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Results: 854 Rentals

  • Fantastic Wailea Ekahi Beachfront Condo 45F
    From $397 per night (USD)

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    Fantastic Wailea Ekahi Beachfront Condo 45F

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    5

    Welcome to my sunny Wailea Paradise! This refreshed and tastefully decorated second-floor condo (Unit 45F) has fantastic ...

    From $397 per night (USD)

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  • Exquisite Spacious Wailea Beach Villas H102
    From $1310 per night (USD)

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    Exquisite Spacious Wailea Beach Villas H102

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Incredible Location! Ground Floor, Garden View Penthouse at the Wailea Beach Villas, steps from the pool! Beautifully a ...

    From $1310 per night (USD)

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  •  1br/1ba Condo Steps From The Pavilion pool,  Mokapu Beach with beautiful views.
    From $417 per night (USD)

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    1br/1ba Condo Steps From The Pavilion pool, Mokapu Beach with beautiful views.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This is a 1 bedroom, 1 bath upper level condo for a maximum of two people. It is well furnished and equipped, is very co ...

    From $417 per night (USD)

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  • On Wailea Blue Golf Course ⛳️with Ocean View.   🌊
    From $844 per night (USD)

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    On Wailea Blue Golf Course ⛳️with Ocean View. 🌊

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Hawaii GE & TA Tax ID # G/T 006-824-3456-01 Taxes on total amount is 17.42%. Not included in the vrbo quote. Required ...

    From $844 per night (USD)

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  • Maui Breeze Retreat at Ho'olei! Open Sep 25-Oct 14, Oct 26-Nov 7 & Nov 26-Dec 10
    From $1811 per night (USD)

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    Maui Breeze Retreat at Ho'olei! Open Sep 25-Oct 14, Oct 26-Nov 7 & Nov 26-Dec 10

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Surround yourself with the lush scenery of Maui Breeze Retreat at Ho'ol!ei, a tastefully decorated two-story villa with ...

    From $1811 per night (USD)

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  • Soooooo Close to the Beach & Completely Remodeled!  Relax to the Sound of Waves
    From $519 per night (USD)

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    Soooooo Close to the Beach & Completely Remodeled! Relax to the Sound of Waves

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    This beautiful ground floor unit was completely remodeled in 2015 and every surface is brand new. If you prefer one of ...

    From $519 per night (USD)

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  • Amazing Wailea Surf Villa: Luxury Condo - Owner Direct!
    From $1734 per night (USD)

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    Amazing Wailea Surf Villa: Luxury Condo - Owner Direct!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    'Wailea Beach Villas was named the Top Resort in Hawaii in 2014' - Conde Nast Readers Choice Award Conde Nast Traveler' ...

    From $1734 per night (USD)

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  • Remodelled 3 Bdrm Grand Champions Villa with Full Ocean View and New Central A/C
    From $582 per night (USD)

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    Remodelled 3 Bdrm Grand Champions Villa with Full Ocean View and New Central A/C

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    We're very excited to offer our returning and our new guests our Maui home, which includes full remodels to the kitchen ...

    From $582 per night (USD)

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  • The Best of 'The Palms' - Panoramic Views, Private End Unit #1102
    From $466 per night (USD)

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    The Best of 'The Palms' - Panoramic Views, Private End Unit #1102

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to paradise. A private, two bedroom, non-smoking condo at the Palms at Wailea with sweeping ocean views from Mo ...

    From $466 per night (USD)

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  • Wailea Beach Villas | B101
    From $3107 per night (USD)

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    Wailea Beach Villas | B101

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    You will feel like a rock star in this oceanfront villa that even has a vinyl record Juke box with complimentary play! V ...

    From $3107 per night (USD)

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  • Wailea Elua Village | 401
    From $1299 per night (USD)

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    Wailea Elua Village | 401

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Wailea Elua Village 401 is a stunning vacation rental situated in the luxurious Wailea area of Maui. This ground floor ...

    From $1299 per night (USD)

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  • Wailea Ekahi 45B-Summer Special 225/Nt, New Kitch, Lrg Lanai, Pool #3 w/BBQ
    From $358 per night (USD)

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    Wailea Ekahi 45B-Summer Special 225/Nt, New Kitch, Lrg Lanai, Pool #3 w/BBQ

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Unit 45B is located in Building 45 on the ground floor. This lovely one bedroom, two bathroom condo has a 400 square fo ...

    From $358 per night (USD)

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  • Prime Beachfront on the Ground Floor, Polo Beach Wailea/Makena #104
    From $1375 per night (USD)

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    Prime Beachfront on the Ground Floor, Polo Beach Wailea/Makena #104

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    The Polo Beach condos sleep 6 in total. Please call for very latest openings as there may be a new booking in progress. ...

    From $1375 per night (USD)

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  • Wailea Elua Village | 904
    From $2540 per night (USD)

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    Wailea Elua Village | 904

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Wailea Elua 904 is a stunning vacation rental property that offers a luxurious island getaway. Nestled within the upscal ...

    From $2540 per night (USD)

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  • REMODELED-LARGE LANAI-GROUND FLOOR-AC-OCEAN VIEWS-METICULOUS CLEANING
    From $791 per night (USD)

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    REMODELED-LARGE LANAI-GROUND FLOOR-AC-OCEAN VIEWS-METICULOUS CLEANING

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    6

    Book with confidence, Wailea Ekahi 46 B is a brand new luxurious 1100 sq. ft. condo. This condo is managed by PMI Maui, ...

    From $791 per night (USD)

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  • Wailea Elua Village | 707
    From $1447 per night (USD)

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    Wailea Elua Village | 707

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Ideally situated in a quiet corner along the northern edge of the resort, Wailea Elua Village 707 is just a short stroll ...

    From $1447 per night (USD)

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  • Wailea Ekahi Village | 39A
    From $928 per night (USD)

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    Wailea Ekahi Village | 39A

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    If you’re seeking privacy and relaxation, Wailea Ekahi Village 39A offers a secluded Maui retreat nestled behind a lush ...

    From $928 per night (USD)

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  • Wailea Elua Village | 2004
    From $1271 per night (USD)

    Expedia

    Wailea Elua Village | 2004

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Wailea Elua 2004 is a luxurious vacation rental located along the shores of Maui's southern coastline. This one-bedroom, ...

    From $1271 per night (USD)

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  • Wailea Ekahi Village | 11A
    From $640 per night (USD)

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    Wailea Ekahi Village | 11A

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Wailea Ekahi 11A offers a truly exceptional and luxurious island getaway on Maui. Situated in the prestigious Wailea res ...

    From $640 per night (USD)

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  • Wailea Ekahi Village | 12A
    From $971 per night (USD)

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    Wailea Ekahi Village | 12A

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Wailea Ekahi 12A is an exquisite vacation rental located within the desireable area of Wailea along Maui's southern coas ...

    From $971 per night (USD)

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  • Wailea Ekahi Village | 12C
    From $640 per night (USD)

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    Wailea Ekahi Village | 12C

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Wailea Ekahi 12C is a beautiful vacation rental nestled within the landscaped 32 acres that make up Wailea Ekahi Village ...

    From $640 per night (USD)

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  • Wailea Ekahi Village | 15A
    From $560 per night (USD)

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    Wailea Ekahi Village | 15A

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Walk to the beach in minutes from this ground floor condo at Wailea Ekahi Village. Slide open the glass lanai doors of ...

    From $560 per night (USD)

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  • Wailea Elua Village | 708
    From $1224 per night (USD)

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    Wailea Elua Village | 708

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Wailea Elua Village 708 is a luxurious two-bedroom, two-bathroom vacation rental located in the prestigious Wailea commu ...

    From $1224 per night (USD)

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  • Wailea Ekahi Village | 10F
    From $948 per night (USD)

    Expedia

    Wailea Ekahi Village | 10F

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Wailea Ekahi Village 10F is a premier vacation rental located in the heart of Wailea, Maui. This one-bedroom, two-bathro ...

    From $948 per night (USD)

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  • Wailea Elua 1308 - Direct Beachfront Luxury Condo in the Heart of Wailea, Maui
    From $1571 per night (USD)

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    Wailea Elua 1308 - Direct Beachfront Luxury Condo in the Heart of Wailea, Maui

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Introducing: Wailea Elua 1308. Offering a front row beachfront location, this immaculately maintained unit features unob ...

