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  1. $767 to $2,781/night

    Wailea Beach Villa H102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  3. $288 to $833/night

    Sugar Beach Resort 235

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  5. $2,532 to $9,183/night

    Andaz Villa 810

    3 Bedrooms, 4 Bathrooms, Sleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  7. $633 to $1,242/night

    Boston Commons Penthouse

    5 Bedrooms, 4 Bathrooms, Sleeps 14
    3 nights minstay
    Pool
    FREE CANCELLATION
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  9. $520 to $3,339/night

    Wailea Beach Villa I204

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  11. $208 to $672/night

    Big Island Keauhou Surf & Racquet 181

    2 Bedrooms, 2 Bathrooms, Sleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  13. $222 to $1,223/night

    Admiral's Quarters 402

    3 Bedrooms, 3 Bathrooms, Sleeps 10
    7 nights minstay
    Hot Tub
    FREE CANCELLATION
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  15. $193 to $1,051/night

    Sea Chase 505C

    3 Bedrooms, 2 Bathrooms, Sleeps 8
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
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  17. $289 to $872/night

    Sugar Beach Resort 113

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  19. $2,811 to $9,598/night

    Wailea Beach Villa B202

    3 Bedrooms, 3.5 Bathrooms, Sleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  21. $1,096 to $4,770/night

    Wailea Beach Villa I503

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  23. $214 to $580/night

    Sugar Beach Resort PH8

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  25. $1,212 to $4,244/night

    Wailea Elua 1603

    2 Bedrooms, 2 Bathrooms, Sleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  27. $1,154 to $4,666/night

    Wailea Beach Villa M312

    3 Bedrooms, 3 Bathrooms, Sleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  29. $520 to $1,924/night

    Wailea Elua 2303

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  31. $272 to $738/night

    Sugar Beach Resort 409

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  33. $449 to $1,167/night

    Breathtaking Beach Front House

    3 Bedrooms, 2.5 Bathrooms, Sleeps 6
    1 night minstay
    Hot Tub Pets OK
    FREE CANCELLATION
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  35. $3,035 to $10,816/night

    Wailea Beach Villa B102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  37. $491 to $1,893/night

    Tidal Wave- Big and Bold Bayfront Beauty! Perfect for th...

    6 Bedrooms, 4.5 Bathrooms, Sleeps 17
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  39. $808 to $2,781/night

    Wailea Beach Villa J106

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  41. $254 to $689/night

    Sugar Beach Resort 209

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  43. $300 to $794/night

    Sugar Beach Resort 328

    1 Bedroom, 1  Bathroom, Sleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  45. $1,038 to $3,624/night

    Wailea Beach Villa H202

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  46. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
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