MAUIRESORTGUIDE.COM
Find your perfect Maui resort — from someone who actually lives here
Local Knowledge with 20 years on Maui. Experienced Hawaii Real Estate Broker & Investor with an Architecture Degree.
Jesse’s picks
Where I'd send my clients
Wailea / Makena
4 PROPERTIES
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Wailea
Four Seasons Maui
The gold standard of luxury on Maui — AAA Five Diamond rated with impeccable service, a pristine beachfront setting, and the kind of attention to detail that justifies every dollar. If you’re going to splurge anywhere on the island, this is the place.
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Makena
Makena Surf
Tucked away on the quieter south side of Maui, Makena Surf offers spacious beachfront condos with a level of privacy that the busier resorts simply can’t match. Come here when you genuinely want to disconnect.
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Wailea
Wailea Beach Villas
Arguably the best-positioned condo property in Wailea — walking distance to the Shops at Wailea, multiple restaurants, and some of the island’s most beautiful beaches. Luxury condo living in the heart of the action.
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Kihei
Mana Kai Maui
The gold standard of luxury on Maui — AAA Five Diamond rated with impeccable service, a pristine beachfront setting, and the kind of attention to detail that justifies every dollar. If you’re going to splurge anywhere on the island, this is the place.
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Wailea
Four Seasons Maui
The gold standard of luxury on Maui — AAA Five Diamond rated with impeccable service, a pristine beachfront setting, and..
Aerial
Makena
Makena Surf
Tucked away on the quieter south side of Maui, Makena Surf offers spacious beachfront condos with a level of privacy..
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Wailea
Wailea Beach Villas
Arguably the best-positioned condo property in Wailea — walking distance to the Shops at Wailea, multiple restaurants..
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Makena
Makena Surf
Tucked away on the quieter south side of Maui, Makena Surf offers spacious beachfront condos with a level of privacy..
Ka'anapali
4 PROPERTIES
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Ka’anapali
Honua Kai
The best condo resort on the island for families — full kitchens, multiple pools, direct beach access, and enough space for everyone to spread out. Duke’s Beach House right on property seals the deal.
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Ka’anapali
The Whaler
Sitting right on Ka’anapali Beach with Whalers Village shopping and dining steps from your door, The Whaler is hard to beat for convenience and value. A classic Maui condo property that delivers every time.
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Ka’anapali
Ka'anapali Ali'i
One of the most spacious and refined condo properties on Ka’anapali Beach — oversized units, premium finishes, and a quieter atmosphere than the big hotel resorts nearby. Ideal for longer stays.
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Ka’anapali
Sheraton Maui
Perched on the iconic Black Rock point at the north end of Ka’anapali Beach, the Sheraton delivers a full resort experience at a more accessible price point. The cliff diving ceremony at sunset is unforgettable.
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Ka’anapali
Honua Kai
The best condo resort on the island for families — full kitchens, multiple pools, direct beach access, and enough space fo..
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Ka’anapali
The Whaler
Sitting right on Ka’anapali Beach with Whalers Village shopping and dining steps from your door, The Whaler is hard to be..
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Ka’anapali
Ka'anapali Ali'i
One of the most spacious and refined condo properties on Ka’anapali Beach — oversized units, premium finishes, and a..
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Ka’anapali
Sheraton Maui
Perched on the iconic Black Rock point at the north end of Ka’anapali Beach, the Sheraton delivers a full resort experience..
Kapalua
2 PROPERTIES
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Kapalua
Montage Kapalua Bay
Nestled above the calm waters of Kapalua Bay, the Montage delivers an intimate, ultra-refined experience with oversized residences and personalized service that rivals anything on the island. This is Maui at its most exclusive.
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Kapalua
Ritz-Carlton Kapalua
Set on a dramatic bluff above two championship golf courses, the Ritz-Carlton Kapalua is the definitive choice for golfers and spa enthusiasts. The cooler elevation and lush surroundings make it feel like a completely different Maui.
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Kapalua
Montage Kapalua Bay
Nestled above the calm waters of Kapalua Bay, the Montage delivers an intimate, ultra-refined experience with oversized
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Kapalua
Ritz-Carlton Kapalua
Set on a dramatic bluff above two championship golf courses, the Ritz-Carlton Kapalua is the definitive choice fo..
Unique Experiences
2 PROPERTIES
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Hana
Travaasa Hana
The most remote and soul-restoring property on Maui — a wellness-focused retreat at the end of the Road to Hana where the jungle meets the ocean and your phone signal disappears. Stay at least two nights or you’ll wish you had.
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Lahaina
Lahaina Shores
A charming boutique beachfront property steps from the historic heart of Lahaina town — one of the few places where you can walk to Front Street dining and still wake up to ocean views. Understated and genuinely local in feel.
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Kapalua
Travaasa Hana
The most remote and soul-restoring property on Maui — a wellness-focused retreat at the end of the Road to Hana..
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Lahaina
Lahaina Shores
A charming boutique beachfront property steps from the historic heart of Lahaina town — one of the few places where you..
jw
Jesse G. Wald
Maui-based real estate broker · 20 years local · Licensed drone pilot · Top 1% nationally · Architecture degree · 76K YouTube subscribers · 58K Instagram followers
Quick answers
Where I'd send my clients
Wailea vs Ka'anapali — which is better?
Wailea for pure luxury and calm. Ka’anapali for more energy, dining, and nightlife. Both have world-class beaches.
When is the best time to visit Maui?
April–May and September–October hit the sweet spot — great weather, smaller crowds, better rates than peak winter.
Hotel or vacation rental?
Hotel for a true resort experience with amenities. Vacation rental if you want a kitchen, more space, or a local neighborhood feel.
Is Hana worth the drive?
Absolutely — but stay at least one night. The Road to Hana is best experienced without rushing back. Travaasa Hana is worth every penny.