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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. $2,653 to $9,501/night

    Wailea Beach Villa B202

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  5. $2,423 to $9,090/night

    Andaz Villa 810

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  7. $1,662 to $5,684/night

    Halama Hale Private Home

    4 Bedrooms3.5 BathroomsSleeps 14
    2 nights minstay
    Pool
    FREE CANCELLATION
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  9. $1,141 to $4,247/night

    The Cove Hale

    4 BedroomsBathroomsSleeps 16
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  11. $1,101 to $4,619/night

    Wailea Beach Villa M312

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  13. $1,098 to $3,736/night

    Big Island Hale Kaheka 6592

    1 Bedroom2.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  15. $1,091 to $4,200/night

    Wailea Elua 1603

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  17. $1,083 to $1,459/night

    Luxury Makalae Home close to Water Activities

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
  18. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  19. $1,083 to $1,459/night

    Makalae

    5 BedroomsBathroomsSleeps 10
    3 nights minstay
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  21. $1,017 to $3,487/night

    Anahola Aloha Beach House

    4 BedroomsBathroomsSleeps 12
    3 nights minstay
    Hot Tub
  22. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  23. $1,014 to $4,254/night

    Big Island Hualalai 133C

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  25. $987 to $4,721/night

    Wailea Beach Villa I503

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  27. $980 to $4,934/night

    Ho'olei 17-1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  29. $935 to $4,001/night

    Ho'olei 112-5

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  31. $935 to $3,587/night

    Wailea Beach Villa H202

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  33. $935 to $4,628/night

    Ho'olei 17-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  35. $896 to $1,456/night

    HOKUEA HALE

    3 Bedrooms2.5 BathroomsSleeps 10
    3 nights minstay
    Hot Tub
  36. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  37. $890 to $2,779/night

    Honua Kai Konea 250

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  39. $889 to $4,181/night

    Ho'olei 39-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  41. $883 to $4,003/night

    Ho'olei 21-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  43. $858 to $2,340/night

    Big Island Private Home Alii Drive 6596

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $831 to $3,388/night

    Ho'olei 55-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  47. $831 to $4,108/night

    Ho'olei 24-4

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $831 to $2,531/night

    Polo Beach Club 106

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  50. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  51. $831 to $3,771/night

    Ho'olei 24-1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $831 to $2,294/night

    Big Island Holua Kai 7061

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  55. $830 to $2,950/night

    Maui Dolphin House

    4 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $829 to $3,694/night

    Ho'olei 55-2

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $780 to $3,386/night

    Ho'olei 24-6

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $778 to $3,341/night

    Ho'olei 12-4

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  63. $760 to $1,108/night

    Pu'uwai Hale

    4 Bedrooms4.5 BathroomsSleeps 8
    3 nights minstay
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  65. $754 to $1,420/night

    Kapalua Ridge Villas-#323

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $727 to $2,751/night

    Wailea Beach Villa J106

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $722 to $3,501/night

    Ho'olei 24-2

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $691 to $2,751/night

    Wailea Beach Villa H102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $655 to $808/night

    Molokama Vacation Home in Hanalei Bay Near Beach

    4 BedroomsBathroomsSleeps 8
    3 nights minstay
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $650 to $2,276/night

    Noelani 306

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $644 to $1,966/night

    Wailea Elua 2109

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $631 to $3,203/night

    Wailea Elua 2305

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $592 to $1,950/night

    Noelani 307

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $590 to $2,763/night

    Polo Beach Club 107

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  85. $555 to $801/night

    Ainamalu at Waikoloa Beach Resort

    3 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    FREE CANCELLATION
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $547 to $748/night

    Mauna Lani Golf Villas K5

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $545 to $780/night

    Villages At Mauna Lani 621

    3 Bedrooms3.5 BathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $545 to $1,284/night

    Wai'ula'ula D201

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $543 to $2,119/night

    Kauai Poipu Kapili 51

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
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  95. $520 to $1,508/night

    Mana Kai #403

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $520 to $3,304/night

    Wailea Beach Villa I204

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $520 to $1,466/night

    Big Island Holua Kai 111

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $520 to $1,935/night

    Wailea Ekahi 48A

    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. $498 to $1,672/night

    Mana Kai #705

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $494 to $1,269/night

    Big Island Holua Kai 7066

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $475 to $1,388/night

    Royal Mauian 206

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $469 to $627/night

    Kauai Tree House

    3 BedroomsBathroomsSleeps 7
    2 nights minstay
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $468 to $1,628/night

    Mana Kai #614

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
    FREE CANCELLATION
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $468 to $1,903/night

    Wailea Elua 2303

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $467 to $677/night

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $467 to $677/night

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $467 to $1,260/night

    Mana Kai #203

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $467 to $1,329/night

    Mana Kai #815

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $467 to $677/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. $467 to $677/night

    Waipouli Beach Resort G-404

    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. $461 to $1,864/night

    Maui Hill 66

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $450 to $1,576/night

    Kauai Kiahuna Plantation #64

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $442 to $1,439/night

    Royal Mauian 512

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $437 to $1,484/night

    Mana Kai #805

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $433 to $1,483/night

    Wailea Ekahi 39E

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $430 to $1,907/night

    Wailea Ekahi 26A

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $421 to $1,653/night

    Wailea Ekahi 5E

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $421 to $1,712/night

    Big Island Kolea 11C

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $420 to $1,338/night

    My Waii Beach Cottage

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $416 to $1,420/night

    Kapalua Ridge Villas-#2212

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $416 to $1,406/night

    Kauai Sunset Hale in Poi'pu

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool
    FREE CANCELLATION
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $416 to $716/night

    Fairway Villas Waikoloa F6

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $412 to $1,475/night

    Royal Mauian 204

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $410 to $486/night

    Turtle Bay Aloha Nui Loa

    1 BedroomBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $410 to $475/night

    Turtle Bay Hale Lani

    1 Bedroom1.5  BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $404 to $1,714/night

    Mana Kai #814

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $395 to $572/night

    Regency at Poipu Kai #924

    3 BedroomsBathroomsSleeps 7
    3 nights minstay
    Pool Hot Tub
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $395 to $572/night

    Regency at Poipu Kai #924

    3 BedroomsBathroomsSleeps 7
    3 nights minstay
    Pool Hot Tub
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $391 to $1,269/night

    Palms at Wailea 2104

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $388 to $572/night

    Puu Poa #305

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $382 to $1,332/night

    Big Island Kona Bali Kai 301

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $380 to $1,033/night

    Kapalua Golf Villas 27P7

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $370 to $1,236/night

    Wailea Ekolu 1603

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $370 to $1,196/night

    Kauai Pili Mai 14J

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $364 to $1,369/night

    Mana Kai #508

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $364 to $1,151/night

    Mana Kai #303

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $364 to $1,109/night

    Mana Kai #412

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $364 to $1,047/night

    Maalaea Surf G8

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $364 to $1,120/night

    Maui Sunset B217

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $363 to $1,289/night

    Kamaole Nalu 504

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $362 to $424/night

    Hamakua Pukana La Hale

    3 BedroomsBathroomsSleeps 7
    3 nights minstay
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $357 to $1,593/night

    Wailea Ekahi 34B

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $352 to $457/night

    Kaha Lani #222

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $352 to $457/night

    Nihilani 22C

    3 Bedrooms2.5 BathroomsSleeps 7
    3 nights minstay
    Pool Hot Tub
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $352 to $541/night

    Waipouli Beach Resort E-205

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $352 to $737/night

    Waikoloa Beach Villas J32

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $352 to $572/night

    Waipouli Beach Resort C-105

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  200. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations