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  1. $357 to $1,249/night

    Wailea Ekahi 40D

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  3. $2,811 to $9,598/night

    Wailea Beach Villa B202

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  5. $249 to $738/night

    Mahina Surf 111

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  7. $1,017 to $3,341/night

    Anahola Aloha Beach House

    4 BedroomsBathroomsSleeps 12
    3 nights minstay
    Hot Tub
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  9. $203 to $657/night

    Kahana Reef 217

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  11. $267 to $888/night

    Island Sands 600

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  13. $283 to $1,108/night

    Nohonani 102

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
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  15. $467 to $1,338/night

    My Waii Beach Cottage

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    FREE CANCELLATION
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  17. $403 to $1,289/night

    Kamaole Nalu 504

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  19. $260 to $1,035/night

    Wailea Ekahi 48E

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  21. $254 to $689/night

    Sugar Beach Resort 209

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  23. $318 to $1,056/night

    Wailea Ekahi 53D

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  25. $577 to $1,956/night

    Wailea Ekahi 48A

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  27. $458 to $1,475/night

    Royal Mauian 204

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  29. $198 to $562/night

    Kauai Plantation Hale Suites J2

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  31. $808 to $2,781/night

    Wailea Beach Villa J106

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  33. $214 to $580/night

    Sugar Beach Resort PH8

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  35. $520 to $3,339/night

    Wailea Beach Villa I204

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  37. $208 to $529/night

    Hale Ono Loa 411

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  39. $767 to $2,781/night

    Wailea Beach Villa H102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  41. $528 to $1,388/night

    Royal Mauian 206

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  43. $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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  45. $220 to $612/night

    Maui Kai 607

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  47. $203 to $668/night

    Hale Kai 115

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  49. $701 to $3,239/night

    Wailea Elua 2305

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  51. $272 to $738/night

    Sugar Beach Resort 409

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  53. $340 to $1,045/night

    Island Sands 306

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  55. $230 to $580/night

    Kahana Reef 305

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  57. $289 to $908/night

    Wailea Ekahi 36B

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  59. $353 to $1,271/night

    Kamaole Nalu 402

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
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  61. $469 to $1,671/night

    Wailea Ekahi 5E

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  63. $208 to $570/night

    Valley Isle 301

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  65. $243 to $670/night

    Kahana Reef 120

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  67. $1,038 to $3,624/night

    Wailea Beach Villa H202

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  69. $288 to $833/night

    Sugar Beach Resort 235

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  71. $329 to $808/night

    Kapalua Bay Villas 37G1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  73. $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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  75. $312 to $958/night

    Kamaole Nalu 103

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
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  77. $279 to $934/night

    Kauhale Makai 433

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  79. $300 to $1,163/night

    Wailea Ekahi 45A

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  81. $324 to $877/night

    Wailea Ekahi 47E

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  83. $278 to $875/night

    Waiohuli Beach Hale C211

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $289 to $917/night

    Wailea Ekahi 49F

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  87. $217 to $548/night

    Kauhale Makai 308

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $260 to $1,128/night

    Valley Isle 708

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $289 to $872/night

    Sugar Beach Resort 113

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $520 to $1,924/night

    Wailea Elua 2303

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  95. $230 to $540/night

    Kahana Reef 205

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  97. $1,846 to $5,684/night

    Halama Hale Private Home

    4 Bedrooms3.5 BathroomsSleeps 14
    2 nights minstay
    Pool
    FREE CANCELLATION
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $150 to $446/night

    Kauhale Makai 102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  101. $203 to $570/night

    Kahana Reef 315

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $521 to $1,818/night

    Sands Of Kahana PH 381 3Bd/3Ba OF

    3 BedroomsBathroomsSleeps 10
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $352 to $457/night

    Kaha Lani #222

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $390 to $815/night

    Sands of Kahana 282 2 Bedroom Condo

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $572 to $756/night

    Waipouli Beach Resort G-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $388 to $572/night

    Waipouli Beach Resort E-205

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $493 to $756/night

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $200 to $420/night

    Keauhou Kona Surf & Racquet Club #6-104

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pool
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $200 to $525/night

    Keauhou Kona Surf & Racquet Club #5-202

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $388 to $572/night

    Waipouli Beach Resort C-205

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $388 to $572/night

    Waipouli Beach Resort C-105

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $572 to $756/night

    Waipouli Beach Resort G-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $493 to $756/night

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $328 to $436/night

    Waipouli Beach Resort E-406

    1 Bedroom1.5  BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations