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  • Beautiful Sunsets with this Ocean View Condo!
    From $409 per night (USD)

    VRBO

    Beautiful Sunsets with this Ocean View Condo!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This beautiful top floor, Grand Champs condo has one of the best ocean views in the complex. This fully updated 2 bedro ...

    From $409 per night (USD)

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    Details
  • \Sunsational\Oceanfront Living& Views over your soft sand Beach just steps away.
    From $1625 per night (USD)

    Expedia

    \"Sunsational\"Oceanfront Living& Views over your soft sand Beach just steps away.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Enhance your island stay and experience breathtaking views at every turn while enjoying lavish extras and carefree upsca ...

    From $1625 per night (USD)

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  • 2BR, 2 BA Ocean View,  Everything you need is here!
    From $299 per night (USD)

    VRBO

    2BR, 2 BA Ocean View, Everything you need is here!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This is our 2nd Floor, Ocean view condo. There is a condo above this unit. You have a designated parking spot directly ...

    From $299 per night (USD)

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  • Wailea Ekahi 33c Ocean View Condo - 500 Feet from the Beach!
    From $520 per night (USD)

    VRBO

    Wailea Ekahi 33c Ocean View Condo - 500 Feet from the Beach!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to this Wailea Ekahi Condo (Unit 33C -LINKS TO OUR PERSONAL WEBSITE ARE LOCATED BELOW). Our one bedroom, one bat ...

    From $520 per night (USD)

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  • Wailea Sensation Vacation! Spectacular Oceanview Villa! On the 2nd hole.
    From $297 per night (USD)

    VRBO

    Wailea Sensation Vacation! Spectacular Oceanview Villa! On the 2nd hole.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    The tropical splendor surrounding Grand Champion Villas is a paradise. Wailea, near Kihei is where you can play 54 ho ...

    From $297 per night (USD)

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  • Wailea Ekahi 54A:  Completely Remodeled & Panoramic Ocean View
    From $643 per night (USD)

    Expedia

    Wailea Ekahi 54A: Completely Remodeled & Panoramic Ocean View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Our Family has Two - Two Bedroom/Two Bathroom Units above and Below Each other in Ekahi Village. This is great for Fami ...

    From $643 per night (USD)

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  • Palms at Wailea 901 - Luxuriously Decorated Spacious Unit w/ Large Private Lanai
    From $448 per night (USD)

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    Palms at Wailea 901 - Luxuriously Decorated Spacious Unit w/ Large Private Lanai

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Hawaii Tax ID: TA-144-497-4592-01 QUIET PRIVACY IN PARADISE The Palms #901 is a luxurious one-bedroom two-bath groun ...

    From $448 per night (USD)

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  • Ocean View, Air Conditioned, 2 level Wailea Townhouse
    From $423 per night (USD)

    VRBO

    Ocean View, Air Conditioned, 2 level Wailea Townhouse

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Our spacious Wailea Ekolu Condominium is fully appointed and includes phone, radio, CD/DVD player, cable TV, and WiFi In ...

    From $423 per night (USD)

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    Details
  • Sweeping Ocean Views, High-end, Private, Prime Location, Deal!
    From $444 per night (USD)

    VRBO

    Sweeping Ocean Views, High-end, Private, Prime Location, Deal!

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    3

    Unit: Wailea Ekolu 507 | Maui Guidebook Committed To Clean We’re committed to enhanced cleaning protocols developed in ...

    From $444 per night (USD)

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    Details
  • Wailea Ekahi #8-B Partial Ocean View, Steps to Beach, Easy access to Pool
    From $759 per night (USD)

    VRBO

    Wailea Ekahi #8-B Partial Ocean View, Steps to Beach, Easy access to Pool

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    1 Bedroom Condo, Steps to Keawakapu Beach, 60 steps to Oceanfront Pool. This ground floor one bedroom two bath has a/c t ...

    From $759 per night (USD)

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  • FUN IN THE SUN LUXURY AT SUN SPLASH C301 AT WAILEA BEACH VILLAS!
    From $2742 per night (USD)

    VRBO

    FUN IN THE SUN LUXURY AT SUN SPLASH C301 AT WAILEA BEACH VILLAS!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Our collection of Maui vacation residences are HOTEL-Zoned or have LEGAL short-term rental permits. Reserve with Private ...

    From $2742 per night (USD)

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  • Exclusive Gated Paradise Ho'olei Villa and Private Elevator w/ Resort Amenities!
    From $1349 per night (USD)

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    Exclusive Gated Paradise Ho'olei Villa and Private Elevator w/ Resort Amenities!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    This property is hotel zoned, and not being affected by the recent proposed legislation. Breathtaking Views and Picture ...

    From $1349 per night (USD)

    Expedia

    Details
  • Up to 25% off for open dates in 2025! - Elua Village 701, Luxury 2BR, Ocean View
    From $840 per night (USD)

    VRBO

    Up to 25% off for open dates in 2025! - Elua Village 701, Luxury 2BR, Ocean View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Aloha! We are Julie and Randy and welcome to our home! We want you to enjoy the fantastic ocean views and luxury of our ...