    From $1571 per night (USD)

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  • Wailea Ekahi Village | 3A
    From $785 per night (USD)

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    Wailea Ekahi Village | 3A

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    For a vacation condo that feels like a private home, select this two story residence with a sunken living room and casca ...

    From $785 per night (USD)

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  • Wailea Elua Village | 1103
    From $1457 per night (USD)

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    Wailea Elua Village | 1103

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Located within short walking distance to the beach and close to the on-property pickleball court and swimming pool, Wail ...

    From $1457 per night (USD)

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  • Wailea Elua Village | 1604
    From $2064 per night (USD)

    Expedia

    Wailea Elua Village | 1604

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Expansive unobstructed views of blue Pacific waters and gentle waves will greet you each time you step out onto the lana ...

    From $2064 per night (USD)

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  • Wailea Ekahi Village | 54B
    From $608 per night (USD)

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    Wailea Ekahi Village | 54B

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Wailea Ekahi 54B is a luxurious one-bedroom two-bathroom vacation rental offering an exceptional blend of comfort and el ...

    From $608 per night (USD)

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  • Fabulous Condo with Amazing Ocean Views - Building 22! Remaining 2025 $350
    From $708 per night (USD)

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    Fabulous Condo with Amazing Ocean Views - Building 22! Remaining 2025 $350

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    This is a beautiful vacation condominium in the prestigious Wailea resort area regarded as the 'sunny side' of Maui! T ...

    From $708 per night (USD)

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  • Wailea Elua Village | 1102
    From $1345 per night (USD)

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    Wailea Elua Village | 1102

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    This ocean view one-bedroom Wailea Elua Village condo is a great home base for experiencing the joys and beauty of south ...

    From $1345 per night (USD)

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  • Wailea Elua Village | 1501
    From $1247 per night (USD)

    Expedia

    Wailea Elua Village | 1501

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Wailea Elua Village 1501 is the perfect home base for exploring the sights, sounds, and tastes of Maui. This two-bedroom ...

    From $1247 per night (USD)

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  • Wailea Ekahi Village | 30D
    From $689 per night (USD)

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    Wailea Ekahi Village | 30D

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Nestled in the prestigious Wailea Ekahi Village, condo 30D is an exquisitely decorated island-inspired vacation rental t ...

    From $689 per night (USD)

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  • Wailea Ekahi Village | 20H
    From $819 per night (USD)

    Expedia

    Wailea Ekahi Village | 20H

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Discover the perfect blend of elegance and comfort at Wailea Ekahi 20H, a beautifully decorated two-bedroom, two-bathroo ...

    From $819 per night (USD)

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  • Wailea Ekahi Village | 12E
    From $658 per night (USD)

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    Wailea Ekahi Village | 12E

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Wailea Ekahi Village 12E is a delight to the senses. A vibrant row of Bougainvillea and the sweet smell of plumeria welc ...

    From $658 per night (USD)

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  • Wailea Elua Village | 1301
    From $1223 per night (USD)

    Expedia

    Wailea Elua Village | 1301

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Experience the ultimate Hawaiian getaway when vacationing at Wailea Elua 1301. This beautifully designed vacation rental ...

    From $1223 per night (USD)

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  • Luxury Vacation Rental in Wailea Beachfront - Exclusive Polo Beach Location
    From $1036 per night (USD)

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    Luxury Vacation Rental in Wailea Beachfront - Exclusive Polo Beach Location

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    The Polo Beach Club... Whether you are planning a romantic getaway for two or a family vacation, you will find everythin ...

    From $1036 per night (USD)

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  • Escape to Paradise – Your Dream Wailea Getaway Awaits!
    From $499 per night (USD)

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    Escape to Paradise – Your Dream Wailea Getaway Awaits!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Welcome to your tropical retreat at Grand Champions Villas in Wailea, where luxury meets tranquility. Imagine unwinding ...

    From $499 per night (USD)

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  • STUNNING OCEAN VIEW CONDO! Fully Remodeled! Ground!Private!Bunks!Large Lanai!
    From $683 per night (USD)

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    STUNNING OCEAN VIEW CONDO! Fully Remodeled! Ground!Private!Bunks!Large Lanai!

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    EKAHI 51B Wailea Ekahi 51B is a luxury high end condo in the highly sought after ocean front complex Wailea Ekahi Vill ...

