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Results: 897 Rentals

  • Wailea Ekahi Village | 8D
    From $468 per night (USD)

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    Wailea Ekahi Village | 8D

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Ekahi 8D is an exquisite vacation rental located in the serene Wailea Ekahi Village. This spacious one-bedroom, t ...

    From $468 per night (USD)

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  • Wailea Ekahi Village | 4B
    From $405 per night (USD)

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    Wailea Ekahi Village | 4B

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Wailea Ekahi 4B is a charming ground-floor vacation studio nestled on a gentle slope in the picturesque Wailea Ekahi Vil ...

    From $405 per night (USD)

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  • Wailea Ekahi Village | 19B
    From $702 per night (USD)

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    Wailea Ekahi Village | 19B

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Wailea Ekahi Village 19B is a two-story, two-bedroom, two-and-a-half-bath townhome that comfortably accommodates up to f ...

    From $702 per night (USD)

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  • Wailea Elua Village | 2008
    From $824 per night (USD)

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    Wailea Elua Village | 2008

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Elua Village 2008 is a luxurious vacation rental situated along the southern coastline of Maui in the desirable W ...

    From $824 per night (USD)

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    Details
  • Wailea Ekahi Village | 3E
    From $456 per night (USD)

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    Wailea Ekahi Village | 3E

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Ekahi 3E is a charming one-bedroom vacation rental located in the picturesque Wailea Ekahi Village. Situated on t ...

    From $456 per night (USD)

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  • Wailea Ekolu Village | 104
    From $411 per night (USD)

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    Wailea Ekolu Village | 104

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Ekolu 104 is a stunning ocean view vacation rental that features two bedrooms and two bathrooms, accommodating up ...

    From $411 per night (USD)

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  • Wailea Grand Champions | 97
    From $421 per night (USD)

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    Wailea Grand Champions | 97

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Grand Champions 97 is a premier vacation rental located in the serene tourist retreat of Wailea. This exquisite p ...

    From $421 per night (USD)

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  • Wailea Ekahi Village | 29D
    From $543 per night (USD)

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    Wailea Ekahi Village | 29D

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This Wailea Ekahi Village residence completed a beautiful renovation in 2022. From colorful artwork to comfortable and s ...

    From $543 per night (USD)

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  • Wailea Grand Champions | 104
    From $427 per night (USD)

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    Wailea Grand Champions | 104

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Villa 104 at Wailea Grand Champions Villas is a beautiful Maui vacation rental that offers an exceptional blend of style ...

    From $427 per night (USD)

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  • Wailea Grand Champions | 140
    From $547 per night (USD)

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    Wailea Grand Champions | 140

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Wailea Grand Champions 140 is a remarkable vacation rental nestled in the upscale Wailea community of Maui. This charmin ...

    From $547 per night (USD)

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    Details
  • Wailea Ekahi Village | 44B
    From $405 per night (USD)

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    Wailea Ekahi Village | 44B

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    For travelers seeking a budget-friendly option in the prestigious Wailea area without sacrificing comfort or location, W ...

    From $405 per night (USD)

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  • Wailea Ekahi Village | 22F
    From $647 per night (USD)

    Expedia

    Wailea Ekahi Village | 22F

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Wailea Ekahi 22F is located in an ideal location, closest on property (a short walk) to Keawakapu Beach and the Wailea E ...

    From $647 per night (USD)

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  • Wailea Grand Champions | 159
    From $666 per night (USD)

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    Wailea Grand Champions | 159

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Wailea Grand Champions 159 is a beautifully updated three-bedroom vacation rental located along the fairway of the Waile ...

    From $666 per night (USD)

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  • Wailea Grand Champions | 116
    From $416 per night (USD)

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    Wailea Grand Champions | 116

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Grand Champions 116 is a luxurious vacation rental located along the southern coast of Maui in the desirable tour ...

    From $416 per night (USD)

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    Details
  • Wailea Ekahi Village | 25D
    From $468 per night (USD)

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    Wailea Ekahi Village | 25D

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Wailea Ekahi 25D, an exquisite vacation rental that embodies the essence of luxurious island living in Wailea ...

    From $468 per night (USD)

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  • Wailea Grand Champions | 73
    From $465 per night (USD)

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    Wailea Grand Champions | 73

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Grand Champions Villa 73 is a recently renovated vacation rental that offers a perfect blend of luxury, comfort, ...

