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  1. $3,278 to $8,050/night

    Beach Castle

    7 BedroomsBathroomsSleeps 18
    3 nights minstay
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  3. $3,035 to $11,599/night

    Wailea Beach Villa B102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  5. $2,958 to $11,468/night

    Wailea Beach Villa B202

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  7. $2,532 to $10,440/night

    Andaz Villa 810

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  9. $1,950 to $2,249/night

    Puuwai Alii Estate

    5 Bedrooms5.5 BathroomsSleeps 8
    7 nights minstay
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  11. $1,846 to $6,200/night

    Halama Hale Private Home

    4 Bedrooms3.5 BathroomsSleeps 14
    2 nights minstay
    Pool
    FREE CANCELLATION
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  13. $1,616 to $5,653/night

    Stunning penthouse with 3,600 sq. ft. of luxury!

    3 BedroomsBathroomsSleeps 12
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
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  15. $1,613 to $62,008/night

    8BR- Quartz Mountain Manor

    8 BedroomsBathroomsSleeps 20
    2 nights minstay
    Pool Hot Tub Pets OK
    FREE CANCELLATION
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  17. $1,457 to $20,997/night

    7BR- Wild West Estate

    7 BedroomsBathroomsSleeps 18
    2 nights minstay
    Pool Hot Tub Pets OK
    FREE CANCELLATION
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  19. $1,443 to $5,169/night

    The Cove Hale

    4 BedroomsBathroomsSleeps 16
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  21. $1,320 to $4,721/night

    3 Bedroom Penthouse at the base of Canyons

    3 Bedrooms3.5 BathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
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  23. $1,248 to $1,605/night

    Swami's Sunset

    3 BedroomsBathroomsSleeps 7
    30 nights minstay
    Pool Hot Tub
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  25. $1,220 to $4,156/night

    Big Island Hale Kaheka 6592

    1 Bedroom2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  27. $1,202 to $1,459/night

    Luxury Makalae Home close to Water Activities

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
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  29. $1,202 to $1,459/night

    Makalae

    5 BedroomsBathroomsSleeps 10
    3 nights minstay
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  31. $1,173/night

    Ritz Carlton Coconut Grove Waterview 2 BR Apt

    2 Bedrooms2.5 BathroomsSleeps 4
    30 nights minstay
    Pool
    FREE CANCELLATION
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  33. $1,152 to $5,344/night

    Ho'olei 17-1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  35. $1,138 to $36,270/night

    10BR- Valley Vista Mansion

    10 BedroomsBathroomsSleeps 26
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  37. $1,126 to $4,236/night

    Big Island Hualalai 133C

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  39. $1,097 to $8,557/night

    7BR- Dream Maker Villa

    7 BedroomsBathroomsSleeps 16
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  41. $1,096 to $5,113/night

    Wailea Beach Villa I503

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  43. $1,093 to $22,427/night

    9BR- The Cochise Estate

    9 BedroomsBathroomsSleeps 22
    2 nights minstay
    Pool Hot Tub Pets OK
    FREE CANCELLATION
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  45. $1,070 to $2,850/night

    Casa Cielo

    6 Bedrooms5.5 BathroomsSleeps 12
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  47. $1,061 to $7,914/night

    7BR- Orangewood Mansion

    7 BedroomsBathroomsSleeps 16
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  49. $1,054 to $8,427/night

    6BR- Paradise Palace Estate

    6 BedroomsBathroomsSleeps 18
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  51. $1,038 to $4,344/night

    Ho'olei 112-5

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  53. $1,038 to $3,879/night

    Wailea Beach Villa H202

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  55. $1,030 to $3,783/night

    Gemini's Mountain Retreat! Private Hot Tub! Free Sh...

    4 BedroomsBathroomsSleeps 17
    2 nights minstay
    Hot Tub
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $1,017 to $2,248/night

    Baydream

    4 Bedrooms3.5 BathroomsSleeps 23
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  59. $1,017 to $3,146/night

    Anahola Aloha Beach House

    4 BedroomsBathroomsSleeps 12
    3 nights minstay
    Hot Tub
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  61. $1,010 to $4,779/night

    Aspen Alps Apartment #809

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  63. $998 to $1,586/night

    Kahana Outrigger #1A2

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
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  65. $989 to $2,906/night

    Honua Kai Konea 250

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  67. $989 to $7,103/night

    The Timber Lodge 957

    7 BedroomsBathroomsSleeps 19
    2 nights minstay
    Hot Tub
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  69. $987 to $4,528/night

    Ho'olei 39-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  71. $981 to $4,337/night

    Ho'olei 21-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  73. $961 to $1,108/night

    Pu'uwai Hale

    4 Bedrooms4.5 BathroomsSleeps 8
    3 nights minstay
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  75. $960 to $4,785/night

    Aspen Alps Apartment #804

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  77. $936 to $1,411/night

    Sands Of Kahana 384

    1 BedroomBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $923 to $4,451/night

    Ho'olei 24-4

    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. $923 to $3,670/night

    Ho'olei 55-3

    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. $923 to $2,740/night

    Polo Beach Club 106

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  85. $923 to $4,087/night

    Ho'olei 24-1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  87. $923 to $2,546/night

    Big Island Holua Kai 7061

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $922 to $3,198/night

    Maui Dolphin House

    4 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
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  91. $921 to $4,211/night

    Ho'olei 55-2

    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. $918 to $2,066/night

    New Snowmass View Townhome Ski-in/ Ski-Out

    2 Bedrooms2.5 BathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $908 to $18,594/night

    6BR- Mountainside Manor

    6 BedroomsBathroomsSleeps 16
    2 nights minstay
    Pool
    FREE CANCELLATION
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $880 to $2,359/night

    Mad Hatter @ Storey Lake by Shine Villas #827

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $866 to $3,860/night

    Ho'olei 24-6

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $866 to $1,559/night

    Kahana Outrigger #2B1

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $865 to $3,810/night

    Ho'olei 12-4

    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. $839 to $6,211/night

    Private 4Br Residence In Vail Village with Full Kitchen,...