    From $683 per night (USD)

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  • Wailea Elua Village | 2401
    From $998 per night (USD)

    Expedia

    Wailea Elua Village | 2401

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Wailea Elua 2401 is a stunning condo that features a large private wrap-around lanai with breathtaking ocean views. Co ...

    From $998 per night (USD)

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  • Best 2 Bedroom Condo In Wailea - Enjoy Paradise All Year
    From $525 per night (USD)

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    Best 2 Bedroom Condo In Wailea - Enjoy Paradise All Year

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    2

    Aloha and welcome to our home at The Palms at Wailea. The ocean view will take your breath away the minute you step ins ...

    From $525 per night (USD)

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  • Beachfront Maui Home -  4 bedroom 3 Bath
    From $3975 per night (USD)

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    Beachfront Maui Home - 4 bedroom 3 Bath

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Polo Beach House is a unique 3500 sq ft property with singular direct beach access to Polo Beach. Walk out of your oce ...

    From $3975 per night (USD)

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  • Wailea Elua Village | 1303
    From $2127 per night (USD)

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    Wailea Elua Village | 1303

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    When vacationing in Wailea Elua 1303, you’ll feel pampered by the extra touches that await you in this suite featuring m ...

    From $2127 per night (USD)

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  • Wailea Ekolu Village | 1007
    From $552 per night (USD)

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    Wailea Ekolu Village | 1007

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Experience the beauty of Maui at Wailea Ekolu 1007, a stunning two-bedroom, two-bathroom ocean view condo designed for r ...

    From $552 per night (USD)

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  • Wailea Elua Village | 2104
    From $1345 per night (USD)

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    Wailea Elua Village | 2104

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Wailea Elua 2104 is a charming two-bedroom, two-bathroom condo that comfortably accommodates up to six guests. Designed ...

    From $1345 per night (USD)

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  • Wailea Elua Village | 2006
    From $1547 per night (USD)

    Expedia

    Wailea Elua Village | 2006

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Wailea Elua Village 2006 is a charming vacation rental that epitomizes the luxury and tranquility of Maui. This beautifu ...

    From $1547 per night (USD)

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    Details
  • Wailea Elua Village | 1502
    From $1345 per night (USD)

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    Wailea Elua Village | 1502

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Situated near the center of the resort, Wailea Elua 1502 is siutated near the putting green and central swimming pool. J ...

    From $1345 per night (USD)

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  • Wailea Ekahi Village | 38F
    From $1129 per night (USD)

    Expedia

    Wailea Ekahi Village | 38F

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Nestled in the heart of Wailea, Wailea Ekahi 38F is an exquisite vacation rental that offers a luxurious and serene Maui ...

    From $1129 per night (USD)

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  • Wailea Elua Village | 1703
    From $1515 per night (USD)

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    Wailea Elua Village | 1703

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Elua 1703 is a distinctive oceanfront vacation rental, perfectly situated directly in front of the renowned Ulua Beach a ...

    From $1515 per night (USD)

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  • Wailea Elua Village | 2012
    From $844 per night (USD)

    Expedia

    Wailea Elua Village | 2012

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Wailea Elua Village 2012 is a luxurious vacation rental located in the stunning Wailea area of Maui. This one-bedroom, t ...

    From $844 per night (USD)

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  • Wailea Elua Village | 1704
    From $2017 per night (USD)

    VRBO

    Wailea Elua Village | 1704

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Wailea Elua 1704 is a stunning oceanfront vacation rental located a short stroll from one of the top snorkeling beaches ...

    From $2017 per night (USD)

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  • Wailea Beach Villas E-302 on Wailea Beach
    From $3177 per night (USD)

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    Wailea Beach Villas E-302 on Wailea Beach

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Modern living, in one of the best locations at Wailea Beach Villas, with outer island and sunset views that are unmatche ...

    From $3177 per night (USD)

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  • Luxurious Wailea Polo Beach Club Oceanfront Condo, Spectaular View
    From $796 per night (USD)

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    Luxurious Wailea Polo Beach Club Oceanfront Condo, Spectaular View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Polo #406 is a beautiful, comfortable unit overlooking the ocean. It offers breathtaking views of Molokini, West Maui, ...