    From $465 per night (USD)

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    Details
  • Wailea Grand Champions | 121
    From $410 per night (USD)

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    Wailea Grand Champions | 121

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Grand Champions 121 is ground-floor vacation bliss. Enjoy the easy convenience of transporting beach equipment, g ...

    From $410 per night (USD)

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    Details
  • Wailea Ekahi Village | 40F
    From $438 per night (USD)

    Expedia

    Wailea Ekahi Village | 40F

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Discover the charm of Maui from the comfort of Wailea Ekahi 40F, a beautifully appointed one-bedroom, one-bathroom condo ...

    From $438 per night (USD)

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  • Wailea Grand Champions | 71
    From $568 per night (USD)

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    Wailea Grand Champions | 71

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Wailea Grand Champions 71 is a beautifully updated ground-floor vacation rental that offers both fairway and ocean views ...

    From $568 per night (USD)

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  • Wailea Grand Champions | 181
    From $419 per night (USD)

    Expedia

    Wailea Grand Champions | 181

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Grand Champion Villa 181 is a charming one-bedroom, two-bath vacation rental condo located in the prestigious Wailea are ...

    From $419 per night (USD)

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  • Wailea Grand Champions | 152
    From $426 per night (USD)

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    Wailea Grand Champions | 152

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Relax on your private lanai at Grand Champions #152, perched upon the second-floor, and enjoy views of manicured fairway ...

    From $426 per night (USD)

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  • Wailea Beach Villas | PH502
    From $1944 per night (USD)

    Expedia

    Wailea Beach Villas | PH502

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Wailea Beach Villas Penthouse 502 boasts a panoramic ocean vista, ideal for whale watching in the winter, and with spect ...

    From $1944 per night (USD)

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  • Wailea Beach Villas | PH201
    From $2355 per night (USD)

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    Wailea Beach Villas | PH201

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Call this private piece of paradise home, which features panoramic views of Maui and the ocean below as well as luxuriou ...

    From $2355 per night (USD)

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    Details
  • Wailea Grand Champions | 31
    From $517 per night (USD)

    Expedia

    Wailea Grand Champions | 31

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Wailea Grand Champions 31 is a recently updated vacation rental that offers a perfect blend of comfort, style, and conve ...

    From $517 per night (USD)

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    Details
  • Wailea Grand Champions | 95
    From $580 per night (USD)

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    Wailea Grand Champions | 95

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Do your Maui vacation right! Wailea Grand Champions 95 is surrounded by tropical landscaping and rolling green fairways, ...

    From $580 per night (USD)

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  • Wailea Beach Villas | PH104
    From $1973 per night (USD)

    Expedia

    Wailea Beach Villas | PH104

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Marvel at the sophisticated style and décor of Wailea Beach Villas Penthouse 104, where a touch of Bali influence seamle ...

    From $1973 per night (USD)

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    Details
  • Wailea Grand Champions | 185
    From $612 per night (USD)

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    Wailea Grand Champions | 185

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This two-bedroom, two-bath villa at Wailea Grand Champions offers a perfect blend of contemporary style and tropical par ...

    From $612 per night (USD)

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  • Wailea Beach Villas | PH411
    From $1887 per night (USD)

    Expedia

    Wailea Beach Villas | PH411

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Let the sounds of palm fronds brushing against each other in the gentle trade winds sing you to sleep this vacation. Wit ...

    From $1887 per night (USD)

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    Details
  • Wailea Ekahi Village | 42C
    From $502 per night (USD)

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    Wailea Ekahi Village | 42C

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This 1,090 square foot one-bedroom, two bathroom vacation rental sleeps four comfortably. Wailea Ekahi Village 42C is co ...

    From $502 per night (USD)

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  • Wailea Grand Champions | 111
    From $548 per night (USD)

    Expedia

    Wailea Grand Champions | 111

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Wailea Grand Champions Villa 111 is a spacious two-bedroom, two-bath vacation rental condo that accommodates up to six g ...

    From $548 per night (USD)

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    Details
  • Wailea Ekahi Village | 35C
    From $435 per night (USD)

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    Wailea Ekahi Village | 35C

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Ekahi 35C is a stunning vacation rental located in the desirable Wailea community. This beautifully appointed one ...

