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Results: 913 Rentals

  • Wailea Ekahi Village | 9A
    From $899 per night (USD)

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    Wailea Ekahi Village | 9A

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to Wailea Ekahi 9A, a charming vacation rental nestled in the heart of Wailea. This meticulously maintained one- ...

    From $899 per night (USD)

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  • Wailea Elua Village | 1001
    From $1194 per night (USD)

    Expedia

    Wailea Elua Village | 1001

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Elua Village #1001 is a stunning oceanfront sanctuary that has recently undergone a complete transformation. F ...

    From $1194 per night (USD)

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    Details
  • Wailea Ekahi Village | 4D
    From $826 per night (USD)

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    Wailea Ekahi Village | 4D

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Wailea Ekahi 4D is a charming studio vacation rental perfect for the couple or solo traveler. This second-floor unit off ...

    From $826 per night (USD)

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  • Wailea Elua Village | 1511
    From $604 per night (USD)

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    Wailea Elua Village | 1511

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Wailea Elua Village 1511 is a premier vacation rental nestled in the heart of Wailea, offering a perfect blend of luxury ...

    From $604 per night (USD)

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    Details
  • Wailea Elua Village | 804
    From $1392 per night (USD)

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    Wailea Elua Village | 804

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    The Wailea Elua 804 vacation rental is a true gem nestled within the picturesque Wailea resort community on the island o ...

    From $1392 per night (USD)

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  • Wailea Elua Village | 1203
    From $749 per night (USD)

    Expedia

    Wailea Elua Village | 1203

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Wailea Elua 1203 is a stunning one-bedroom, one-bathroom oceanfront vacation rental located on the ground floor of the p ...

    From $749 per night (USD)

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  • Wailea Ekahi Village | 12B
    From $832 per night (USD)

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    Wailea Ekahi Village | 12B

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Wailea Ekahi Village 12B is a beautiful vacation rental that underwent a complete update in March 2021. Interior designe ...

    From $832 per night (USD)

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  • Wailea Ekahi Village | 11C
    From $1041 per night (USD)

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    Wailea Ekahi Village | 11C

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Wailea Ekahi 11C is an ideal Hawaiian retreat for friends or families traveling together. Each of the two bedrooms in t ...

    From $1041 per night (USD)

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    Details
  • Wailea Elua Village | 2402
    From $662 per night (USD)

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    Wailea Elua Village | 2402

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Wailea Elua Village 2402 is an exquisite ocean-view second-floor condo located in the prestigious Wailea area of Maui. T ...

    From $662 per night (USD)

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  • Wailea Elua Village | 705
    From $788 per night (USD)

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    Wailea Elua Village | 705

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Wailea Elua 705 is an exquisite vacation rental located on the stunning shores of Maui. This newly renovated, two-bedroo ...

    From $788 per night (USD)

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  • Wailea Ekahi Village | 15D
    From $899 per night (USD)

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    Wailea Ekahi Village | 15D

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to Wailea Ekahi 15D, a stunning one-bedroom, one-bathroom vacation rental nestled in the heart of Wailea. This s ...

    From $899 per night (USD)

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  • Wailea Elua Village | 1202
    From $645 per night (USD)

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    Wailea Elua Village | 1202

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Wailea Elua 1202 is a stunning vacation rental property that offers visitors a truly luxurious and unforgettable experie ...

    From $645 per night (USD)

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  • Wailea Elua Village | 2005
    From $858 per night (USD)

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    Wailea Elua Village | 2005

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Wailea Elua Village 2005 is a stunning two-bedroom, two-bathroom vacation rental located in the desirable Wailea region ...

    From $858 per night (USD)

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  • Wailea Elua Village | 1510
    From $859 per night (USD)

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    Wailea Elua Village | 1510

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Elua 1510 is a charming two-bedroom, two-bathroom vacation rental located in the premier Maui vacation destinatio ...

    From $859 per night (USD)

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    Details
  • Wailea Ekahi Village | 3B
    From $823 per night (USD)

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    Wailea Ekahi Village | 3B

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Nestled among the lush, tropical landscape, this studio is a perfect place to escape the hustle and bustle. Bring along ...

    From $823 per night (USD)

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  • Wailea Elua Village | 208
    From $668 per night (USD)

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    Wailea Elua Village | 208

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to Wailea Elua 208, where paradise meets luxury! This stunning one-bedroom ocean view vacation rental is the per ...