    From $796 per night (USD)

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  • Steps to Ocean View Pool, Walk to Beach
    From $485 per night (USD)

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    Steps to Ocean View Pool, Walk to Beach

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Forget your worries in this spacious and serene space. First floor, family-friendly unit located steps away from a tranq ...

    From $485 per night (USD)

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  • Wailea Ekahi 48C ~ 1 Bedroom 2 Bath Wailea Condo!
    From $345 per night (USD)

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    Wailea Ekahi 48C ~ 1 Bedroom 2 Bath Wailea Condo!

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Wailea Ekahi Village - Spacious one bedroom, two bath condo with a enchanting garden view located in the Upper Village. ...

    From $345 per night (USD)

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  • Wailea Ekahi 46F Spacious 2 bedroom 2 Bath Condo in Wailea
    From $531 per night (USD)

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    Wailea Ekahi 46F Spacious 2 bedroom 2 Bath Condo in Wailea

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Wailea Ekahi - Beautiful Garden and Ocean Views from this comforting unit! Nice 2 bedroom, 2 bath condo over looking t ...

    From $531 per night (USD)

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  • Ho'olei Villas | Wailea Kapili
    From $1831 per night (USD)

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    Ho'olei Villas | Wailea Kapili

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    This residence has been given the Hawaiian name "Wailea Kapili", which translates to "a Wailea Gathering." It is the per ...

    From $1831 per night (USD)

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  • Panoramic Views - Fourth Row Ho'olei - One of a Kind 112-4
    From $1664 per night (USD)

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    Panoramic Views - Fourth Row Ho'olei - One of a Kind 112-4

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Newly Remodeled in 2023! Come relax and enjoy the spectacular ocean and island views in this rare three bedroom condo pe ...

    From $1664 per night (USD)

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  • Palms at Wailea 1201! Perfect Location in Wailea!
    From $569 per night (USD)

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    Palms at Wailea 1201! Perfect Location in Wailea!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Palms at Wailea 1201! Perfect location in Wailea! This 2-bed/2-bath condo offers the perfect getaway for families or cou ...

    From $569 per night (USD)

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  • Palms at Wailea 1203 Offers The Perfect Location in Wailea!
    From $496 per night (USD)

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    Palms at Wailea 1203 Offers The Perfect Location in Wailea!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Palms at Wailea 1203, offers the perfect location in Wailea. This 2-bedroom/2-bath ground-level unit surrounded by lush ...

    From $496 per night (USD)

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  • Wailea Ekahi Premier 1 Bd+2Ba Condominium 20G-Adjacent to Keawakapu Beach
    From $498 per night (USD)

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    Wailea Ekahi Premier 1 Bd+2Ba Condominium 20G-Adjacent to Keawakapu Beach

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Don't miss the best that Wailea Ekahi has to offer. Ekahi 20G - newly remodeled as of August 2025. Gorgeous! Stay wi ...

    From $498 per night (USD)

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  • Fully Remodeled Modern Island Style!
    From $646 per night (USD)

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    Fully Remodeled Modern Island Style!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Aloha and welcome to our condo, the Palms at Wailea 606. We’re looking forward to hosting you and making your vacation ...

    From $646 per night (USD)

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  • NEWLY REMODELED! Partial Ocean View condo along the golf course
    From $726 per night (USD)

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    NEWLY REMODELED! Partial Ocean View condo along the golf course

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This newly remodeled 3 bedroom 2 bath condo located in the heart of Wailea is the perfect vacation oasis for your island ...

    From $726 per night (USD)

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  • Dramatic Ocean Views, Wailea Ekolu 407, Perfect for Couples, Renovated, Split AC
    From $444 per night (USD)

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    Dramatic Ocean Views, Wailea Ekolu 407, Perfect for Couples, Renovated, Split AC

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Experience the essence of Maui at Wailea Ekolu 407, a luxurious 1-bedroom, 2-bathroom condo that offers breathtaking pan ...

    From $444 per night (USD)

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  • Luxury 2-Bedroom with Ocean and Fairway Views Upgraded and Beautifully Decorated
    From $416 per night (USD)

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    Luxury 2-Bedroom with Ocean and Fairway Views Upgraded and Beautifully Decorated

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Luxury awaits you in this beautifully upgraded 2-bedroom condo. Magnificent ocean and fairway views from this beachy uni ...