    From $840 per night (USD)

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    Details
  • Designer - Best View!Ground Flr 2 Bdm/2Bth 39c! Remaining 2025 $400
    From $628 per night (USD)

    Expedia

    Designer - Best View!Ground Flr 2 Bdm/2Bth 39c! Remaining 2025 $400

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    7

    Wailea Ekahi Unit 39C is a beautiful vacation condominium in the prestigious Wailea resort area regarded as the 'sunny s ...

    From $628 per night (USD)

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    Details
  • Wailea, Oceanfront, Polo Beach Club Condo #403
    From $973 per night (USD)

    VRBO

    Wailea, Oceanfront, Polo Beach Club Condo #403

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Location, location, location…. Polo Beach is the premiere condominium that sits at the south end of the Wailea Beach wal ...

    From $973 per night (USD)

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  • 1A Newly renovated w/porcelain tile floors, custom cabinets, granite countertops
    From $550 per night (USD)

    Expedia

    1A Newly renovated w/porcelain tile floors, custom cabinets, granite countertops

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Unit 1A is located on beautiful Keawakapu Beach in gorgeous Wailea. This recently major renovated lower village, ground ...

    From $550 per night (USD)

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  • Fantastically Remodeled Condo with Huge Ocean Views
    From $427 per night (USD)

    VRBO

    Fantastically Remodeled Condo with Huge Ocean Views

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Aloha! Welcome to magical, mystical, mythical Maui. My intimate, meticulously maintained one bedroom two bath condo is l ...

    From $427 per night (USD)

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    Details
  • SANDY Ocean Front Property Wailea Ekahi 16A 2 Bed 2 Full Bath Ocean Views 5star
    From $1137 per night (USD)

    Expedia

    SANDY Ocean Front Property Wailea Ekahi 16A 2 Bed 2 Full Bath Ocean Views 5star

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    5-Star - Unit 16A: 2 Bed/2 Bath. Ocean Front Property - Ocean Views: Imagine waking to the gentle lull of trade winds ...

    From $1137 per night (USD)

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

    VRBO

    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)

    Expedia

    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)

    VRBO

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

    VRBO

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

    VRBO

    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)

    Expedia

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

    VRBO

    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)

    VRBO

    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)

    VRBO

    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 Ekahi 17E | Resort Level Amenities!
    From $403 per night (USD)

    VRBO

    Wailea Ekahi 17E | Resort Level Amenities!

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    The beauty of sand and sparkling waters and the warm Hawaiian sun is calling your name! Wailea Ekahi 17E is a one bedroo ...

    From $403 per night (USD)

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

    VRBO

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

    Expedia

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

    VRBO

    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)

    VRBO

    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)

    VRBO

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

    Expedia

    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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  • Redesigned Penthouse! Wailea Beach Villas J106
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    Redesigned Penthouse! Wailea Beach Villas J106

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This property is hotel zoned, and not being affected by the recent proposed legislation. Gorgeous new furnishings throu ...

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

    Expedia

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

    VRBO

    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)

    Expedia

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

    VRBO

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

    Expedia

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

    VRBO

    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)

    Expedia

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

    VRBO

    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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    Details
  • 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)

    Expedia

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

    VRBO

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

    Expedia

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

    VRBO

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

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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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    Details
  • 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)

    Expedia

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

    VRBO

    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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    Details
  • 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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    VRBO

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

    Expedia

    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)

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    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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    Details
  • 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)

    Expedia

    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)

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    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 Elua Village | 1504
    From $1254 per night (USD)

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    Wailea Elua Village | 1504

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Elua Village 1504 is a luxurious vacation rental located in the picturesque Wailea area of Maui. This beautifully ...

    From $1254 per night (USD)

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

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    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)

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    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)

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    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)

    Expedia

    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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  • Palms at Wailea #1207 Ground Floor Unit, Near Complex Pool and Shared Hot Tub
    From $527 per night (USD)

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    Palms at Wailea #1207 Ground Floor Unit, Near Complex Pool and Shared Hot Tub

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Palms at Wailea #1207 is a lovely ground-floor unit at a much sought-after complex. It is a spacious 2 bedroom, 2 bath u ...

    From $527 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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    Details
  • 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)

    Expedia

    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 ...

    Click For Pricing

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

    Expedia

    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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  • Kihei Kai Nani 238 - Garden View 1 Bedroom, Split AC, Steps to Kamaole II Beach!
    From $345 per night (USD)

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    Kihei Kai Nani 238 - Garden View 1 Bedroom, Split AC, Steps to Kamaole II Beach!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Tucked away within the quiet rearward part of this tranquil, low-rise resort and nestled in the Maui tropical greenery t ...

    From $345 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)

    Expedia

    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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  • Grand Champions Villas 125, AC, King size Bed, close to Maui's best beaches!
    From $403 per night (USD)

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    Grand Champions Villas 125, AC, King size Bed, close to Maui's best beaches!

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    We are located in the heart of Wailea at the Grand Champion Villas, close to Maui's best beaches and within walking dist ...

    From $403 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)

    Expedia

    Details