Luxury rentals in Hawaiian Islands

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Top-rated luxury holiday rentals in Hawaiian Islands

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Luxe

Villa in Kailua-Kona

4.96 out of 5 average rating, 76 reviews

Hale Ohia: Oceanfront Paradise

This is an exceptionally beautiful and unique oceanfront property in a secluded location near Kailua-Kona, offering pristine views of Holualoa Bay. Enjoy breathtaking ocean vistas, stunning sunsets, and a wide-open night sky in a luxurious, nature-immersed setting. The property includes three guest units and a main house, all thoughtfully built around a shared deck and showcasing fine craftsmanship with locally sourced Ohia wood. A true gem blending elegance, privacy, and natural beauty.

Luxe

Apartment in Wailea-Makena

5 out of 5 average rating, 14 reviews

Ocean Views | Polo Beach Club | Groundfloor Condo

Step straight onto the sand at Polo Beach—Wailea’s premier swimming beach—from this rare ground-floor condo with ocean views that will take your breath away. Located in the exclusive Polo Beach Club, this 2-bedroom retreat offers near-private beach access, a walkout lanai, and unbeatable proximity to Maui’s top coastal path. Inside, unwind with a chef’s kitchen, spa-style bathrooms, Moccamaster coffee, and Dyson Airwrap. This is five-star comfort, with the beach at your doorstep.

Luxe

Condo in Lahaina

5 out of 5 average rating, 7 reviews

Maui Resort Rentals: Honua Kai Hokulani 402

As one of Honua Kai's crown jewels. Hokulani 402 boasts an incredible 4th floor oceanfront vantage point in the closest column to the ocean at the entire Honua Kai Resort.. Treat your party to this "Ali'i" (Hawaiian word for royalty) residence with over 2200 sumptuous sq. ft. feet of interior space and some of Honua Kai's most spectacular oceanfront views. A Viking barbecue grill on the expansive 600 sq. ft. balcony completes the lavish experience.

Luxe

Villa in Kailua-Kona

5 out of 5 average rating, 10 reviews

Mele Kai Kona - Luxe Oceanfront Property with Pool

As close to the ocean as you can get, located in between two popular beaches in the heart of Kailua-Kona. The sundrenched interior is rich with coastal influence and a refreshing salted breeze. Beyond sky-high windows, the crystalline Kona Coast provides a striking vista. Pop open a bottle of icy champagne on the terrace as the sky transforms with an array of vivid hues. Copyright © Luxury Retreats. All rights reserved.

Luxe

Home in Koloa

5 out of 5 average rating, 4 reviews

Luxe Kauai Retreat | Pool • Spa • Ocean Views • AC

Magnificent, spectacular, and amazing describe Jasmine Villa, a brand-new 2024 Kukuiʻula retreat. This luxurious home offers sweeping views of the ocean, Kukuiʻula golf course, Hā‘upu mountains, sunrise, and full moonrise. Watch the Milky Way and meteor showers from the lanai, sun deck, or firepit. A perfect blend of comfort and natural beauty in one of Kauaʻi’s most exclusive communities.

Luxe

Home in Waikoloa Beach Resort

5 out of 5 average rating, 3 reviews

PiH: Nohea Kai ~Relax in Luxury, eBikes, Pool, Spa

Mauna Lani Resort -- Immerse yourself in the perfect fusion of island beauty and sophisticated luxury at this stunning 3-bedroom, 3,730-square-foot home. Nestled in the exclusive Nohea Community within Mauna Lani Resort, Nohea Kai offers an extraordinary sanctuary for up to 8 guests, providing the ultimate space to relax and unwind.

Luxe

Condo in Lahaina

4.67 out of 5 average rating, 3 reviews

KBM Resorts | FREE CAR Kapalua Bay KBV-34G4

Luxurious oceanfront villa with panoramic Molokai views, private lanai, gourmet kitchen, and spa-inspired master suite-perfect for a relaxing Maui escape with comfort, style, and island charm. Please note that this listing can accommodate up to 4 guests, with additional bedding provided via a sofa bed in the living room.

Luxe

Condo in Kihei

5 out of 5 average rating, 6 reviews

Wailea Hoolei 23-3 Your Ultimate Luxury 3Bedroom

The Stice Team — Powered by Gather Vacations. Maui Born and Raised Professionals. Your Local Experts in Crafting Unforgettable Stays. Welcome to Ho‘olei Residence 23-3 (L3), a show-stopping 3-bedroom, 3.5-bath villa set within Wailea’s coveted, gated Ho‘olei enclave on Maui’s sun-kissed south shore.