    From $416 per night (USD)

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  • Luxurious Wailea Ocean Vistas
    From $813 per night (USD)

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    Luxurious Wailea Ocean Vistas

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Summary: Completely remodeled (Dec 2022). Our new Wailea luxury condo is immaculate and offers direct ocean views. Airy, ...

    From $813 per night (USD)

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  • Experience Wailea Ekahi 4E, Greenbelt Location, New Split-AC, Serene & Stylish!
    From $419 per night (USD)

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    Experience Wailea Ekahi 4E, Greenbelt Location, New Split-AC, Serene & Stylish!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to Wailea Ekahi 4E, a serene one-bedroom, one-bathroom retreat nestled in the heart of Maui's lush Wailea coast. ...

    From $419 per night (USD)

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  • Elua 1310 Oceanfront - Family Managed-Full Condo Remodel Completed 9/25!
    From $1184 per night (USD)

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    Elua 1310 Oceanfront - Family Managed-Full Condo Remodel Completed 9/25!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    (9/17/25) We just wrapped a full condo remodel of our oceanfront home and am bringing the unit back online! Elua 1310 i ...

    From $1184 per night (USD)

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  • Grand Champions Condos by KBM
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    Grand Champions Condos by KBM

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    <p>You'll find snow sports gear on site at this beach apartment. Shops at Wailea is within an easy 10-minute walk and Ul ...

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  • Beautifully remodeled ocean view condo in Wailea WE27B
    From $685 per night (USD)

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    Beautifully remodeled ocean view condo in Wailea WE27B

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Hawaii Tax ID: TA-072-016-4864-01 TMK: 210080600050 Enjoy this beautifully remodeled luxury unit at Wailea Ekahi! A sh ...

    From $685 per night (USD)

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  • October LAST Minute SPECIAL !  Direct Ocean Front Prop Wailea Ekahi 42A 1 Bed/2B
    From $533 per night (USD)

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    October LAST Minute SPECIAL ! Direct Ocean Front Prop Wailea Ekahi 42A 1 Bed/2B

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Imagine waking to the gentle lull of the trade winds, sunlight streaming through your lanai, and the promise of a perfec ...

    From $533 per night (USD)

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  • Grand Champions #86 Gorgeous Views On Golf Course, Near Popular Beaches
    From $502 per night (USD)

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    Grand Champions #86 Gorgeous Views On Golf Course, Near Popular Beaches

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Wailea Grand Champions #86 is a 1 bedroom, 2 bath unit on the second floor with gorgeous ocean and golf course views. Wi ...

    From $502 per night (USD)

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  • Polo Beach Club  |  408
    From $1944 per night (USD)

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    Polo Beach Club | 408

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Polo Beach Club 408 is a stunningly renovated vacation rental that offers breathtaking ocean views, making it an ideal g ...

    From $1944 per night (USD)

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  • Wailea Ekolu 206 -Gorgeous Ocean View - AC - Close to Wailea Beach!
    From $510 per night (USD)

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    Wailea Ekolu 206 -Gorgeous Ocean View - AC - Close to Wailea Beach!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    E Komo Mai to our luxury 2 bedroom unit on the 2nd floor with a beautiful ocean view and a spacious interior. From our c ...

    From $510 per night (USD)

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  • Wailea Elua - Ocean views paradise | Pool & AC
    From $1111 per night (USD)

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    Wailea Elua - Ocean views paradise | Pool & AC

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Summary: Nestled in the scenic beauty of Wailea, this inviting condo promises a delightful escape with everything you ne ...

    From $1111 per night (USD)

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  • Elua 2303: Gorgeous Luxe Condo, Ocean Sunset Views
    From $746 per night (USD)

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    Elua 2303: Gorgeous Luxe Condo, Ocean Sunset Views

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    This property is hotel zoned, and not being affected by the recent proposed legislation. This bright and spacious condo ...

    From $746 per night (USD)

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  • Wailea Ekahi Village 43B 1Bed/2Bath near quiet pool
    From $521 per night (USD)

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    Wailea Ekahi Village 43B 1Bed/2Bath near quiet pool

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    This spacious one bedroom, two bath ground-floor condo is just steps away from one of four pools and a short walk throug ...

