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  1. $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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  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. $2,532 to $9,184/night

    Andaz Villa 810

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  7. $1,604 to $2,164/night

    Moloa'a Bay Villa & Cottage

    5 BedroomsBathroomsSleeps 11
    3 nights minstay
  8. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  9. $1,604 to $2,164/night

    Moloa'a Bay Villa & Cottage

    5 BedroomsBathroomsSleeps 11
    3 nights minstay
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  11. $1,220 to $3,698/night

    Big Island Hale Kaheka 6592

    1 Bedroom2.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  13. $1,126 to $4,204/night

    Big Island Hualalai 133C

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  15. $1,083 to $1,459/night

    Luxury Makalae Home close to Water Activities

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
  16. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  17. $1,083 to $1,459/night

    Makalae

    5 BedroomsBathroomsSleeps 10
    3 nights minstay
  18. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  19. $1,038 to $4,041/night

    Ho'olei 112-5

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  20. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  21. $1,038 to $4,675/night

    Ho'olei 17-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  23. $981 to $4,044/night

    Ho'olei 21-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  25. $980 to $4,985/night

    Ho'olei 17-1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  27. $923 to $4,151/night

    Ho'olei 24-4

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  28. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  29. $923 to $3,432/night

    Ho'olei 55-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  30. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  31. $923 to $3,823/night

    Ho'olei 24-1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  33. $923 to $2,260/night

    Big Island Holua Kai 7061

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  35. $866 to $3,600/night

    Ho'olei 24-6

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  37. $844 to $1,108/night

    Pu'uwai Hale

    4 Bedrooms4.5 BathroomsSleeps 8
    3 nights minstay
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $802 to $3,535/night

    Ho'olei 24-2

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  40. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  41. $767 to $2,779/night

    Wailea Beach Villa H102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  43. $763 to $1,783/night

    Hale Nanea

    1 Bedroom BathroomSleeps 2
    2 nights minstay
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $735 to $1,575/night

    Holua House#28

    3 Bedrooms3.5 BathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  46. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  47. $725 to $1,260/night

    Kona Bubbles

    4 Bedrooms4.5 BathroomsSleeps 8
    3 nights minstay
    Pool
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $701 to $3,239/night

    Wailea Elua 2305

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  50. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  51. $668 to $2,499/night

    Makena Surf B305

    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. $606 to $2,149/night

    Makena Surf A204

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  54. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  55. $555 to $801/night

    Ainamalu at Waikoloa Beach Resort

    3 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    FREE CANCELLATION
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $547 to $1,605/night

    Kauai Villas at Poipu Kai E211

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $545 to $1,284/night

    Wai'ula'ula D201

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $523 to $780/night

    Villages At Mauna Lani 621

    3 Bedrooms3.5 BathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $493 to $756/night

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $493 to $756/night

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $485 to $1,560/night

    Mana Kai #805

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $469 to $1,671/night

    Wailea Ekahi 5E

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $466 to $1,568/night

    Kauai Kiahuna Plantation #64

    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. $458 to $1,475/night

    Royal Mauian 204

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  75. $448 to $1,970/night

    Waikiki Beach Tower 1104

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $439 to $1,146/night

    Big Island White Sands Village 301

    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. $421 to $497/night

    Turtle Bay Hanalei

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $414 to $1,186/night

    Palms at Wailea 206

    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. $414 to $1,186/night

    Palms at Wailea 303

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $404 to $1,058/night

    Mana Kai #412

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $396 to $1,609/night

    Wailea Ekahi 34B

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $395 to $572/night

    Regency at Poipu Kai #924

    3 BedroomsBathroomsSleeps 7
    3 nights minstay
    Pool Hot Tub
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $395 to $572/night

    Regency at Poipu Kai #924

    3 BedroomsBathroomsSleeps 7
    3 nights minstay
    Pool Hot Tub
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $388 to $572/night