    4 BedroomsBathroomsSleeps 10
    1 night minstay
    Hot Tub
    FREE CANCELLATION
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $837 to $1,583/night

    Kapalua Ridge Villas-#323

    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. $834 to $21,587/night

    8BR- Casa Palacio Mansion

    8 BedroomsBathroomsSleeps 20
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $808 to $3,038/night

    Aspen Alps Apartment #806

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $808 to $2,974/night

    Wailea Beach Villa J106

    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. $803 to $2,413/night

    Taylor Ct. 525, Marco Island Vacation Rental

    4 BedroomsBathroomsSleeps 8
    7 nights minstay
    Pool Hot Tub
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $803 to $3,345/night

    Sand Cove Villa

    7 BedroomsBathroomsSleeps 25
    2 nights minstay
    Pool Hot Tub
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $788 to $5,639/night

    920 E La Tania

    4 BedroomsBathroomsSleeps 8
    2 nights minstay
    Hot Tub
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $767 to $2,974/night

    Wailea Beach Villa H102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $763 to $6,099/night

    80 Old Town Masterpiece

    6 Bedrooms6.5 BathroomsSleeps 12
    2 nights minstay
    Hot Tub
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $759 to $20,000/night

    Luxury 4 Bedroom Steps from Skiing and Winter Activities...

    4 BedroomsBathroomsSleeps 10
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $759 to $20,000/night

    Penthouse 4 Bedroom Condo at Base of Peak 8

    4 BedroomsBathroomsSleeps 10
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $759 to $10,321/night

    Sorrento Vacation Rental

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub Pets OK
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $751 to $808/night

    Molokama Vacation Home in Hanalei Bay Near Beach

    4 BedroomsBathroomsSleeps 8
    3 nights minstay
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $750 to $3,970/night

    Wailea Beach Villa I204

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $745 to $1,715/night

    Blessed at the Beach- Gulf Side- Private (heated) pool- ...

    5 BedroomsBathroomsSleeps 12
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $736 to $8,601/night

    Sardinia Vacation Rental

    4 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $735 to $1,575/night

    Holua House#28

    3 Bedrooms3.5 BathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $735 to $1,427/night

    Hale Lani

    1 Bedroom BathroomSleeps 2
    2 nights minstay
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $727 to $6,548/night

    Norfolk Mountain Fantasy! 1121

    5 Bedrooms5.5 BathroomsSleeps 11
    2 nights minstay
    Hot Tub
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $723 to $11,652/night

    6BR- Old Town Scottsdale Penthouse

    6 BedroomsBathroomsSleeps 20
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $721 to $2,362/night

    Noelani 306

    Multiple Units Available
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $716 to $2,130/night

    Wailea Elua 2109

    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. $715 to $2,961/night

    Exclusive Pool Villa

    5 BedroomsBathroomsSleeps 20
    2 nights minstay
    Pool Hot Tub
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $715 to $3,850/night

    Desert Mirage

    5 BedroomsBathroomsSleeps 22
    2 nights minstay
    Pool Hot Tub
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $701 to $3,465/night

    Wailea Elua 2305

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $687 to $1,176/night

    Mana Kai #412

    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. $683 to $1,037/night

    Kaanapali Shores #160

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $678 to $2,906/night

    Newly updated in Canyons Village next to slopes

    2 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $678 to $2,906/night

    Exquisite Condo, Great for Families, Ski in/out

    2 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $668 to $2,676/night

    Makena Surf B305

    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. $660 to $4,892/night

    Living On The Ledge

    4 Bedrooms4.5 BathroomsSleeps 18
    2 nights minstay
    Pool Hot Tub
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $659 to $2,025/night

    Noelani 307

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $656 to $2,986/night

    Polo Beach Club 107

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $647 to $1,244/night

    Kahana Outrigger #4B2

    3 BedroomsBathroomsSleeps 9
    2 nights minstay
    FREE CANCELLATION
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $645 to $2,485/night

    Breeze Away- 2525 Bienville Blvd

    5 BedroomsBathroomsSleeps 20
    3 nights minstay
    Pool Pets OK
    FREE CANCELLATION
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $645 to $2,360/night

    Lemon Breeze- 2521 Bienville

    5 BedroomsBathroomsSleeps 25
    3 nights minstay
    Pool Pets OK
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $638 to $1,573/night

    Whispering Breezes at Windy Hill

    4 BedroomsBathroomsSleeps 12
    2 nights minstay
    Pool Pets OK
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $635 to $756/night

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $635 to $756/night

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $635 to $756/night

    Waipouli Beach Resort G-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $635 to $756/night

    Waipouli Beach Resort G-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $632 to $1,295/night

    Seven Springs 4 BR Deluxe Townhouse, Sleeps 11!

    3 BedroomsBathroomsSleeps 11
    1 night minstay
    Pool Pets OK
    FREE CANCELLATION
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $630 to $8,161/night

    2 Lucky Star at Belle Arbor

    4 Bedrooms4.5 BathroomsSleeps 12
    2 nights minstay
    Hot Tub
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $629 to $968/night

    Kaanapali Shores #255

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $625 to $935/night

    The Mahana #1205

    1 BedroomBathroomsSleeps 2
    2 nights minstay
    FREE CANCELLATION
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $625 to $788/night

    The Mahana #1217

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $621 to $1,116/night

    Kahana Sunset A7

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool
  200. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations