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. $7,860 to $12,620/night

    Kailua Shores Estate 8 Bedroom

    8 BedroomsBathroomsSleeps 18
    2 nights minstay
    Pool
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  7. $4,194/night

    Kalina at Hapuna Beach

    4 Bedrooms4.5 BathroomsSleeps 10
    5 nights minstay
    Pool Hot Tub
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  9. $3,780 to $7,560/night

    Lani Kai

    4 BedroomsBathroomsSleeps 8
    3 nights minstay
    Hot Tub
    FREE CANCELLATION
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  11. $3,695 to $6,075/night

    Mauna Kea Resort Bluffs 22- The Beach House

    4 Bedrooms5.5 BathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
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  13. $3,695 to $7,265/night

    Mauna Kea Resort Bluffs 22- The Beach House

    4 Bedrooms5.5 BathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
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  15. $3,248 to $5,568/night

    Wailea Inn Maui

    14 Bedrooms13 BathroomsSleeps 32
    2 nights minstay
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  17. $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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  19. $2,880 to $3,780/night

    Dolphin House

    6 BedroomsBathroomsSleeps 10
    7 nights minstay
    FREE CANCELLATION
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  21. $2,520 to $5,040/night

    Hanalei Beachfront

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
  22. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  23. $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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  25. $2,078 to $3,780/night

    Napili Ocean Front House 43

    5 BedroomsBathroomsSleeps 10
    5 nights minstay
    Hot Tub
    FREE CANCELLATION
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  27. $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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  29. $1,900 to $2,138/night

    Makena Aloha Estate

    4 BedroomsBathroomsSleeps 10
    5 nights minstay
    Pool Hot Tub
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  31. $1,890 to $3,780/night

    Hale Maluhia Hanalei

    1 Bedroom1.5  BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
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  33. $1,890/night

    Weke Road Beachfront Cottage

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
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  35. $1,890 to $2,363/night

    Pinetrees Beach Villa

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
  36. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  37. $1,890 to $3,150/night

    Hale I'a U'i- Beautiful Fish House

    4 Bedrooms5.5 BathroomsSleeps 10
    3 nights minstay
    Hot Tub
    FREE CANCELLATION
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $1,890 to $2,520/night

    Kailua Beachside

    4 BedroomsBathroomsSleeps 14
    7 nights minstay
    Pool
    FREE CANCELLATION
  40. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  41. $1,870 to $2,494/night

    Wilikoki House

    6 BedroomsBathroomsSleeps 10
    5 nights minstay
    FREE CANCELLATION
  42. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  43. $1,733 to $3,812/night

    Ikena Lani

    5 BedroomsBathroomsSleeps 12
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $1,692 to $2,494/night

    Rainbow Hale Estate

    4 Bedrooms3.5 BathroomsSleeps 8
    5 nights minstay
    Pool
  46. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  47. $1,672 to $2,981/night

    Champion Ridge Home

    4 Bedrooms4.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $1,646 to $4,964/night

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

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
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  51. $1,613 to $3,219/night

    Hillside Villa 7101

    3 Bedrooms BathroomSleeps 6
    2 nights minstay
    Pool
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  53. $1,605 to $5,192/night

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

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
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  55. $1,526/night

    Hale Lani

    4 BedroomsBathroomsSleeps 14
    3 nights minstay
    Pool
    FREE CANCELLATION
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $1,512 to $2,520/night

    Huaka Mahina

    4 Bedrooms4.5 BathroomsSleeps 8
    5 nights minstay
    Pool
    FREE CANCELLATION
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $1,512 to $2,161/night

    Laau Paina

    5 BedroomsBathroomsSleeps 10
    7 nights minstay
    FREE CANCELLATION
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $1,434 to $4,524/night

    Mermaid Cove

    4 BedroomsBathroomsSleeps 13
    2 nights minstay
    Pool Hot Tub
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  63. $1,434 to $3,100/night

    Ka'ulu Villa 129B

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $1,413 to $1,732/night

    Moloa'a Bay Villa and Cottage

    5 BedroomsBathroomsSleeps 12
    3 nights minstay
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $1,395/night

    Kona Bubbles

    4 Bedrooms4.5 BathroomsSleeps 8
    7 nights minstay
    Pool
    FREE CANCELLATION
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $1,330 to $3,857/night

    Hale Pua

    5 BedroomsBathroomsSleeps 16
    2 nights minstay
    Pool Hot Tub
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $1,318 to $2,268/night

    King Hale

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
    FREE CANCELLATION
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $1,318 to $2,876/night