    From $668 per night (USD)

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  • Wailea Ekahi Village | 8D
    From $899 per night (USD)

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    Wailea Ekahi Village | 8D

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

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

    From $899 per night (USD)

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  • Wailea Ekahi Village | 4B
    From $826 per night (USD)

    Expedia

    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 $826 per night (USD)

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    Details
  • Wailea Ekahi Village | 19B
    From $1111 per night (USD)

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    Wailea Ekahi Village | 19B

    Bedrooms:
    2
    Bathrooms:
    2
    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 $1111 per night (USD)

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  • Wailea Elua Village | 2008
    From $645 per night (USD)

    Expedia

    Wailea Elua Village | 2008

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

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

    From $645 per night (USD)

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    Details
  • Wailea Ekahi Village | 3E
    From $899 per night (USD)

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    Wailea Ekahi Village | 3E

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

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

    From $899 per night (USD)

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  • Wailea Grand Champions | 97
    From $731 per night (USD)

    Expedia

    Wailea Grand Champions | 97

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

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

    From $731 per night (USD)

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    Details
  • Wailea Ekahi Village | 29D
    From $970 per night (USD)

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    Wailea Ekahi Village | 29D

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

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

    From $970 per night (USD)

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  • Wailea Grand Champions | 104
    From $735 per night (USD)

    Expedia

    Wailea Grand Champions | 104

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

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

    From $735 per night (USD)

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  • Wailea Grand Champions | 140
    From $900 per night (USD)

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    Wailea Grand Champions | 140

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

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

    From $900 per night (USD)

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  • Wailea Ekahi Village | 44B
    From $823 per night (USD)

    Expedia

    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 $823 per night (USD)

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    Details
  • Wailea Ekahi Village | 22F
    From $1098 per night (USD)

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    Wailea Ekahi Village | 22F

    Bedrooms:
    2
    Bathrooms:
    2
    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 $1098 per night (USD)

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  • Wailea Grand Champions | 159
    From $1027 per night (USD)

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    Wailea Grand Champions | 159

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

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

    From $1027 per night (USD)

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  • Wailea Grand Champions | 116
    From $731 per night (USD)

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    Wailea Grand Champions | 116

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

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

    From $731 per night (USD)

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  • Wailea Ekahi Village | 25D
    From $899 per night (USD)

    Expedia

    Wailea Ekahi Village | 25D

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

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

    From $899 per night (USD)

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    Details
  • Wailea Grand Champions | 73
    From $731 per night (USD)

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    Wailea Grand Champions | 73

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

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

    From $731 per night (USD)

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  • Wailea Grand Champions | 121
    From $444 per night (USD)

    Expedia

    Wailea Grand Champions | 121

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

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

    From $444 per night (USD)

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    Details
  • Wailea Ekahi Village | 40F
    From $899 per night (USD)

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    Wailea Ekahi Village | 40F

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

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

    From $899 per night (USD)

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  • Wailea Grand Champions | 71
    From $906 per night (USD)

    Expedia

    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 $906 per night (USD)

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  • Wailea Grand Champions | 181
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    Wailea Grand Champions | 181

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

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

    Click For Pricing

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  • Wailea Grand Champions | 152
    From $731 per night (USD)

    Expedia

    Wailea Grand Champions | 152

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

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

    From $731 per night (USD)

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  • Wailea Beach Villas | PH502
    From $1390 per night (USD)

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    Wailea Beach Villas | PH502

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $1390 per night (USD)

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  • Wailea Beach Villas | PH201
    From $1475 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 $1475 per night (USD)

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    Details
  • Wailea Grand Champions | 31
    From $908 per night (USD)

    VRBO

    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 $908 per night (USD)

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  • Wailea Grand Champions | 95
    From $1027 per night (USD)

    Expedia

    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 $1027 per night (USD)

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    Details
  • Wailea Beach Villas | PH104
    From $1157 per night (USD)

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    Wailea Beach Villas | PH104

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

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

    From $1157 per night (USD)

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  • Wailea Grand Champions | 185
    From $900 per night (USD)

    Expedia

    Wailea Grand Champions | 185

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

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

    From $900 per night (USD)

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  • Wailea Beach Villas | PH411
    From $1502 per night (USD)

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    Wailea Beach Villas | PH411

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

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

    From $1502 per night (USD)

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  • Wailea Ekahi Village | 42C
    From $899 per night (USD)

    Expedia

    Wailea Ekahi Village | 42C

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

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

    From $899 per night (USD)

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  • Wailea Grand Champions | 111
    From $900 per night (USD)

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    Wailea Grand Champions | 111