    From $435 per night (USD)

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    Details
  • Wailea Ekahi Village | 34E
    From $524 per night (USD)

    Expedia

    Wailea Ekahi Village | 34E

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Ekahi 34E is a charming second-floor suite that offers breathtaking ocean views of Molokini and Kaho'olawe. You ...

    From $524 per night (USD)

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    Details
  • Wailea Grand Champions | 183
    From $557 per night (USD)

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    Wailea Grand Champions | 183

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to Wailea Grand Champions 183, a luxurious vacation rental that perfectly blends comfort and style in the heart ...

    From $557 per night (USD)

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  • Wailea Grand Champions | 177
    From $421 per night (USD)

    Expedia

    Wailea Grand Champions | 177

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Maui's Wailea Grand Champions, a paradise nestled in the heart of Wailea. This exquisite one-bedroom, two-bat ...

    From $421 per night (USD)

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    Details
  • Wailea Beach Villas | PH207
    From $1932 per night (USD)

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    Wailea Beach Villas | PH207

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    6

    Upon entering your Wailea Beach Villas Ph207, you'll be captivated by the open floor plan, which seamlessly integrates a ...

    From $1932 per night (USD)

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  • Wailea Ekahi Village | 3C
    From $444 per night (USD)

    Expedia

    Wailea Ekahi Village | 3C

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Wailea Ekahi 3C is a captivating vacation rental that offers a truly idyllic island getaway in the heart of Maui's pictu ...

    From $444 per night (USD)

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    Details
  • Wailea Elua Village | 104
    From $820 per night (USD)

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    Wailea Elua Village | 104

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Elua Village 104 is a stunning Wailea condominium rental that offers a truly unparalleled Hawaii vacation experie ...

    From $820 per night (USD)

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  • Wailea Elua Village | 1607
    From $1468 per night (USD)

    Expedia

    Wailea Elua Village | 1607

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Wailea Elua 1607 is a luxurious ground floor oceanfront vacation rental located in the exclusive Wailea Elua Village. Th ...

    From $1468 per night (USD)

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  • Immaculate Wailea Point 3 Bedroom\/3+ Bath Oceanview Condominium
    From $2194 per night (USD)

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    Immaculate Wailea Point 3 Bedroom\/3+ Bath Oceanview Condominium

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    6

    Stay here for the Holidays. Please call or email us about the dates for your visit. You are welcome to island-hop or c ...

    From $2194 per night (USD)

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  • XMAS\/NYE FAMILY FUN & LUXURY ANDAZ PENTHOUSE OCEAN & SUNSET VIEWS FROM LANAI HOT TUB 3 Br\/4 Ba for 8
    From $3946 per night (USD)

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    XMAS\/NYE FAMILY FUN & LUXURY ANDAZ PENTHOUSE OCEAN & SUNSET VIEWS FROM LANAI HOT TUB 3 Br\/4 Ba for 8

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    8

    The Beach Suite Villa 803 at the prestigious Andaz Maui at Wailea Resort is a BRAND NEW, privately owned luxury residenc ...

    From $3946 per night (USD)

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  • Luxurious Maui Living at Palms 203
    From $643 per night (USD)

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    Luxurious Maui Living at Palms 203

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Experience luxurious Maui living at its finest in this exquisitely remodeled 2-bedroom, 2-bathroom condo at the prestigi ...

    From $643 per night (USD)

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  • Beautiful Wailea: Home away from home, 2-bedroom condo
    Click For Pricing

    Expedia

    Beautiful Wailea: Home away from home, 2-bedroom condo

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Your tropical escape at Grand Champions Villas, a premier vacation rental nestled in the lush landscape of Wailea. This ...

    Click For Pricing

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  • Palms at Wailea Villa 806 Ocean View 2BD 2BA
    From $756 per night (USD)

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    Palms at Wailea Villa 806 Ocean View 2BD 2BA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    - 2nd floor, walk-up unit - Renovated Kitchen includes stovetop, oven, microwave, refrigerator, dishwasher, coffeemaker ...

    From $756 per night (USD)

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  • Wailea Elua 702 - Beautifully Renovated, Stunning Ocean Views, Central AC, Wi-Fi
    From $1303 per night (USD)

    Expedia

    Wailea Elua 702 - Beautifully Renovated, Stunning Ocean Views, Central AC, Wi-Fi

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to Wailea Elua Village 702, your perfect island retreat! This beautifully remodeled 2-bedroom, 2-bath ocean view ...

