Luxury rentals in Wailea

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Top-rated luxury holiday rentals in Wailea

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Luxe

Flat in Wailea

4.94 out of 5 average rating, 18 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

The open living area features a spacious sectional sofa, a glass coffee table, and a decorative rug. Large sliding doors lead to an outdoor space framed by tropical greenery, allowing natural light to fill the room. The kitchen area with wooden cabinetry and modern appliances is visible in the background.

Flat in Wailea

4.67 out of 5 average rating, 6 reviews

Wailea Hoolei 93-3 Luxe Villa w/ Pool & Lanai

The Stice Team — Powered by Gather Vacations. Maui Born and Raised Professionals. Your Local Experts in Crafting Unforgettable Stays. Welcome to Ho‘olei 93-3, a lavish 3-bedroom, 3.5-bath villa nestled in the private, gated enclave of Ho‘olei, just a short stroll from world-famous Wailea Beach and the iconic Grand Wailea Resort.

Luxe

The open-concept living area features a spacious sectional sofa and a modern kitchen island with bar seating. Large glass doors allow for a seamless transition to the outdoor lanai, showcasing panoramic ocean views in the distance.

Apartment in Wailea

5 out of 5 average rating, 10 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.

Luxe