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

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

    From $900 per night (USD)

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  • Wailea Ekahi Village | 35C
    From $899 per night (USD)

    Expedia

    Wailea Ekahi Village | 35C

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

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

    From $899 per night (USD)

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    Details
  • Wailea Ekahi Village | 34E
    From $952 per night (USD)

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    Wailea Ekahi Village | 34E

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

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

    From $952 per night (USD)

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  • Wailea Grand Champions | 183
    From $906 per night (USD)

    Expedia

    Wailea Grand Champions | 183

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

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

    From $906 per night (USD)

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  • Wailea Grand Champions | 177
    From $731 per night (USD)

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    Wailea Grand Champions | 177

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

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

    From $731 per night (USD)

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  • Wailea Beach Villas | PH207
    From $1243 per night (USD)

    Expedia

    Wailea Beach Villas | PH207

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Upon entering your Wailea Beach Villas PH207, you'll be captivated by the open floor plan, which seamlessly integrates a ...

    From $1243 per night (USD)

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    Details
  • Wailea Ekahi Village | 3C
    From $899 per night (USD)

    VRBO

    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 $899 per night (USD)

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  • Wailea Elua Village | 104
    From $664 per night (USD)

    Expedia

    Wailea Elua Village | 104

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

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

    From $664 per night (USD)

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    Details
  • Wailea Elua Village | 1607
    From $1478 per night (USD)

    VRBO

    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 $1478 per night (USD)

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  • Immaculate Wailea Point 3 Bedroom/3+ Bath Oceanview Condominium
    From $1560 per night (USD)

    Expedia

    Immaculate Wailea Point 3 Bedroom/3+ Bath Oceanview Condominium

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    6

    Please call or email us about the dates for your visit. You are welcome to island-hop or come and go as you please duri ...

    From $1560 per night (USD)

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    Details
  • FAMILY FUN & LUXURY ANDAZ PENTHOUSE OCEAN & SUNSET VIEWS FROM LANAI HOT TUB 3 Br/4 Ba for 8
    From $2589 per night (USD)

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    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 $2589 per night (USD)

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  • Wailea Ekahi Ocean View Studio!  AC included
    From $495 per night (USD)

    Expedia

    Wailea Ekahi Ocean View Studio! AC included

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Experience Island Elegance at Wailea Ekahi Village 15E Welcome to your serene retreat in the heart of Wailea! Unit 15E ...

    From $495 per night (USD)

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    Details
  • Luxurious Maui Living at Palms 203
    From $520 per night (USD)

    VRBO

    Luxurious Maui Living at Palms 203

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

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

    From $520 per night (USD)

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    Details
  • Wailea Ekahi Village | 23C
    From $931 per night (USD)

    Expedia

    Wailea Ekahi Village | 23C

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to Wailea Ekahi Village 23C. This residence was fully renovated in the fall of 2024 and features beautiful furni ...

    From $931 per night (USD)

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

    VRBO

    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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  • Wailea Ekolu 106 | Serene Views + Access to Pool!
    From $454 per night (USD)

    VRBO

    Wailea Ekolu 106 | Serene Views + Access to Pool!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

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

    From $454 per night (USD)

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  • Wailea Ekahi Studio #52-E Beautifully Renovated Studio on Keawakapu Beach
    From $373 per night (USD)

    VRBO

    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 $373 per night (USD)

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  • Majestic Golf Course & Sweeping Ocean Vistas at Wailea Ekolu 312
    From $370 per night (USD)

    Expedia

    Majestic Golf Course & Sweeping Ocean Vistas at Wailea Ekolu 312

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Wailea Ekolu #312 – Unforgettable Ocean Views & Island Elegance Find your private slice of paradise at Wailea Ekolu #312 ...

    From $370 per night (USD)

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  • Wailea Ekahi Village | 51D
    From $1098 per night (USD)

    VRBO

    Wailea Ekahi Village | 51D

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Wailea Ekahi Village tropical vacation condos are situated above Maui's beautiful Keawakapu Beach and close to all the t ...

    From $1098 per night (USD)

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  • New! Palms 702 - Romantic Retreat - Split AC in Bedroom - Open-Air Living Area
    From $249 per night (USD)

    Expedia

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

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Discover the perfect Maui escape at Palms at Wailea 702, a beautifully updated 1-bedroom, 2-bath luxury vacation rental ...