    From $1303 per night (USD)

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  • New! Palms 702 - Romantic Retreat - Split AC in Bedroom - Open-Air Living Area
    From $396 per night (USD)

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    New! Palms 702 - Romantic Retreat - Split AC in Bedroom - Open-Air Living Area

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Escape to a dreamy island getaway designed for romance and relaxation. This chic 1BR/2BA condo offers a serene ambiance ...

    From $396 per night (USD)

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  • Wailea Beach Villas | PH105
    From $2392 per night (USD)

    Expedia

    Wailea Beach Villas | PH105

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to Wailea Beach Villas Penthouse 105, where luxury living meets the breathtaking beauty of Maui. This elegant oc ...

    From $2392 per night (USD)

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    Details
  • Wailea Ekahi Village | 35D
    From $549 per night (USD)

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    Wailea Ekahi Village | 35D

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Make your Maui dreams come true at Wailea Ekahi 35D! This vacation rental is perched on the top floor with a private ent ...

    From $549 per night (USD)

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  • Gorgeous condo in a beachfront Wailea resort
    From $813 per night (USD)

    Expedia

    Gorgeous condo in a beachfront Wailea resort

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Modern Condo - Beachfront Community - Phenomenal Location! Experience luxury and tranquility at Wailea Ekahi 24B, wher ...

    From $813 per night (USD)

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    Details
  • Wailea Ekahi Studio #52-E Beautifully Renovated Studio on Keawakapu Beach
    From $583 per night (USD)

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    Wailea Ekahi Studio #52-E Beautifully Renovated Studio on Keawakapu Beach

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Wailea Ekahi #52E is a beautifully renovated studio condo with tropical garden views. The complex is nicely situated nea ...

    From $583 per night (USD)

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  • Majestic Golf Course & Sweeping Ocean Vistas at Wailea Ekolu 312
    From $548 per night (USD)

    Expedia

    Majestic Golf Course & Sweeping Ocean Vistas at Wailea Ekolu 312

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Notes from the Owner: Come relax in the luxury and tropical splendor of Maui's premier resort, Wailea. Featuring miles ...

    From $548 per night (USD)

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    Details
  • Wailea Ekolu 106 | Serene Views + Access to Pool!
    From $506 per night (USD)

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    Wailea Ekolu 106 | Serene Views + Access to Pool!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Start your morning with an open-air breakfast on the sheltered lanai, overlooking palm trees and the vibrant Pacific Oce ...

    From $506 per night (USD)

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  • Panoramic Ocean Views! Remodeled\/Redecorated! Very Pretty Corner Ground Floor 2 bedroom\/2 bath
    From $1423 per night (USD)

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    Panoramic Ocean Views! Remodeled\/Redecorated! Very Pretty Corner Ground Floor 2 bedroom\/2 bath

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $1423 per night (USD)

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  • Wailea Elua Village | 905
    From $1132 per night (USD)

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    Wailea Elua Village | 905

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Wailea Elua 905 is a vacation rental situated in the picturesque beach locale of Maui. This spacious three-bedroom, two- ...

    From $1132 per night (USD)

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    Details
  • KBM Resorts: Wailea Beach Villa, WBV-PH412 Spacious w\/sweeping Ocean Views, Includes Rental Car!
    From $4187 per night (USD)

    Expedia

    KBM Resorts: Wailea Beach Villa, WBV-PH412 Spacious w\/sweeping Ocean Views, Includes Rental Car!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    6

    FREE Rental Car! Beautifully Appointed 3 Bedroom Wailea Villa, large balcony with sweeping ocean views, a/c, easy local ...

    From $4187 per night (USD)

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  • Tropical setting on the Wailea Blue Golf Course
    From $521 per night (USD)

    VRBO

    Tropical setting on the Wailea Blue Golf Course

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to your tropical retreat in the heart of Wailea at Ekolu 1602! This second-floor condo is a 2-bedroom, 2-bathroo ...

    From $521 per night (USD)

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  • Beautiful Palms at Wailea Condo!
    From $526 per night (USD)

    Expedia

    Beautiful Palms at Wailea Condo!

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Escape to paradise at The Palms at Wailea Hotel & Resort! Our Mediterranean-style condo rental is nestled on a hillside, ...

