Ho‘olei at Grand Wailea Condos in Wailea Maui
If you want “villa living” in the heart of Wailea—space, privacy, a garage, and resort-style amenities—Ho‘olei at Grand Wailea is one of Maui’s most sought-after luxury condo communities. Set in a gated enclave just across the street from the Grand Wailea Resort, Ho‘olei offers the feel of a high-end townhome neighborhood with the convenience of being short walking distance from Wailea Beach, The Shops at Wailea, and Wailea’s world-class dining, golf, tennis, and world classs spa’s.
Below is active list of Hoolei villa units for sale
Below is a overview: how many units are in Ho‘olei, what the floor plans look like, the amenities owners love, the connection to the Grand Wailea, and what today’s market environment means if you’re thinking about buying or selling.
How many units are in Ho‘olei?
Ho‘olei is made up of 120 luxury villa-style residences in Wailea. Hawaii Life This limited unit count is one reason the community tends to hold long-term appeal—there simply aren’t many properties on Maui that combine this much interior space with this level of resort adjacency.
Type of units and floor plans
Ho‘olei residences are two-story townhome-style villas designed for privacy, indoor-outdoor living, and the flexibility to use the property as a primary residence, second home, or (where applicable) a high-end short-term rental.
Most residences are built around three primary floor plans (commonly referenced as Plumeria, Maile, and Hibiscus), with layouts designed so each villa lives independently—often described as having a garden entry feel, generous lanais, and a private elevator in many configurations.
In terms of scale, Ho‘olei is known for offering true “home-sized” interiors. Published community guidance notes three floor plans ranging roughly from 2,400 to 3,076 square feet of living space. Hawaii Life
Across the community, the “signature” features buyers consistently look for include:
Spacious great rooms that open to large lanais (ideal for sunset dining and entertaining)
Chef-oriented kitchens and upscale finishes (varying by renovation level and year)
Attached garages (a big advantage in Wailea condo living)
A townhome layout that provides separation between living areas and bedrooms
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On-site amenities at Ho‘olei
Ho‘olei’s private amenities are a major part of the lifestyle—and they’re designed to feel like a resort without being crowded.
Owners and guests enjoy a tropical-style pool complex with:
Sandy beach entry pool
Dramatic waterfall and swim-in grotto
Two whirlpool spas
Children’s pool
Covered pavilion and outdoor entertaining/barbecue areas
There’s also a fitness facility with cardio and weight training equipment, plus men’s and women’s saunas, locker rooms, and showers.
And because you’re in Wailea, you’re minutes from Wailea’s golf and recreation network (Wailea golf courses, ocean activities, beach paths, and the Shops).
The Grand Wailea connection and Kūlana Club benefits
One of Ho‘olei’s most compelling advantages is the proximity to—and relationship with—the Grand Wailea, A Waldorf Astoria Resort. Grand Wailea describes Ho‘olei as a gated villa community across the street from the resort, providing a more residential experience while still connecting owners/guests to resort conveniences.
For many owners, the key word is Kūlana Club.
Kūlana Club is a membership program associated with Grand Wailea that can include privileges such as:
Complimentary access to Grand Wailea pools
Discounts on select resort experiences (food & beverage, luau, retail, beach amenities, and room rates, per the program’s terms)
Ho‘olei-focused guidance also notes that access to Grand Wailea’s grounds and spa is included with Kūlana Club membership (details and eligibility can vary, so it’s something we confirm during due diligence).
Kūlana Club Membership Benefits
- 30% off Grand Wailea’s Flexible Rate*
- 20% off Ho‘olei Villas at Grand Wailea Flexible Rate*
- 15% off Flexible Rates for Friends & Family*
- Daily Guest Passes for Friends & Family*
- 25% off Grand Wailea Food & Beverage Outlets**
- 20% off the Grand Lūʻau*
- 20% off Grand Wailea Retail Stores
- Complimentary Access to the Grand Wailea Pools
- 20% off Beach Chaise Loungers and Umbrellas*
- 10 Complimentary Beach Chaise Loungers & Umbrellas Set-Ups on a First Come, First Serve Basis* (1 set-up per Kūlana Club Membership)
- 10% off Grand Wailea Standard Cabanas & Casabellas*
- 10% off Grand Wailea Privately Catered Event Food & Beverage (with contract, on published menus only)
*Based on availability. Restrictions may apply.
**Please note member discounts do not apply to Nobu.
In practical terms, this is why Ho‘olei appeals to both second-home buyers and luxury vacationers: you can enjoy the privacy of a gated villa community, then be at Wailea Beach and the Grand Wailea experience in minutes.
