemption from $3,000,000 and applying the tiered rates above, for about $4,635 a year. The same home as a second home in the non-owner-occupied class is roughly $28,250 a year. Check the county's assessment for the actual property.

A Wailea villa used as a permitted vacation rental is taxed in the TVR-STRH class, $13.00 per $1,000 up to $900,000, $15.00 to $3 million and $17.00 above.

Wailea and Makena real estate FAQ

How much does a home in Wailea cost?

The Title Guaranty Hawaii market report shows 7 Wailea and Makena house sales in October 2026 at a median of $2.9 million, and 10 condo sales at a median of $3.3 million. Individual prices vary widely by project and view.

Can I rent a Wailea condo nightly?

Only if the project's zoning and association rules allow it. Apartment-zoned units outside West Maui must end vacation rental use on January 1, 2031 under Ordinance 5909; hotel-zoned and timeshare properties are not covered.

What are property taxes on a Wailea home?

Using Maui County's July 2026 to June 2027 rates, a home assessed at $3,000,000 would be about $4,635 a year if you live there and get the $300,000 home exemption, or about $28,250 a year as a second home in the non-owner-occupied class, before any minimum tax or credits.

What is the difference between Wailea and Makena?

Wailea is the master-planned resort area with hotels, golf and a shopping village. Makena, to the south, is less developed, with larger lots, a former resort area and open coastline.

Do Wailea homes have association rules?

Most do. Expect a master association plus a project association, design review for remodels and new homes, and rules on rentals and use. Read them before you write an offer.

Is Wailea at risk from wildfire?

Wailea and Makena are dry, and brush fire is a consideration on the open land nearby. Ask about defensible space and get insurance quotes early.

How far is Wailea from Kahului Airport?

Our estimate is about 30 to 40 minutes in light traffic.

Can Tony help me buy in Wailea and Makena?

Yes. My team is based on Oahu, and for Maui purchases we help buyers through eXp Realty's statewide network, including referrals to agents who work Wailea and Makena every day. Call or text (808) 201-3577.

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Sources

Tony Kawaguchi, REALTOR (RS-66616), The Kawaguchi Group, eXp Realty (RB-21841). Selling in Hawaii since 2005. Phone (808) 201-3577. The Kawaguchi Group is based on Oahu; for neighbor-island purchases we work with buyers through eXp Realty's statewide network, including referrals to agents who work those areas every day. This page is general information, not legal, tax, insurance or financial advice. Market statistics are deemed reliable but not guaranteed and can be revised. Drive times are our own estimates for light traffic and will vary. Photos are of the general area and are not listings.

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