    From $526 per night (USD)

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  • Unbeatable Ocean-View Condo in Palms at Wailea
    From $611 per night (USD)

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    Unbeatable Ocean-View Condo in Palms at Wailea

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Discover the pinnacle of luxury island living in Wailea Maui, where this newly remodeled 2-bedroom, 2-bathroom condo in ...

    From $611 per night (USD)

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  • Beautiful 2 Bed\/2Bath Ocean View Condo
    From $842 per night (USD)

    Expedia

    Beautiful 2 Bed\/2Bath Ocean View Condo

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Wailea Elua! This 2 bedroom/2 bathroom condo is the perfect location for your dream Maui vacation! The update ...

    From $842 per night (USD)

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    Details
  • Fully Remodeled Elegance in Wailea 2Bed 2Bath
    From $524 per night (USD)

    VRBO

    Fully Remodeled Elegance in Wailea 2Bed 2Bath

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to The Palms at Wailea, where we offer you exceptional experiences in a variety of realms that exceed your expec ...

    From $524 per night (USD)

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  • Spend winter in Wailea!
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    Expedia

    Spend winter in Wailea!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    2

    Fantastic like new , only 4 years old Condo with almost a 180 degree view of the ocean Private elevator takes you to the ...

    Click For Pricing

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    Details
  • Wailea Grand Champions | 52
    From $539 per night (USD)

    VRBO

    Wailea Grand Champions | 52

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to your dream vacation in Wailea, Maui! This beautiful two-bedroom residence combines comfort, style, and conven ...

    From $539 per night (USD)

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    Details
  • Wailea Ekahi Village | 17B
    From $446 per night (USD)

    Expedia

    Wailea Ekahi Village | 17B

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to Wailea Ekahi 17B, a one-bedroom residence in beautiful Wailea! This vacation rental offers a spacious and com ...

    From $446 per night (USD)

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  • Wailea Ekahi Village | 18C
    From $439 per night (USD)

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    Wailea Ekahi Village | 18C

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    E Komo Mai. Welcome to Wailea Ekahi Village 18C, a delightful one-bedroom vacation rental located in the stunning Wailea ...

    From $439 per night (USD)

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  • Wailea Ekahi Village | 38B
    From $517 per night (USD)

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    Wailea Ekahi Village | 38B

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy a relaxing indoor/outdoor tropical vacation experience from this ground floor ocean view vacation rental. Start yo ...

    From $517 per night (USD)

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  • New Listing! GC 29- Sophisticated Comfort in Favorite Wailea Town!
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    New Listing! GC 29- Sophisticated Comfort in Favorite Wailea Town!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Modern and sophisticated with a splash of Aloha, #29 is an ideal spot for honeymooning couples and those returning for t ...

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  • Wailea Luxury Resort Vista
    From $1086 per night (USD)

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    Wailea Luxury Resort Vista

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Summary: Completely remodeled (Sept 2023). Our new Wailea luxury condo is immaculate and offers direct ocean views. Airy ...

    From $1086 per night (USD)

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  • New Listing! Palms at Wailea 1501! Ground floor with Ocean views!
    From $768 per night (USD)

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    New Listing! Palms at Wailea 1501! Ground floor with Ocean views!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to our magnificent Oceanview retreat, nestled within the highly coveted Palms at Wailea. This nicely updated gro ...

    From $768 per night (USD)

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  • SPEND THE HOLIDAYS IN LUXURY AT ANDAZ 813 OCEAN VIEW PENTHOUSE 3Br\/4Ba for 8!
    From $4852 per night (USD)

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    SPEND THE HOLIDAYS IN LUXURY AT ANDAZ 813 OCEAN VIEW PENTHOUSE 3Br\/4Ba for 8!

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    8

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

    From $4852 per night (USD)

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  • Close to Everything, Stunning Palms at Wailea Condo, Full A\/C, Upper Floor
    From $651 per night (USD)

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    Close to Everything, Stunning Palms at Wailea Condo, Full A\/C, Upper Floor

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to Palms at Wailea 2304. Come to Wailea to enjoy the most beautiful beaches and best restaurants Maui has to off ...

    From $651 per night (USD)

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  • Luxurious 3 Bedroom Villa at Ho'olei! Perfect for Families! Ho'olei 55-2
    From $1787 per night (USD)

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    Luxurious 3 Bedroom Villa at Ho'olei! Perfect for Families! Ho'olei 55-2

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    8

    This property is hotel zoned, and not being affected by the recent proposed legislation. Relax and enjoy your Maui vaca ...

