Luxury rentals in Wailea

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Top-rated luxury vacation rentals in Wailea

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Luxe

The outdoor area features a lap pool with lounge chairs arranged alongside. The villa's exterior is illuminated at dusk, showcasing elegant architectural details and large glass doors that provide views into the living spaces. A covered patio offers shaded seating for relaxation.

Villa in Lahaina

5 out of 5 average rating, 3 reviews

Blue Sky Villa

Blue Sky Villa in Maui has been designed and decorated to soothe your mind, body and soul. This magical villa brings you close to the setting of the ancient Hawaiian kings with architecture that swirls and soars in the manner of the ocean and sky before it. Within easy walking distance to Lahaina Town and a short drive to the beaches, Blue Sky Villa also offers a convenient location for exploring this spectacular island. This resplendent villa features one of the finest lap pools in all of Hawaii. Step into the soothing bubbles of the outdoor hot tub for a special treat. Indoors, you will find a media room, Wi-Fi access, ceiling fans and laundry facilities. Step onto the splendid balcony and ascend the open air winding stairs to your private meditation tower reminiscent of an ancient castle suffused on all directions by ocean and mountain vistas including Lanai, Kahoolawe, and the sublime peaks and contours of Pu’u Kukui. The grace and beauty of the outdoors at Blue Sky Villa are only matched by its pristine and vast interiors. This luxury house was built to enjoy the natural beauty and breezes of Maui, enabling the ultimate indoor/outdoor living experience. Doors fully retract in the master bedroom as well as the living and dining rooms. The living room features a white baby grand piano that awaits the life breath of music. This villa includes a premiere master bedroom where one feels as though they are floating on a cosmic ship of azure. The refined luxury of the master bathroom will take your breath away. There are four additional bedrooms with equal comfort and four additional bathrooms. This villa accommodates up to twelve guests. During your stay at Blue Sky Villa, you will be just a short drive away from Lahaina, Baby and Ka’anapali beaches. Both surfers and golfers will be in paradise as they explore their options in this iconic landscape. Nearby Lahaina is a heritage town transformed into a modern Maui hot spot. Lahaina offers a variety of unique art galleries, shops and restaurants. A historic 1800s whaling village, this area has been immortalized by Herman Melville in the classic Moby Dick. The delights of Maui await! Copyright © Luxury Retreats. All rights reserved. Permit #: STWM 2014/0002 HAWAII TAX ID #:051-843-4816-01 BEDROOM AND BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite open-air bathroom with rain shower and soaking bathtub, Dual vanity, Walk-in closet, Air conditioning, Lounge area, Television, Ceiling fan, Lanai, Outdoor furniture, Ocean view • Bedroom 2: King size bed, Shared access to bathroom with bedroom 3, Shower/bathtub combo, Air conditioning, Television, Ceiling fan • Bedroom 3: Queen size bed, Twin size bed, Shared access to bathroom with bedroom 2, Shower/bathtub combo, Air conditioning, Television, Ceiling fan • Bedroom 4: King size bed, Ensuite bathroom with shower/bath combo, Air conditioning, Television, Ceiling fan • Bedroom 5: Queen size bed, Ensuite bathroom with shower/bathtub combo, Air conditioning, Television, Ceiling fan, Balcony FEATURES AND AMENITIES • Private meditation tower OUTDOOR FEATURES • Lanai STAFF & SERVICES Extra cost (advance notice may be required): • Massage therapist • Activities and excursions • Mid-stay cleaning

Luxe

An aerial view showcases the ground-floor condo adjacent to idyllic Polo Beach, with the turquoise ocean stretching along the horizon. The sandy beach is framed by gently swaying palm trees, while the coastal path invites leisurely strolls. The shared pool can be seen amidst the lush greenery.

Apartment in Wailea-Makena

5 out of 5 average rating, 10 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.

Apartment in Kihei

5 out of 5 average rating, 3 reviews

Wailea Hoolei 93-3 Rarely Priced for Last Minute

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

A serene ocean scene features calm, clear waters reflecting a vibrant blue sky. Gentle waves lap against rocky shorelines adorned with green vegetation, creating a tranquil coastal atmosphere. Lush greenery in the foreground frames the expansive view of the Pacific Ocean, enhancing the sense of natural beauty.

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

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.

Condo in Kihei

5 out of 5 average rating, 5 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.