    Waipouli Beach Resort C-105

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $384 to $716/night

    Fairway Villas Waikoloa F6

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $373 to $428/night

    Luxurious Penthouse w panoramic ocean views

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $364 to $1,848/night

    Big Island Fairways at Mauna Lani 1705

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $362 to $424/night

    Hamakua Pukana La Hale

    3 BedroomsBathroomsSleeps 7
    3 nights minstay
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $346 to $1,030/night

    Kauai Regency at Poipu Kai #313

    2 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $346 to $1,269/night

    Kauai Aliomanu Sunrise Hale

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $345 to $1,273/night

    Grand Champions 137

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $341 to $737/night

    Waikoloa Beach Villas J32

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $328 to $436/night

    Waipouli Beach Resort E-406

    1 Bedroom1.5  BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $328 to $467/night

    Regency at Poipu Kai #914

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $320 to $427/night

    Waikoloa Beach Villas E33

    2 BedroomsBathroomsSleeps 5
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $320 to $459/night

    Waikoloa Beach Villas H32

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $312 to $1,074/night

    Luana Kai D305

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $306 to $1,239/night

    Wailea Ekolu 904

    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. $305 to $716/night

    Hale Ki'i Maka Manu

    4 BedroomsBathroomsSleeps 10
    3 nights minstay
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $304 to $1,249/night

    Wailea Ekolu 1507

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $301 to $1,144/night

    Maui Sunset B317

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $299 to $425/night

    Plantations at Princeville #521

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $299 to $438/night

    Colony Villas at Waikoloa Beach Resort #2204

    2 Bedrooms2.5 BathroomsSleeps 5
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $299 to $425/night

    Plantations at Princeville #521

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $299 to $630/night

    Fairways at Mauna Lani #1703

    2 Bedrooms2.5 BathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $294 to $350/night

    Hale Hamakua

    4 BedroomsBathroomsSleeps 9
    2 nights minstay
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $289 to $917/night

    Wailea Ekahi 49F

    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. $288 to $395/night

    Shores at Waikoloa 234 at Bo Tree Tower

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $288 to $459/night

    Vista Waikoloa A104

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $288 to $427/night

    Waikoloa Beach Villas E32

    2 BedroomsBathroomsSleeps 5
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $288 to $534/night

    Hali'i Kai at Waikoloa 2B

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $286 to $1,085/night

    Big Island Na Hale O Keauhou F6

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $283 to $415/night

    Pali Ke Kua #103

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $283 to $1,123/night

    Nohonani 102

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $283 to $415/night

    Pali Ke Kua #103

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $282 to $1,486/night

    Wailea Ekolu 502

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $277 to $427/night

    Vista Waikoloa B206

    2 BedroomsBathroomsSleeps 5
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $277 to $416/night

    Waikoloa Beach Villas G2

    2 BedroomsBathroomsSleeps 5
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $274 to $1,110/night

    Wailea Ekolu 208

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $268 to $1,007/night

    Grand Champions 36

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $267 to $1,147/night

    Wailea Ekolu 1405

    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. $266 to $406/night

    Waikoloa Beach Villas M2

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $266 to $395/night

    Fairway Villas Waikoloa A21

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $266 to $373/night

    Fairway Villas Waikoloa O21

    2 BedroomsBathroomsSleeps 5
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $260 to $1,142/night

    Valley Isle 708

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $260 to $1,036/night

    Wailea Ekahi 48E

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $256 to $455/night

    Waikoloa Beach Villas O2

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $256 to $416/night

    Waikoloa Beach Villas P32

    2 BedroomsBathroomsSleeps 5
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $256 to $406/night

    Waikoloa Beach Villas C3

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $252 to $1,007/night

    Big Island Awamoa Hale

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $245 to $629/night

    Pu'ukala Sunset Estate w/ Amazing Ocean Views!

    3 BedroomsBathroomsSleeps 6
    1 night minstay
    FREE CANCELLATION
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $243 to $699/night

    Maalaea Banyans 102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $243 to $784/night

    Grand Champions 68

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $231 to $760/night

    Maui Vista 2416

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $231 to $897/night

    Grand Champions 145

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $231 to $804/night

    Kauai Regency at Poipu Kai #811

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $230 to $635/night

    Big Island Kanaloa at Kona 1301

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