    From $249 per night (USD)

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  • Palms at Wailea Villa 806 Ocean View.
    From $603 per night (USD)

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    Palms at Wailea Villa 806 Ocean View.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

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

    From $603 per night (USD)

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  • Gorgeous condo in a beachfront Wailea resort
    From $354 per night (USD)

    Expedia

    Gorgeous condo in a beachfront Wailea resort

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Wailea Ekahi 24B is a 1-bedroom, 2-bathroom condo that offers a split A/C system, a private washer/dryer, and easy acces ...

    From $354 per night (USD)

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  • Wailea Elua 702 - Beautifully Renovated, Stunning Ocean Views, Central AC, Wi-Fi
    From $662 per night (USD)

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

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

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

    From $662 per night (USD)

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  • Wailea Beach Villas | PH105
    From $1594 per night (USD)

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    Wailea Beach Villas | PH105

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

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

    From $1594 per night (USD)

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  • Wailea Ekahi Village | 35D
    From $596 per night (USD)

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    Wailea Ekahi Village | 35D

    Bedrooms:
    1
    Bathrooms:
    1
    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 $596 per night (USD)

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  • Cozy 1-bedroom condo with AC, WiFi in lovely Wailea-Makena
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    Cozy 1-bedroom condo with AC, WiFi in lovely Wailea-Makena

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    This enchanting condo in Wailea-Makena is the perfect home base for your trip. With 1 bedroom featuring a cozy king bed ...

    Click For Pricing

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  • Oceanview Paradise: Tropical Retreat in Wailea
    From $796 per night (USD)

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    Oceanview Paradise: Tropical Retreat in Wailea

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Welcome to our beautiful, elegantly remodeled 2-bedroom, 2-bathroom condo in the prestigious Wailea Grand Champions Vill ...

    From $796 per night (USD)

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  • Summer Sale! - Wailea Ekolu 403, Stunning Ocean Views, Split AC! - New Listing!
    From $330 per night (USD)

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    Summer Sale! - Wailea Ekolu 403, Stunning Ocean Views, Split AC! - New Listing!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to Wailea Ekolu 403, a stunning Maui vacation rental offering breathtaking ocean views, luxurious comfort, and a ...

    From $330 per night (USD)

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  • Wailea Beach Villas | PH404
    From $1375 per night (USD)

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    Wailea Beach Villas | PH404

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Wailea Beach Villas Penthouse 404 is a stunning two-bedroom plus den, two-bathroom ocean view residence offering over 1, ...

    From $1375 per night (USD)

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  • Walk to white sandy beaches - Palms 501
    From $429 per night (USD)

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    Walk to white sandy beaches - Palms 501

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This beautiful, tropical two-bedroom/two-bath condo is just a short 5-minute walk from the world-famous Keawakapu Beach! ...

    From $429 per night (USD)

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  • NEW! KBM Resorts | Ocean Views | FREE CAR | Wailea Ekahi | 1-Bedroom Condo with Luxury Amenities! WKV-45C
    From $607 per night (USD)

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    NEW! KBM Resorts | Ocean Views | FREE CAR | Wailea Ekahi | 1-Bedroom Condo with Luxury Amenities! WKV-45C

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    NEW! Recently updated Suite | Wailea Ekahi | Beachfront Resort | AC | Resort amenities including a beachfront pool-perfe ...

    From $607 per night (USD)

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  • Grand Champions Two Bedrooms - Garden View by Coldwell Banker Island Vacations
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    Grand Champions Two Bedrooms - Garden View by Coldwell Banker Island Vacations

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    <p>Nestled in Kihei, this 2-bedroom condo brings it all within your reach. Fans of nature and the outdoors will love bei ...

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  • Palms At Wailea 203 2 Bedroom Condo
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    Palms At Wailea 203 2 Bedroom Condo

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    1

    <p>Located in Kihei, this 2-bedroom condo lets you experience it all. Fans of nature and the outdoors will love being 15 ...

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  • Wailea Ekahi, #3d Condo
    Click For Pricing

    Expedia

    Wailea Ekahi, #3d Condo

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    1

    <p>Nestled in Kihei, this 1-bedroom condo brings it all within your reach. Fans of nature and the outdoors will love bei ...

    Click For Pricing

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  • Wailea Ekolu 104 2 Bedroom Condo
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    Wailea Ekolu 104 2 Bedroom Condo

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    1

    <p>Located in Kihei, this 1-bedroom condo lets you experience it all. Fans of nature and the outdoors will love being 12 ...

    Click For Pricing

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  • Elua 1603: Premier Views, Exquisite Updates!
    From $1490 per night (USD)

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    Elua 1603: Premier Views, Exquisite Updates!