    From $1787 per night (USD)

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  • Amazing Ocean Views! Completely Redesigned and Refurnished! Wailea Ekolu 502
    From $613 per night (USD)

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    Amazing Ocean Views! Completely Redesigned and Refurnished! Wailea Ekolu 502

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Enjoy the fully remodeled kitchen, vaulted ceilings throughout, open floor plan, and STUNNING ocean views! All windows h ...

    From $613 per night (USD)

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  • Top Floor! Fantastic Ocean and Fairway Views! Grand Champions 74
    From $397 per night (USD)

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    Top Floor! Fantastic Ocean and Fairway Views! Grand Champions 74

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    VIEWS! VIEWS! VIEWS! Ocean and fairway views from this top floor unit. Wow! This unit has large living room, comfortable ...

    From $397 per night (USD)

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  • Fantastic Oceanfront unit on ground floor! PB 107
    From $1416 per night (USD)

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    Fantastic Oceanfront unit on ground floor! PB 107

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Experience true paradise and stunning ocean views from the lanai as you sip on your morning coffee! Stroll along the wor ...

    From $1416 per night (USD)

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  •  Exquisite Prime Beachfront Haven, Indulge in Tropical Luxury -Wailea Elua 1302
    From $1445 per night (USD)

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    Exquisite Prime Beachfront Haven, Indulge in Tropical Luxury -Wailea Elua 1302

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Experience the epitome of tropical luxury at Wailea Elua #1302. This exquisite beachfront haven is nestled within the co ...

    From $1445 per night (USD)

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  • Gorgeous Condo in Wailea Ekahi Village!
    From $668 per night (USD)

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    Gorgeous Condo in Wailea Ekahi Village!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Wailea Ekahi Village Resort is located on the world famous Keawakapu Beach. Low rise buildings built in clusters sprawl ...

    From $668 per night (USD)

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  • Wailea Ekahi 26B! Spacious with Garden Views!
    From $457 per night (USD)

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    Wailea Ekahi 26B! Spacious with Garden Views!

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Book 6 nights and get the 7th free or enjoy a complimentary mid-stay clean for 7+ nights. Stay 7+ nights and receive a $ ...

    From $457 per night (USD)

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  • Polo Beach 309! Private Corner Unit!
    From $1121 per night (USD)

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    Polo Beach 309! Private Corner Unit!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    *Book 5 nights and enjoy the 6th night free! Valid for new reservations from 8/6/24 for stays between 8/6/24 and 11/21/2 ...

    From $1121 per night (USD)

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  • New Listing! Elua 1603- Premier Views! Gorgeous Updates! Favorite Property!
    From $2350 per night (USD)

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    New Listing! Elua 1603- Premier Views! Gorgeous Updates! Favorite Property!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Elua Village #1603 boasts some of the best Ocean Views and is located on one of the most prestigious properties o ...

    From $2350 per night (USD)

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  • Wailea Ekolu 505, Ocean Views, New Furnishings
    From $522 per night (USD)

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    Wailea Ekolu 505, Ocean Views, New Furnishings

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Spectacular Ocean and Sunset Views!! A short walk to Wailea’s best beaches. Newly furnished and well appointed home will ...

    From $522 per night (USD)

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  • Wailea Point | 3203 | 30+ Night Luxury Stays
    From $730 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 $730 per night (USD)

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  • Luxurious Wailea Ocean Vistas
    From $1129 per night (USD)

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    Luxurious Wailea Ocean Vistas

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $1129 per night (USD)

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  • Wailea Ekahi 4E, Bordering Private Tropical Greenbelt, Split AC and Beautiful!
    From $1112 per night (USD)

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    Wailea Ekahi 4E, Bordering Private Tropical Greenbelt, Split AC and Beautiful!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The main pool, pool deck, and beach gate will be closed from June 3, 2024 to June 14, 2024 to clean, restore, and re-sea ...

    From $1112 per night (USD)

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  • Elua 1310 Ocean Front Condo - Family Managed - 50 Steps to the Beachfront\/Walk!
    From $1208 per night (USD)

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    Elua 1310 Ocean Front Condo - Family Managed - 50 Steps to the Beachfront\/Walk!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Only 11 reviews? Pshaw....! We have 35+ 5-star reviews on our property in Ekahi and 500+ consecutive 5-star customer r ...

