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. $2,900 to $3,088/night

    Hale Nui

    5 Bedrooms5.5 BathroomsSleeps 10
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  11. $2,852 to $3,743/night

    Dolphin House

    6 BedroomsBathroomsSleeps 10
    7 nights minstay
    FREE CANCELLATION
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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

    Kailua Beachside

    4 BedroomsBathroomsSleeps 14
    7 nights minstay
    Pool
    FREE CANCELLATION
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  17. $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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  19. $2,115 to $3,743/night

    Napili Ocean Front House 43

    5 BedroomsBathroomsSleeps 10
    5 nights minstay
    Hot Tub
    FREE CANCELLATION
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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. $1,989 to $4,035/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
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  27. $1,871 to $2,339/night

    Pinetrees Beach Villa

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
  28. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  29. $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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  31. $1,797 to $2,217/night

    Hale Waiulu

    3 Bedrooms3.5 BathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
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  33. $1,695 to $3,743/night

    Hale Maluhia Hanalei

    1 Bedroom1.5  BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
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  35. $1,692 to $2,494/night

    Rainbow Hale Estate

    4 Bedrooms3.5 BathroomsSleeps 8
    5 nights minstay
    Pool
  36. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  37. $1,672 to $2,981/night

    Champion Ridge Home

    4 Bedrooms4.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $1,646 to $5,763/night

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

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  40. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  41. $1,613 to $3,219/night

    Hillside Villa 7101

    3 Bedrooms BathroomSleeps 6
    2 nights minstay
    Pool
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  43. $1,605 to $5,315/night

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

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
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  45. $1,553 to $3,398/night

    Laulea Kailani Villa (KAUAI)

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool
  46. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  47. $1,553 to $4,902/night

    Haena Beach House TVNC#1258

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
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  49. $1,497 to $2,495/night

    Huaka Mahina

    4 Bedrooms4.5 BathroomsSleeps 8
    5 nights minstay
    Pool
    FREE CANCELLATION
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  51. $1,497 to $2,139/night

    Laau Paina

    5 BedroomsBathroomsSleeps 10
    7 nights minstay
    FREE CANCELLATION
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $1,434 to $5,252/night

    Mermaid Cove

    4 BedroomsBathroomsSleeps 13
    2 nights minstay
    Pool Hot Tub
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  55. $1,434 to $3,100/night

    Ka'ulu Villa 129B

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $1,413 to $1,906/night

    Moloa'a Bay Villa and Cottage

    5 BedroomsBathroomsSleeps 12
    3 nights minstay
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $1,395/night

    Kona Bubbles

    4 Bedrooms4.5 BathroomsSleeps 8
    7 nights minstay
    Pool
    FREE CANCELLATION
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $1,373 to $4,001/night

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

    4 Bedrooms4.5 BathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $1,372 to $2,246/night

    King Hale

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
    FREE CANCELLATION
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $1,318 to $2,876/night

    Hale Keanu

    4 Bedrooms4.5 BathroomsSleeps 9
    5 nights minstay
    Pool Hot Tub
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $1,315 to $3,737/night

    O'oma Plantation

    5 BedroomsBathroomsSleeps 16
    2 nights minstay
    Pool Hot Tub
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $1,303 to $1,404/night

    Makalae

    5 BedroomsBathroomsSleeps 10
    3 nights minstay
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $1,250 to $3,737/night

    Ali'i Point

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $1,248 to $1,516/night

    Hale Maluhia Waialua

    3 Bedrooms3.5 BathroomsSleeps 8
    7 nights minstay
    FREE CANCELLATION
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $1,220 to $4,166/night

    3BD Villas at Mauna Kea #39

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $1,196 to $2,743/night

    Wai'ulu Villa 115D

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $1,195 to $3,772/night

    Turtle Bay Villas 216

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $1,188 to $4,488/night

    Diamond Head Tiki Estate

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $1,182 to $3,832/night

    3BD Ke Kailani (1C) at Mauna Lani

    3 Bedrooms3.5 BathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $1,168/night

    Villa Cinco Resort at Kona Plantation Estates

    5 BedroomsBathroomsSleeps 15
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $1,166 to $2,743/night

    Fairway Villa 104A

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $1,166 to $2,743/night

    Fairways Villa 120A

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $1,160 to $4,103/night

    4BD Estate Home at Puako Bay (74)

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $1,137 to $2,743/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 $1,990/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. $1,077 to $3,636/night

