Wailea Luxury Vacation Rentals

These hand-selected stays feature elevated interior design and thoughtfully curated settings that meet discerning luxury expectations. Ideally located in premier beachfront areas, they place guests in the heart of Wailea with seamless access to resort amenities, dining, and beach experiences. 

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Treat yourself to an unforgettable retreat at Wailea Elua Village 1101, a stunning 1-bedroom, 1-bathroom ocean view condo nestled in the heart of Wailea, steps from Ulua Beach. This meticulously designed 1,025-square-foot vacation condo comfortably accommodates up to four guests, offering a perfect blend of luxury and comfort for your vacation geta
Wailea Elua Village 1101
1 Bedroom Ocean View Condo
Rating 5 (2)
1 bedrooms
1 baths
4 guests
Location Wailea, HI Icon of Ocean View Ocean View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
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Welcome to the Makena Surf E102 Beachfront Resort, your perfect oasis for a rejuvenating getaway. This stunning 2-bedroom, 2-bathroom oceanfront condo offers a luxurious escape for up to four guests. Step into the open-plan living area, where modern design meets comfort with a fully equipped kitchen, a cozy dining area, and a spacious living room w
Makena Surf E102 Beachfront Resort
2 Bedroom Oceanfront Condo - Platinum
Rating 5 (41)
2 bedrooms
2 baths
4 guests
Location Wailea, HI Icon of Oceanfront View Oceanfront View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
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Experience the very best in tropical island living from ocean view Wailea Beach Villas Penthouse 402. Revel in sweet sunsets and seasonal whale watching from your spacious, private lanai with scenic views of the Maui horizon, Molokini Crater and the island of Kaho'olawe. This beautiful two-bedroom, two-bathroom villa provides a delicate balance of
Wailea Beach Villas PH402
2 Bedroom Ocean View Condo - Platinum
Rating 5 (9)
2 bedrooms
2 baths
4 guests
Location Wailea, HI Icon of Ocean View Ocean View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
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Welcome to your serene oasis at Wailea Elua Village 107, a stunning 2-bedroom, 2-bathroom ocean view condo nestled in the heart of Wailea. This meticulously designed retreat offers a perfect blend of comfort and luxury, ideal for your next Hawaiian getaway.Step inside to find a spacious, open-concept living area adorned with modern furnishings and
Wailea Elua Village 107
2 Bedroom Ocean View Condo - Platinum
Rating 5 (7)
2 bedrooms
2 baths
4 guests
Location Wailea, HI Icon of Ocean View Ocean View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
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Wailea Beach Villas PH410 is a fourth floor penthouse suite that overlooks the central swimming pool with spectacular views of the Pacific Ocean and Wailea Beach, along with views of Kaho'olawe, Molokini and Lana'i.From your private elevator landing, the suite opens with a wide hallway leading past both bedrooms toward the great room where a genero
Wailea Beach Villas PH410
2 Bedroom Ocean View Condo - Platinum
Rating 5 (6)
2 bedrooms
2 baths
6 guests
Location Wailea, HI Icon of Ocean View Ocean View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
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Wailea Beach Villas Penthouse 404 is a stunning two-bedroom plus den, two-bathroom ocean view residence offering over 1,978 sq. ft. of elegant indoor-outdoor living. Situated on the fourth floor, this penthouse enjoys sweeping views of the Pacific Ocean, Kaho'olawe and Molokini, creating the perfect backdrop for your Maui vacation. The private lana
Wailea Beach Villas PH404
2 Bedroom Ocean View Condo - Platinum
Rating 5 (3)
2 bedrooms
2 baths
6 guests
Location Wailea, HI Icon of Ocean View Ocean View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
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CORALTREE RESIDENCE COLLECTION presents... Makena Surf G203Immerse yourself in tranquility at this secluded 2-bedroom, second-floor sanctuary overlooking Po'olenalena Beach. Tucked into one of the most private and quiet corners of the 32-acre botanical estate, this retreat provides elevated panoramic views of the Pacific—perfect for seasonal whale
Makena Surf G203 Beachfront Resort
2 Bedroom Oceanfront Condo - Platinum
Rating 5 (10)
2 bedrooms
2 baths
6 guests
Location Wailea, HI Icon of Oceanfront View Oceanfront View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
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Welcome to the Makena Surf A102 Beachfront Resort, your perfect oasis in Wailea, HI. This stunning 2-bedroom, 2-bathroom oceanfront condo sleeps up to six guests and offers a luxurious retreat with breathtaking views of the Pacific Ocean. Step inside to find a spacious, open-concept living area with a fully equipped kitchen, perfect for preparing m
Makena Surf A102 Beachfront Resort
2 Bedroom Oceanfront Condo - Diamond
Rating 5 (32)
2 bedrooms
2 baths
6 guests
Location Wailea, HI Icon of Oceanfront View Oceanfront View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
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Welcome to your serene oasis at Wailea Elua Village 706, a stunning 2-bedroom, 2-bathroom ocean view condo nestled in the heart of Wailea. This meticulously designed retreat offers a perfect blend of comfort and luxury, ideal for your next Hawaiian getaway.Step inside to discover a spacious, open-concept living area adorned with modern furnishings
Wailea Elua Village 706
2 Bedroom Ocean View Condo - Platinum
Rating 5 (2)
2 bedrooms
2 baths
4 guests
Location Wailea, HI Icon of Ocean View Ocean View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
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Welcome to the serene and luxurious Wailea Elua Village 2108, your perfect oceanside retreat. This stunning two-bedroom, two-bathroom condo offers a spacious 1,528 square feet of living space, comfortably accommodating up to six guests. The master bedroom features a king bed, while the second bedroom has a queen bed and a twin bed, ensuring a restf
Wailea Elua Village 2108
2 Bedroom Ocean View Condo - Diamond
Rating 5 (33)
2 bedrooms
2 baths
6 guests
Location Wailea, HI Icon of Ocean View Ocean View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
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Experience Wailea at its absolute best in Penthouse 508, a spectacular 2,893-square-foot residence that stands apart with a totally unique layout-perched at the top of the Wailea Beach Villas with sweeping ocean views, soaring ceilings, and a spacious design unlike anything else in the resort.This exceptional 3-bedroom + den, 3-bathroom penthouse o
Wailea Beach Villas PH508
3 Bedroom Ocean View Condo - Platinum
Rating 5 (2)
3 bedrooms
3 baths
8 guests
Location Wailea, HI Icon of Ocean View Ocean View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
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Welcome to the Makena Surf F112 Beachfront Resort, where luxury meets the ocean's edge. This stunning 3-bedroom, 2-bathroom oceanfront condo is perfect for your dream Hawaiian getaway. The spacious layout features a primary suite with a king bed, a second bedroom with a king bed, and a third bedroom with two day beds, one of which can slide out on
Makena Surf F112 Beachfront Resort
3 Bedroom Oceanfront Condo - Platinum
Rating 4.9 (20)
3 bedrooms
2 baths
7 guests
Location Wailea, HI Icon of Oceanfront View Oceanfront View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
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