Location: where Ho‘olei sits in Wailea
Ho‘olei is positioned in the core of Wailea—near Wailea Beach, The Shops at Wailea, and Wailea’s resort corridor. You’re close to the Wailea Blue golf course area, and just a short drive to Makena’s beaches and coastline. Ho‘olei’s “up the hill” setting is also why many villas capture ocean views while avoiding the foot traffic you see directly along the beachfront path.
SOLD HOOLEI VILLA UNITS
Current market: what’s happening now (and what it means for Ho‘olei sellers)
Maui’s condo market has been in a rebalancing phase: more inventory, longer days on market, and buyers who are more selective—especially about condition, HOA costs, and short-term rental considerations. One recent Maui market update noted condo median pricing softening and days on market rising, with added uncertainty tied to short-term rental regulation discussions. Maui Real Estate+1
Wailea/Makena tends to behave as its own luxury micro-market, often with fewer sales but premium pricing relative to the island-wide condo median.
So what does that mean specifically for Ho‘olei?
Turnkey wins. Updated, well-staged villas tend to stand out when buyers have choices.
Pricing strategy matters more than ever. In a slower market, the first 2–4 weeks are critical for momentum.
Marketing reach is everything. Ho‘olei attracts a mix of Hawaii buyers, mainland second-home buyers, and buyers comparing Wailea condos against single-family options—so your exposure needs to be broad, polished, and persistent.
Why list your Ho‘olei condo with Steven Nickens and Hawaii Life Real Estate Brokers
Ho‘olei is not a “generic condo listing.” Buyers compare floor plans, building positions, view corridors, privacy, upgrades, elevator/garage functionality, and the details around resort-access programs. You want representation that can translate all that into a clean strategy—and defend value during negotiation.
When you list with Steven Nickens and Hawaii Life Real Estate Brokers, you’re getting:
Deep Wailea expertise: knowing how Ho‘olei compares to Wailea Beach Villas, Wailea Point, and other luxury Wailea options—and how buyers shop across them
A clear pricing and presentation plan: staging guidance, renovation ROI priorities (where needed), and positioning that targets the most qualified buyer pool
High-impact marketing: premium photography/video, strong online distribution, and direct outreach to active Wailea/Makena buyers already in the pipeline
Experience that protects your bottom line: from offer structure to appraisal/inspection strategy to keeping escrow on track
- Steve has worked on sales teams at Hoolei, Wailea Beach Villas, Papali Wailea with The Wailea Group, and Wailea Fairway Villas.
Thinking about selling in Ho‘olei?
If you’d like a current value opinion on your Ho‘olei villa—based on the most recent closed sales, active competition, upgrades, view, and location within the community—reach out to Steven Nickens with Hawaii Life Real Estate Brokers. I’ll help you understand where your property fits in today’s Wailea luxury market and what it would take to sell with confidence and strong results. What’s Your Property Worth?
Comparative Market Analysis (CMA) 2024-2025
Prepared by: Steven Nickens, Hawaii Life Real Estate Brokers
Subject Property Overview
• Living Area: 2,619 sq ft
• Bedrooms/Baths: 3 BD | 3.5 BA
• Style: Luxury townhouse condominium
• Location: Mid-row
• Views: Good mid-row ocean views
• Tenure: Fee Simple
• Year Built: 2008
Unit | SF | Sold Price | $/SF | Notes | |
A-1 – 52 Ho‘olei Cir | 3,076 | $6,500,000 | 23 | Top row, great views | |
M-4 – 17 Makakehau | 2,619 | $5,850,000 | 41 | Same size | |
L-4 – 69 Makaehau | — | $5,750,000 | 99 | Nice views | |
L-3 – 23 Makaehau | — | $6,100,000 | — | Strong views | |
2024 Closed Sales (Peak Market)
DOM $2,114 $2,234 — — 2025 Closed Sales (Market Reset)
Original $5,995,000 $5,395,000 Market Value Opinion – Unit P-3
Estimated Market Value (Today): $4,900,000 – $5,100,000
Recommended List Price: $4,995,000
Expected Sale Range: $4,850,000 – $5,050,000
Pricing reflects 2025 buyer behavior, mid-row positioning, and size-matched Ho‘olei sales.
Unit | SF | Sold Price | $/SF | DOM | |
J-2 – 57 Makakehau | 2,426 | $4,150,000 | $1,711 | 364 | |
N-4 – 15 Kiloa St | 2,619 | $4,800,000 | $1,834 | 222 | |
If you have questions about buying or selling in Hoolei, give me a call.
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