    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 $1490 per night (USD)

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

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    <p>Nestled in Kihei, this 2-bedroom condo brings it all within your reach. Fans of nature and the outdoors will love bei ...

    Click For Pricing

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  • Polo Beach Club Two Bedrooms - Ground Floor by Coldwell Banker Island Vacations
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    Polo Beach Club Two Bedrooms - Ground Floor by Coldwell Banker Island Vacations

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    2

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

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  • Wailea Ekolu 505 ~ Big Ocean Views ~ New Furnishings
    From $433 per night (USD)

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    Wailea Ekolu 505 ~ Big Ocean Views ~ New Furnishings

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

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

    From $433 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 Ekolu One Bedrooms by Coldwell Banker Island Vacations
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    Wailea Ekolu One Bedrooms by Coldwell Banker Island Vacations

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    <p>Nestled in Kihei, this 1-bedroom condo brings it all within your reach. Fans of nature and the outdoors will love bei ...

    Click For Pricing

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  • Wailea Ekolu Two Bedrooms by Coldwell Banker Island Vacations
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    Wailea Ekolu Two Bedrooms by Coldwell Banker Island Vacations

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    <p>Nestled in Kihei, this 2-bedroom condo brings it all within your reach. Fans of nature and the outdoors will love bei ...

    Click For Pricing

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  • Grand Champions One Bedrooms by Coldwell Banker Island Vacations
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    Grand Champions One Bedrooms by Coldwell Banker Island Vacations

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    <p>Close to sailing, cycling, and more, this smoke-free condo brings it all within reach. Shops at Wailea is an easy 12- ...

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  • Wailea Elua by Coldwell Banker Island Vacations
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    Wailea Elua by Coldwell Banker Island Vacations

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    <p>Located in Kihei, this 2-bedroom condo lets you experience it all. Fans of nature and the outdoors will love being 15 ...

    Click For Pricing

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  • Grand Champions Three Bedrooms by Coldwell Banker Island Vacations
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    Grand Champions Three Bedrooms by Coldwell Banker Island Vacations

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    <p>Nestled in Kihei, this 3-bedroom condo brings it all within your reach. Fans of nature and the outdoors will love bei ...

    Click For Pricing

    Expedia

    Details
  • Wailea Beach Villas by Coldwell Banker Island Vacations
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    Wailea Beach Villas by Coldwell Banker Island Vacations

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    <p>Located in Kihei, this 2-bedroom condo lets you experience it all. Fans of nature and the outdoors will love being 3 ...

    Click For Pricing

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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>Located in Kihei, this 2-bedroom condo lets you experience it all. Fans of nature and the outdoors will love being 12 ...

    Click For Pricing

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  • Palms at Wailea Two Bedrooms - Partial Ocean View by Coldwell Banker Island Vacations
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    Palms at Wailea Two Bedrooms - Partial Ocean View by Coldwell Banker Island Vacations

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    <p>A short distance from sailing, cycling, and more, this smoke-free condo lets you experience it all. Keawakapu Beach N ...

    Click For Pricing

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  • Ho'olei Ocean View by Coldwell Banker Island Vacations
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    Ho'olei Ocean View by Coldwell Banker Island Vacations

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    <p>Located in Kihei, this 3-bedroom vacation home lets you experience it all. Fans of nature and the outdoors will love ...

    Click For Pricing

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    Details
  • Grand Champions Two Bedrooms - Ocean View by Coldwell Banker Island Vacations
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    Grand Champions Two Bedrooms - Ocean View by Coldwell Banker Island Vacations

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    <p>Nestled in Kihei, this 2-bedroom condo brings it all within your reach. Fans of nature and the outdoors will love bei ...

    Click For Pricing

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  • Gorgeous Beachfront Condo in Wailea with Private Lanai
    From $410 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 $410 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>Located in Kihei, this 3-bedroom villa lets you experience it all. Fans of nature and the outdoors will love being 10 ...

    Click For Pricing

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  • Wailea Ekahi Village | 40C
    From $550 per night (USD)

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    Wailea Ekahi Village | 40C

    Bedrooms:
    1
    Bathrooms:
    1
    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 $550 per night (USD)

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  • PAW 1306 Whale Watch at Remodeled 2BD Wailea Condo w Pool Ocean View
    From $500 per night (USD)

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

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

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

    From $500 per night (USD)

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  • Fantastically Remodeled Condo with Huge Ocean Views
    From $401 per night (USD)

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    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 $401 per night (USD)

    Expedia

    Details