Welcome to Hawaii! Paradise on earth! RedAwning has the perfect vacation rental for your island adventures. Beach bungalows, resort condos, and sun-kissed ocean-front villas await. Browse your island destination using the blue location links below or filter your preferences using the panel to the side. RedAwning offers easy, instant, hotel-style reservations and a simplified booking process so you can have your vacation plans covered in no time.

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  1. $17,975 to $27,561/night

    Kauhale Pilialoha

    10 Bedrooms14 BathroomsSleeps 30
    6 nights minstay
    Pool Hot Tub
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  3. $10,240 to $12,620/night

    Mauna Kea Bluffs #5: La Ikena O Komohana*

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
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  5. $4,194/night

    Kalina at Hapuna Beach

    4 Bedrooms4.5 BathroomsSleeps 10
    5 nights minstay
    Pool Hot Tub
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  7. $3,248 to $5,568/night

    Wailea Inn Maui

    14 Bedrooms13 BathroomsSleeps 32
    2 nights minstay
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  9. $2,673 to $3,119/night

    Blue Mahina at Sunset Beach

    4 BedroomsBathroomsSleeps 11
    7 nights minstay
    FREE CANCELLATION
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  11. $2,505 to $4,766/night

    Mauna Kea Resort Townhouse- Kaunaoa 7B (4BR/4.5BA)

    4 Bedrooms4.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
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  13. $2,495 to $4,990/night

    Hanalei Beachfront

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
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  15. $2,495 to $2,673/night

    Helen's Beach House

    6 BedroomsBathroomsSleeps 14
    7 nights minstay
    Pool
    FREE CANCELLATION
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  17. $2,495 to $2,673/night

    Kailua Beachside

    4 BedroomsBathroomsSleeps 14
    7 nights minstay
    Pool
    FREE CANCELLATION
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  19. $2,203 to $3,457/night

    4BD Villas at Mauna Kea #21

    4 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
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  21. $1,995 to $3,392/night

    Luxury 6 bedroom Penthouse w/ Pool & Hot Tub- Steps ...

    6 BedroomsBathroomsSleeps 16
    2 nights minstay
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  23. $1,986 to $3,779/night

    Hale Pua

    5 BedroomsBathroomsSleeps 16
    2 nights minstay
    Pool Hot Tub
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  25. $1,900 to $2,138/night

    Makena Aloha Estate

    4 BedroomsBathroomsSleeps 10
    5 nights minstay
    Pool Hot Tub
  26. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  27. $1,871 to $3,743/night

    Hale Maluhia Hanalei

    1 Bedroom1.5  BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
  28. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  29. $1,871 to $2,339/night

    Pinetrees Beach Villa

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
  30. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  31. $1,871 to $3,119/night

    Hale I'a U'i- Beautiful Fish House

    4 Bedrooms5.5 BathroomsSleeps 10
    3 nights minstay
    Hot Tub
    FREE CANCELLATION
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  33. $1,797 to $2,217/night

    Hale Waiulu

    3 Bedrooms3.5 BathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
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  35. $1,672 to $2,981/night

    Champion Ridge Home

    4 Bedrooms4.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
  36. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  37. $1,646 to $4,967/night

    3BD Golf Villa (3101 Kumukehu) at Four Seasons Resort Hu...

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $1,613 to $3,219/night

    Hillside Villa 7101

    3 Bedrooms BathroomSleeps 6
    2 nights minstay
    Pool
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  41. $1,605 to $4,585/night

    5BD Estate Home Fairways South #18 at Mauna Kea Resort

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
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  43. $1,553 to $3,398/night

    Laulea Kailani Villa (KAUAI)

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $1,553 to $4,900/night

    Haena Beach House TVNC#1258

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
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  47. $1,497 to $2,495/night

    Huaka Mahina

    4 Bedrooms4.5 BathroomsSleeps 8
    5 nights minstay
    Pool
    FREE CANCELLATION
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $1,434 to $4,527/night

    Mermaid Cove

    4 BedroomsBathroomsSleeps 13
    2 nights minstay
    Pool Hot Tub
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  51. $1,434 to $3,100/night

    Ka'ulu Villa 129B

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $1,413 to $1,906/night

    Moloa'a Bay Villa and Cottage

    5 BedroomsBathroomsSleeps 12
    3 nights minstay
  54. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  55. $1,404 to $4,289/night

    Lau'lea at the Mauna Lani*

    4 Bedrooms4.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $1,395/night

    Kona Bubbles

    4 Bedrooms4.5 BathroomsSleeps 8
    7 nights minstay
    Pool
    FREE CANCELLATION
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $1,373 to $3,457/night

    House of the Turtle at Champion Ridge, Mauna Lani (CR 18...

    4 Bedrooms4.5 BathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $1,318 to $2,876/night

    Hale Keanu

    4 Bedrooms4.5 BathroomsSleeps 9
    5 nights minstay
    Pool Hot Tub
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $1,315 to $3,226/night

    O'oma Plantation

    5 BedroomsBathroomsSleeps 16
    2 nights minstay
    Pool Hot Tub
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $1,303 to $1,404/night

    Makalae

    5 BedroomsBathroomsSleeps 10
    3 nights minstay
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $1,250 to $3,226/night

    Ali'i Point

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $1,248 to $1,516/night

    Hale Maluhia Waialua

    3 Bedrooms3.5 BathroomsSleeps 8
    7 nights minstay
    FREE CANCELLATION
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $1,241/night