    From $521 per night (USD)

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  • BEAUTIFUL BRAND NEW REMODEL-OCEAN VIEWS-SLEEPS 8-AC-WELL EQUIPPED
    From $552 per night (USD)

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    BEAUTIFUL BRAND NEW REMODEL-OCEAN VIEWS-SLEEPS 8-AC-WELL EQUIPPED

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Book with confidence, this stunning, 2 bedroom, 2 bathroom spacious condo that has been newly remodeled. This condo is m ...

    From $552 per night (USD)

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  • Wailea Grand Champions | 84
    From $862 per night (USD)

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    Wailea Grand Champions | 84

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Wailea Grand Champions 84 is a beautifully appointed vacation rental located in the prestigious Wailea area of Maui. Thi ...

    From $862 per night (USD)

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  • Aloha Moon - The Honeymoon Hideaway
    From $685 per night (USD)

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    Aloha Moon - The Honeymoon Hideaway

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Escape to Aloha Moon. This calming island hideaway will have you falling in love all over again! Whether it’s your honey ...

    From $685 per night (USD)

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  • Tiki Tiki - A Gorgeous Boho Beach Hideaway!
    From $581 per night (USD)

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    Tiki Tiki - A Gorgeous Boho Beach Hideaway!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Fall in ALOHA with Tiki Tiki!! This special studio is truly a piece of Paradise! A magical retreat that will have you f ...

    From $581 per night (USD)

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  • Tropical Paradise in Luxurious 1br, 2ba Ground Floor Unit, Garden View, Palms 801
    From $338 per night (USD)

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    Tropical Paradise in Luxurious 1br, 2ba Ground Floor Unit, Garden View, Palms 801

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    3

    Welcome to Palms at Wailea 801, your ultimate tropical getaway on the island of Maui. At over 1000 square feet, our spac ...

    From $338 per night (USD)

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  • Spring Special! Fantastic Beachfront Wailea Ekahi 2/2
    From $703 per night (USD)

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    Spring Special! Fantastic Beachfront Wailea Ekahi 2/2

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to my sunny Wailea Ekahi Paradise! This unit is a remodeled, expanded and wonderfully furnished 2 bedroom 2 bath ...

    From $703 per night (USD)

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  • Wailea Point | 3203 | 30+ Night Luxury Stays
    From $771 per night (USD)

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    Wailea Point | 3203 | 30+ Night Luxury Stays

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Point #3203 offers a luxurious and serene retreat with stunning ocean views, located in the exclusive gated commu ...

    From $771 per night (USD)

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  • Maui Resort Rentals: Wailea Elua 2204 − Luxuriously Remodeled 2BR w/ Stunning Ocean Views, New Listing!
    From $1171 per night (USD)

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    Maui Resort Rentals: Wailea Elua 2204 − Luxuriously Remodeled 2BR w/ Stunning Ocean Views, New Listing!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Boasting stunning panoramic views of the Pacific Ocean that extend deep into the home's living, kitchen, and dining area ...

    From $1171 per night (USD)

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  • Charming Oceanview Oasis: Wailea Elua 802 Surrounded by Lush Tropical Grounds
    From $1042 per night (USD)

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    Charming Oceanview Oasis: Wailea Elua 802 Surrounded by Lush Tropical Grounds

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Wailea Elua #802 – Panoramic Oceanfront Luxury, Fully Remodeled in November 2024 Welcome to Wailea Elua #802, a stunnin ...

    From $1042 per night (USD)

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  • Gorgeous Beachfront Condo in Wailea with Private Lanai
    From $335 per night (USD)

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    Gorgeous Beachfront Condo in Wailea with Private Lanai

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    *Please note Ekahi Village is a non-smoking community. Smoking is not permitted anywhere on property including patio/lan ...

    From $335 per night (USD)

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  • Gem near Keawakapu Beach - Privacy, Ocean Views, Split A/C
    From $678 per night (USD)

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    Gem near Keawakapu Beach - Privacy, Ocean Views, Split A/C

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    The Palms at Wailea #2204 has been totally remodeled. This large condo of 1022 sq feet has soaring ceilings and stunning ...

