Wailea Lodging
Luxury Resorts, WORLD CLASS Golf, AND Upscale Shopping
Wailea is a luxurious resort community in South Maui, renowned for its beautiful crescent shaped beaches. The area is home to several world-class golf courses, luxurious shopping, and exquisite dining options. Known for its upscale accommodations, Wailea boasts numerous resorts and vacation rentals, including family-friendly options, making it ideal for both relaxation and adventure.
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179 properties available
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Wailea Beach Villas Penthouse 302, with breathtaking views of the pristine Pacific Ocean, awaits. Take joy in the comfort of luxury and tranquility as it seamlessly infuses with lush tropical surroundings creating long lasting memories. Impeccable contemporary finishes paired with chic, natural tones and patterns further elevate the ambiance of thi
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Wailea Beach Villas (31)
Wailea Beach Villas PH302
2 Bedroom Ocean View Condo - Platinum
5
(9)
2
bedrooms
2
baths
6
guests
Wailea, HI
Ocean View
Complex Pool
Private Outdoor space
Welcome to your serene oasis at Wailea Ekahi Village 3E, a beautifully designed 1-bedroom, 1-bathroom condo nestled in the heart of Wailea. This stunning garden view condo offers a perfect blend of comfort and elegance, ideal for a relaxing getaway. Step inside to discover a spacious, open-concept living area where you can unwind on the plush sofa
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Wailea Ekahi Village (45)
Wailea Ekahi Village 3E
1 Bedroom Garden View Condo
5
(7)
1
bedrooms
1
baths
4
guests
Wailea, HI
Garden View
Complex Pool
Private Outdoor space
Welcome to your serene oasis at Wailea Elua Village 2006, a stunning 2-bedroom, 2-bathroom ocean view condo that promises an unforgettable stay. Nestled in the heart of Wailea, this meticulously designed property offers a perfect blend of luxury and comfort. Step into the open-concept living area, where the sleek, modern design is complemented by l
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Wailea Elua Village (42)
Wailea Elua Village 2006
2 Bedroom Ocean View Condo - Platinum
5
(18)
2
bedrooms
2
baths
6
guests
Wailea, HI
Ocean View
Complex Pool
Private Outdoor space
Welcome to your serene oasis at Wailea Ekahi Village 40F, a meticulously designed 1-bedroom, 1-bathroom garden view condo that promises an unforgettable stay. Nestled in the heart of Wailea, this 1,186 sq. ft. condo is perfect for up to four guests, offering a blend of comfort and luxury.Step inside to find a spacious living room with a cozy sofa b
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Wailea Ekahi Village (45)
Wailea Ekahi Village 40F
1 Bedroom Garden View Condo
4.8
(9)
1
bedrooms
1
baths
4
guests
Wailea, HI
Garden View
Complex Pool
Private Outdoor space
Welcome to Wailea Beach Villas Penthouse 105, where luxury living meets the breathtaking beauty of Maui. This elegant ocean view penthouse spans 2,500 square feet and features a spacious floor plan that flows seamlessly onto a generous lanai, providing the perfect backdrop for enjoying the island's tropical splendor.Located in a prime position with
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Wailea Beach Villas (31)
Wailea Beach Villas PH105
3 Bedroom Garden View Condo - Platinum
5
(4)
3
bedrooms
3
baths
6
guests
Wailea, HI
Complex Pool
Private Outdoor space
Resort Golf
Welcome to the Makena Surf F207, where luxury meets the ocean's edge. This beautifully renovated 2-bedroom, 2-bathroom oceanfront condo is perfect for your dream Maui getaway. The spacious 1,313 square foot open features floor-to-ceiling windows that bring the ocean views and natural lighting into the living room, kitchen, and dining area.Spend gen
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New Rental!
New Rental!
Be one of the first guests to stay in this vacation residence that just joined our rental program!
Makena Surf (23)
Makena Surf F207 Beachfront Resort
2 Bedroom Ocean Front Condo
4.9
(144)
2
bedrooms
2
baths
6
guests
Wailea, HI
Oceanfront View
Complex Pool
Private Outdoor space
Welcome to the serene and luxurious Wailea Elua Village 1603, a stunning 2-bedroom ocean front condo nestled in the heart of Maui’s resort town of Wailea. “Oceanfront” literally means that the only thing separating your ground floor lanai from the ocean is landscaped and manicured lawns! The home is highlighted by its inviting and oversized lanai.
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New Rental!
New Rental!
Be one of the first guests to stay in this vacation residence that just joined our rental program!
Wailea Elua Village (42)
Wailea Elua Village 1603
2 Bedroom Ocean Front Condo
5
(6)
2
bedrooms
2
baths
6
guests
Wailea, HI
Oceanfront View
Complex Pool
Private Outdoor space
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
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Wailea Beach Villas (31)
Wailea Beach Villas PH404
2 Bedroom Ocean View Condo - Platinum
5
(3)
2
bedrooms
2
baths
6
guests
Wailea, HI
Ocean View
Complex Pool
Private Outdoor space
Welcome to your serene oasis at Wailea Elua Village 1704, a stunning two-bedroom oceanfront condo that promises an unforgettable stay. This 1,336 square foot retreat comfortably sleeps up to six guests, making it perfect for families or groups of friends. The open-concept living area features a plush sofa bed, ideal for unwinding after a day of exp
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Wailea Elua Village (42)
Wailea Elua Village 1704
2 Bedroom Oceanfront Condo
5
(11)
2
bedrooms
2
baths
6
guests
Wailea, HI
Oceanfront View
Complex Pool
Private Outdoor space
Wailea Beach Villas Penthouse 504 enjoys 180 degree views of the Pacific Ocean, Kaho‘olawe, Molokini crater, and Lanai. This generous two-bedroom, two-bathroom condo provides over 1900 sq. ft. of living space, outdoor lanai, entertaining space, plus a den. Located on the fifth floor, guests can take advantage of the elevated views! Lounge on the s
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Wailea Beach Villas (31)
Wailea Beach Villas PH504
2 Bedroom Ocean View Condo - Platinum
5
(10)
2
bedrooms
2
baths
6
guests
Wailea, HI
Ocean View
Complex Pool
Private Outdoor space
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
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Makena Surf (23)
Makena Surf F112 Beachfront Resort
3 Bedroom Oceanfront Condo - Platinum
4.9
(21)
3
bedrooms
2
baths
7
guests
Wailea, HI
Oceanfront View
Complex Pool
Private Outdoor space
Welcome to the serene and luxurious Wailea Elua Village 1001, a stunning 2-bedroom oceanfront condo nestled in the heart of Wailea. This meticulously designed property offers a perfect blend of comfort and elegance, ideal for your dream vacation.Step inside to discover a spacious, open-plan living area that seamlessly flows into a private balcony,
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Wailea Elua Village (42)
Wailea Elua Village 1001
2 Bedroom Oceanfront Condo - Diamond
5
(19)
2
bedrooms
2
baths
4
guests
Wailea, HI
Oceanfront View
Complex Pool
Private Outdoor space
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