    Hana Estate

    5 BedroomsBathroomsSleeps 10
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $1,220 to $3,600/night

    3BD Villas at Mauna Kea #39

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $1,196 to $2,743/night

    Wai'ulu Villa 115D

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $1,195 to $3,799/night

    Turtle Bay Villas 216

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $1,188 to $4,533/night

    Diamond Head Tiki Estate

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $1,182 to $3,312/night

    3BD Ke Kailani (1C) at Mauna Lani

    3 Bedrooms3.5 BathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $1,168/night

    Villa Cinco Resort at Kona Plantation Estates

    5 BedroomsBathroomsSleeps 15
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $1,166 to $2,743/night

    Fairway Villa 104A

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $1,166 to $2,743/night

    Fairways Villa 120A

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $1,160 to $3,411/night

    4BD Estate Home at Puako Bay (74)

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $1,152/night

    Pu'uwai Hale

    4 BedroomsBathroomsSleeps 8
    3 nights minstay
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $1,137 to $2,656/night

    Ke Kailani Hale A2

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $1,137 to $2,743/night

    Ali'i Villa

    4 Bedrooms4.5 BathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $1,123 to $1,871/night

    Hale Hoku

    5 BedroomsBathroomsSleeps 12
    3 nights minstay
    FREE CANCELLATION
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $1,117 to $1,685/night

    Aloha Spirit Maui

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $1,094 to $1,413/night

    Moloa'a Bay Villa

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $1,077 to $3,143/night

    3BD Estate Home at Puako Bay (10D)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $1,076 to $1,909/night

    Wai'ula'ula #344

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $1,060 to $2,246/night

    King Hale

    4 BedroomsBathroomsSleeps 10
    3 nights minstay
    FREE CANCELLATION
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $1,059 to $1,553/night

    Villages at Mauna Lani Resort Unit # 728

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $1,056 to $3,076/night

    3BD Hali'ipua Villa (108) at Four Seasons Resort Hu...

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $1,018 to $1,880/night

    Mauna Kea Villas #13

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $1,018 to $1,910/night

    Wai'ula'ula 318

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $1,013 to $2,949/night

    3BD Fairways Villa (116D) at Four Seasons Resort Hualala...

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $998 to $1,996/night

    Kai Halulu

    3 Bedrooms3.5 BathroomsSleeps 7
    3 nights minstay
    Hot Tub
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $973 to $2,018/night

    Elua Lani 803

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pool Hot Tub
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $923 to $1,434/night

    Hale Kauka

    3 Bedrooms2.5 BathroomsSleeps 7
    2 nights minstay
    Pool
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $899 to $1,553/night

    Mauna Lani Terrace A303

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $899 to $2,290/night

    Mana Alana at Poipu

    3 Bedrooms3.5 BathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $895 to $2,367/night

    3BD Wai'ula'ula Villa (345) at Mauna Kea Resor...

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $839 to $1,553/night

    Pohaku Villa

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $813 to $1,438/night

    Kapalua Bay Villa 22G2 Gold Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $811 to $1,871/night

    Hanalei Bluff

    3 Bedrooms3.5 BathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $806 to $971/night

    Mahana 519

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $781 to $1,438/night

    Kapalua Bay Villa 30B3 Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $781 to $1,406/night

    Kapalua Bay Villa 35B3 Gold Ocean Front

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $780 to $1,711/night

    Hale Emmalani

    4 Bedrooms3.5 BathroomsSleeps 11
    2 nights minstay
    Hot Tub
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $780 to $1,256/night

    Hale Poola

    5 BedroomsBathroomsSleeps 12
    2 nights minstay
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $780 to $1,811/night

    Hokulani Villa

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $766/night

    Hale Honu-Oceanfront

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    Hot Tub
    FREE CANCELLATION
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $763 to $2,412/night

    2BD Hainoa Villa (2901B) at Four Seasons Resort Hualalai...

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $760 to $1,941/night

    Mauna Lani KaMilo Home (349)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $759/night

    Mauna Lani Terrace D201

    2 Bedrooms2.5 BathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $749 to $1,871/night

    Hanalei Bay View

    4 BedroomsBathroomsSleeps 12
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $748 to $1,060/night

    Malapua

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $744 to $2,299/night

    Blue Hawaii

    3 Bedrooms3.5 BathroomsSleeps 14
    2 nights minstay
    Pool
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $742 to $798/night

    Hale Mana

    4 BedroomsBathroomsSleeps 8
    7 nights minstay
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $740 to $2,016/night

    Hale Lalea Ko Olina Beach Villa (B310)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $731 to $1,900/night

    Hale Kai O'Kona #7

    4 BedroomsBathroomsSleeps 8
    2 nights minstay
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $720 to $1,732/night

    Plantation Cottage at Poipu

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $720 to $1,226/night

    Mango Sunsets

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $719 to $1,909/night

    Nai'a Hale

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $719 to $1,137/night

    Island Time- Holua Kai

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $717 to $1,865/night

    Punahele

    3 Bedrooms2.5 BathroomsSleeps 8
    3 nights minstay
    Hot Tub
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $714 to $1,601/night

    Ohana Kamalani

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $708 to $1,916/night

    Hoku'Ea Hale

    3 Bedrooms2.5 BathroomsSleeps 10
    2 nights minstay
    Hot Tub
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $696 to $829/night

    Whaler 859

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $695 to $1,678/night

    Keauhou Elima

    4 Bedrooms5.5 BathroomsSleeps 10
    5 nights minstay
    Pool
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $686 to $936/night

    Hale Nanea

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $686 to $1,060/night

    Camp Magic 1

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $686 to $936/night

    Hale Lani

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $674 to $811/night

    Kaanapali Shores 515

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $668/night

    Ali'i Point #5 Oceanfront

    3 Bedrooms3.5 BathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $661 to $1,277/night

    Hale Anu Keanu

    4 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Hot Tub
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $661 to $1,018/night

    Kona Blue Vacations Holua Kai

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