    From $678 per night (USD)

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  • 2024 Remodel! Brand New Luxury!  Ocean View!  Sleeps 5! Remaining 2025 $225
    From $545 per night (USD)

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    2024 Remodel! Brand New Luxury! Ocean View! Sleeps 5! Remaining 2025 $225

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    EKAHI's NEWEST LUXURY REMODEL WITH INCREDIBLE OCEAN VIEW! This is a beautiful vacation condominium in the prestigious W ...

    From $545 per night (USD)

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  • Gorgeous Expansive Condo in Wailea with HUGE Lanai & Ocean Views
    From $642 per night (USD)

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    Gorgeous Expansive Condo in Wailea with HUGE Lanai & Ocean Views

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Address for this Condo: Wailea Ekahi, 3300 Wailea Alanui Dr. (Unit 51A), Kihei HI 96753 ***Professionally Cleaned Condo ...

    From $642 per night (USD)

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  • Ho'olei Garden View by Coldwell Banker Island Vacation
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    Ho'olei Garden View by Coldwell Banker Island Vacation

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    <p>Close to fishing, hiking and biking trails, and more, this smoke-free villa brings it all within reach. Wailea Beach ...

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  • Tropical Wailea Retreat
    From $455 per night (USD)

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    Tropical Wailea Retreat

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    We invite you to come and stay at our spacious suite where you can enjoy the exclusive Wailea lifestyle. Relax & restore ...

    From $455 per night (USD)

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  • KBM Resorts | FREE CAR | Grand Champions | Remodeled 2-Bedroom Villa in the Heart of Wailea! GCH-120
    From $772 per night (USD)

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    KBM Resorts | FREE CAR | Grand Champions | Remodeled 2-Bedroom Villa in the Heart of Wailea! GCH-120

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Renovated 2-bedroom, 2-bath villa at Grand Champions Resort with ocean views, pools, tennis, shopping, and dining-perfec ...

    From $772 per night (USD)

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  • Panoramic Ocean View Condo on Golf Course close to Beaches
    From $582 per night (USD)

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    Panoramic Ocean View Condo on Golf Course close to Beaches

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Our townhouse in the Wailea Ekolu Place located on the Wailea Blue Golf Course. It has a spectacular view and large lana ...

    From $582 per night (USD)

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  • WEK 37C Wailea Retreat w AC Pool Near Beach Golf
    From $412 per night (USD)

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    WEK 37C Wailea Retreat w AC Pool Near Beach Golf

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Wailea Ekahi 37C Experience the Luxury of Wailea at Updated 1Bedroom Condo with Split AC Throughout and Comfortably Furn ...

    From $412 per night (USD)

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  • Grand Champions #57 Gorgeous High-end Wailea Suite on Ground Floor, Full A/C
    From $473 per night (USD)

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    Grand Champions #57 Gorgeous High-end Wailea Suite on Ground Floor, Full A/C

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Grand Champions #57 is a spacious, bright and airy 1Bd/2Ba unit on the ground floor. It features window unit air conditi ...

    From $473 per night (USD)

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  • Wailea Ekahi Two Bedrooms - Garden View by Coldwell Banker Island Vacations
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    Wailea Ekahi Two Bedrooms - Garden View by Coldwell Banker Island Vacations

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    <p>Close to sailing, cycling, and more, this smoke-free condo brings it all within reach. There's convenient onsite park ...

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  • Wailea Ekahi One Bedrooms - Ocean View by Coldwell Banker Island Vacations
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    Wailea Ekahi One Bedrooms - Ocean View by Coldwell Banker Island Vacations

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    <p>Close to sailing, cycling, and more, this smoke-free condo brings it all within reach. Ulua Beach Park is just steps ...

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  • Wailea Ekahi One Bedrooms - Garden View by Coldwell Banker Island Vacations
    From $993 per night (USD)

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    Wailea Ekahi One Bedrooms - Garden View by Coldwell Banker Island Vacations

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    <p>A short distance from sailing, cycling, and more, this smoke-free condo lets you experience it all. Shops at Wailea i ...

    From $993 per night (USD)

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  • Polo Beach Club Two Bedrooms - Sleeps 6 by Coldwell Banker Island Vacations
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    Polo Beach Club Two Bedrooms - Sleeps 6 by Coldwell Banker Island Vacations

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    <p>Close to fishing, this smoke-free condo brings it all within reach. Polo Beach is just steps away while Wailea Beach ...

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