    3BD Estate Home at Puako Bay (10D)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $1,076 to $1,909/night

    Wai'ula'ula #344

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $1,059 to $1,553/night

    Villages at Mauna Lani Resort Unit # 728

    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. $1,056 to $3,557/night

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

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $1,047 to $1,999/night

    Mauna Kea Villas #13

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $1,018 to $1,910/night

    Wai'ula'ula 318

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $1,013 to $3,414/night

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

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $903 to $1,434/night

    Hale Kauka

    3 Bedrooms2.5 BathroomsSleeps 7
    2 nights minstay
    Pool
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $903 to $2,018/night

    Elua Lani 803

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pool Hot Tub
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $899 to $1,553/night

    Mauna Lani Terrace A303

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $875 to $2,732/night

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

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $839 to $1,553/night

    Pohaku Villa

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $813 to $1,438/night

    Kapalua Bay Villa 22G2 Gold Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $811 to $1,871/night

    Hanalei Bluff

    3 Bedrooms3.5 BathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $790 to $1,051/night

    Hale Ola Kai

    3 Bedrooms2.5 BathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $781 to $1,438/night

    Kapalua Bay Villa 30B3 Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $781 to $1,406/night

    Kapalua Bay Villa 35B3 Gold Ocean Front

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $780 to $1,256/night

    Hale Poola

    5 BedroomsBathroomsSleeps 12
    2 nights minstay
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $780 to $1,811/night

    Hokulani Villa

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $775 to $1,668/night

    Hale Akala Falls Ko Olina Beach Villa (O121)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $766 to $846/night

    Hale Honu-Oceanfront

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    Hot Tub
    FREE CANCELLATION
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $765 to $2,505/night

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

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $760 to $2,238/night

    Mauna Lani KaMilo Home (349)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $759/night

    Mauna Lani Terrace D201

    2 Bedrooms2.5 BathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $748 to $1,060/night

    Malapua

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $744 to $2,659/night

    Blue Hawaii

    3 Bedrooms3.5 BathroomsSleeps 14
    2 nights minstay
    Pool
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $742 to $798/night

    Hale Mana

    4 BedroomsBathroomsSleeps 8
    7 nights minstay
    FREE CANCELLATION
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $740 to $2,016/night

    Hale Lalea Ko Olina Beach Villa (B310)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $720 to $1,226/night

    Mango Sunsets

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $719 to $2,221/night

    Nai'a Hale

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $719 to $1,137/night

    Island Time- Holua Kai

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $717 to $904/night

    Hale Koaniani

    3 Bedrooms2.5 BathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $717 to $1,865/night

    Punahele

    3 Bedrooms2.5 BathroomsSleeps 8
    3 nights minstay
    Hot Tub
    FREE CANCELLATION
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $708 to $2,209/night

    Hoku'Ea Hale

    3 Bedrooms2.5 BathroomsSleeps 10
    2 nights minstay
    Hot Tub
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $695 to $1,678/night

    Keauhou Elima

    4 Bedrooms5.5 BathroomsSleeps 10
    5 nights minstay
    Pool
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $688 to $1,152/night

    Pu'uwai Hale

    4 BedroomsBathroomsSleeps 8
    3 nights minstay
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $686 to $873/night

    Lokelani Hale

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $686 to $936/night

    Hale A Kai

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    FREE CANCELLATION
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $686 to $936/night

    Hale Nanea

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $686 to $1,060/night

    Camp Magic 1

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $686 to $936/night

    Hale Lani

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $686 to $936/night

    Queens Bath Lookout

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool
    FREE CANCELLATION
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $668 to $846/night

    Ali'i Point #5 Oceanfront

    3 Bedrooms3.5 BathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $664/night

    White Sands Village#213

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $661 to $2,193/night

    Hale Kai O'Kona #7

    4 BedroomsBathroomsSleeps 8
    2 nights minstay
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $661 to $1,278/night

    Hale Anu Keanu

    4 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Hot Tub
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $661 to $1,515/night

    Hale Emmalani

    4 Bedrooms3.5 BathroomsSleeps 11
    2 nights minstay
    Hot Tub
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $656 to $906/night

    Kapalua Bay Villa 21G4 Gold Beach Front

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $656 to $938/night

    Kapalua Bay Villa 21G5 Gold Beach Front

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $641 to $992/night

    Turtle Rock

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