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  1. $2,733 to $10,705/night

    Wailea Beach Villa B102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  3. $2,670 to $9,559/night

    Wailea Beach Villa B202

    3 Bedrooms, 3.5 Bathrooms, Sleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  5. $1,038 to $4,024/night

    Ho'olei 112-5

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  7. $1,038 to $4,656/night

    Ho'olei 17-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  9. $981 to $4,028/night

    Ho'olei 21-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  11. $980 to $4,965/night

    Ho'olei 17-1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  13. $923 to $4,134/night

    Ho'olei 24-4

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  15. $866 to $3,406/night

    Ho'olei 24-6

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  17. $831 to $3,388/night

    Ho'olei 55-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  19. $831 to $3,771/night

    Ho'olei 24-1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  21. $767 to $2,768/night

    Wailea Beach Villa H102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  23. $722 to $3,501/night

    Ho'olei 24-2

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  25. $328 to $467/night

    Regency at Poipu Kai #914

    2 Bedrooms, 2 Bathrooms, Sleeps 4
    3 nights minstay
    Pool Hot Tub
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  27. $320 to $436/night

    Waipouli Beach Resort E-406

    1 Bedroom, 1.5  Bathroom, Sleeps 4
    2 nights minstay
    Pool Hot Tub
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  29. $198 to $624/night

    Kamaole Sands 6-102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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