    From $1208 per night (USD)

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  • Panoramic Views - Fourth Row Ho'olei - One of a Kind 112-4
    From $2071 per night (USD)

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

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    8

    Newly Remodeled in 2023! Come relax and enjoy the spectacular ocean and island views in this rare three Bedroom Condo wi ...

    From $2071 per night (USD)

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  • Remodelled 3 Bdrm Grand Champions Villa with Full Ocean View and New Central A\/C
    From $700 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:
    4
    Sleeps:
    7

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

    From $700 per night (USD)

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  • This is the one! Impressive Ekahi 1 Bd+2Ba Condominium 20G
    From $454 per night (USD)

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    This is the one! Impressive Ekahi 1 Bd+2Ba Condominium 20G

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    At Wailea Ekahi Village 20G, you and your guests will enjoy premier accommodations, furnishings and holiday experiences ...

    From $454 per night (USD)

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  • Grand Champions 27 | Golf Course, Haleakala Views
    From $590 per night (USD)

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    Grand Champions 27 | Golf Course, Haleakala Views

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Embark on a Hawaiian getaway like no other at Grand Champions 27 in sunny Wailea! This exquisite two-bedroom, two-bathro ...

    From $590 per night (USD)

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  • Wailea Ekahi 48C ~ 1 Bedroom 2 Bath Wailea Condo!
    From $443 per night (USD)

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

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $443 per night (USD)

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  • Wailea Ekahi 46F Spacious 2 bedroom 2 Bath Condo in Wailea - In upper village
    From $558 per night (USD)

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    Wailea Ekahi 46F Spacious 2 bedroom 2 Bath Condo in Wailea - In upper village

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

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

    From $558 per night (USD)

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  • Stunning Remodel, Beautiful Views, Great Quiet Location Close to Pool\/Beach! 28A
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    Stunning Remodel, Beautiful Views, Great Quiet Location Close to Pool\/Beach! 28A

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Wailea Ekahi 28A is a stunning, spacious, fully renovated ground-floor two-bedroom/two-bath vacation condo in the presti ...

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  • Polo Beach Club  |  608
    From $907 per night (USD)

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    Polo Beach Club | 608

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Polo Beach Club 608 is an exquisite two-bedroom, two-bath residence designed to accommodate up to six guests. With its i ...

    From $907 per night (USD)

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  • Fantastically Remodeled Condo with Huge Ocean Views
    From $382 per night (USD)

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    Fantastically Remodeled Condo with Huge Ocean Views

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $382 per night (USD)

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  • PAW 1306 Whale Watch Winter Getaway Remodeled 2BD Wailea Condo w Pool Ocean View
    From $764 per night (USD)

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    PAW 1306 Whale Watch Winter Getaway Remodeled 2BD Wailea Condo w Pool Ocean View

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    FREE daily activities included with your stay value up to $956! Complimentary admission, every day of your stay*: Lu’au, ...

    From $764 per night (USD)

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  • Wailea Ekahi Village | 40C
    From $490 per night (USD)

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    Wailea Ekahi Village | 40C

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Ekahi Village 40C was fully renovated in the summer of 2021. Open the windows or lanai doors and let the Maui bre ...

    From $490 per night (USD)

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  • Unique Private Ocean View House With Pool - Walking Distance To Wailea Resorts
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    Unique Private Ocean View House With Pool - Walking Distance To Wailea Resorts

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    9

    Wailea Freedom House is pure and simple elegance in an unmatched location backing onto the Wailea Blue Golf Course. This ...

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  • OCEAN BLISS  Oceanfront Private Home
    From $5362 per night (USD)

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    OCEAN BLISS Oceanfront Private Home

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    State of Hawaii Transient Accommodations Tax License #TA-053-364-5312-03 County of Maui Short-Term Rental License #Hotel ...

    From $5362 per night (USD)

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  • Stunning Remodel, Fantastic Lower Village Location, 1 Minute to Pool & Beach! 6C
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    Stunning Remodel, Fantastic Lower Village Location, 1 Minute to Pool & Beach! 6C

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    3

    Wailea Ekahi 6C is a stunning, spacious, fully renovated ground-floor one-bedroom/two-bathroom vacation condo in the pre ...

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