    Hale Keanu

    4 Bedrooms4.5 BathroomsSleeps 9
    5 nights minstay
    Pool Hot Tub
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $1,315 to $3,224/night

    O'oma Plantation

    5 BedroomsBathroomsSleeps 16
    2 nights minstay
    Pool Hot Tub
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $1,314 to $3,565/night

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

    4 Bedrooms4.5 BathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $1,291 to $4,458/night

    Haena Beach House TVNC#1258

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $1,285 to $4,009/night

    4BD Estate Home at Puako Bay (74)

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $1,260 to $1,531/night

    Hale Maluhia Waialua

    3 Bedrooms3.5 BathroomsSleeps 8
    7 nights minstay
    FREE CANCELLATION
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $1,250 to $3,224/night

    Ali'i Point

    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. $1,220 to $4,070/night

    3BD Villas at Mauna Kea #39

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $1,208 to $3,398/night

    Laulea Kailani Villa (KAUAI)

    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. $1,206 to $1,404/night

    Makalae

    5 BedroomsBathroomsSleeps 10
    3 nights minstay
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $1,196 to $2,743/night

    Wai'ulu Villa 115D

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $1,188 to $3,565/night

    Diamond Head Tiki Estate

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $1,177 to $3,565/night

    3BD Ke Kailani (1C) at Mauna Lani

    3 Bedrooms3.5 BathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $1,168/night

    Villa Cinco Resort at Kona Plantation Estates

    5 BedroomsBathroomsSleeps 15
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $1,166 to $2,743/night

    Fairway Villa 104A

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $1,166 to $2,743/night

    Fairways Villa 120A

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $1,134 to $1,890/night

    Hale Hoku

    5 BedroomsBathroomsSleeps 12
    3 nights minstay
    FREE CANCELLATION
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $1,128 to $2,010/night

    Aloha Spirit Maui

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $1,077 to $3,553/night

    3BD Estate Home at Puako Bay (10D)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $1,076 to $2,961/night

    Turtle Bay Villas 216

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $1,076 to $1,909/night

    Wai'ula'ula #344

    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. $1,059 to $1,553/night

    Villages at Mauna Lani Resort Unit # 728

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $1,056 to $3,477/night

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

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $1,047 to $1,999/night

    Mauna Kea Villas #13

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $1,018 to $1,910/night

    Wai'ula'ula 318

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $1,013 to $2,946/night

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

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $968 to $1,688/night

    Diamond Head Beach Hotel Rooftop 1402

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $945 to $1,890/night

    Hanalei Bluff

    3 Bedrooms3.5 BathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $882 to $1,008/night

    Kumulani

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $868 to $1,120/night

    Hanalei Beach House: Steps to Surfing and Pier

    2 BedroomsBathroomsSleeps 4
    1 night minstay
    FREE CANCELLATION
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $854 to $1,955/night

    Hale Pulelehua with Guest House TVNC#1238

    5 Bedrooms3.5 BathroomsSleeps 10
    2 nights minstay
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $833 to $2,743/night

    Ali'i Villa

    4 Bedrooms4.5 BathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $833 to $2,478/night

    Ke Kailani Hale A2

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $833 to $2,296/night

    Hale Lalea Ko Olina Beach Villa (B310)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $825 to $1,908/night

    Nai'a Hale

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $819 to $1,134/night

    Kekua

    4 BedroomsBathroomsSleeps 9
    3 nights minstay
    Pool
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $819 to $1,890/night

    Mauna Pua- A 7 bedroom Kauai Vacation Rental

    7 BedroomsBathroomsSleeps 14
    3 nights minstay
    FREE CANCELLATION
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $815 to $1,858/night

    Hale Pulelehua TVNC#1238

    4 Bedrooms2.5 BathroomsSleeps 8
    2 nights minstay
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $813 to $1,438/night

    Kapalua Bay Villa 21G2 Gold Beach Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $813 to $1,438/night

    Kapalua Bay Villa 22G2 Gold Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $801 to $2,673/night

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

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $790 to $1,051/night

    Hale Ola Kai

    3 Bedrooms2.5 BathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $781 to $906/night

    Kapalua Bay Villa 35B3 Gold Ocean Front

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $780 to $1,256/night

    Hale Poola

    5 BedroomsBathroomsSleeps 12
    2 nights minstay
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $766 to $846/night

    Hale Honu-Oceanfront

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    Hot Tub
    FREE CANCELLATION
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $760 to $1,699/night

    Elua Lani 803

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pool Hot Tub
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $759/night

    Mauna Lani Terrace D201

    2 Bedrooms2.5 BathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $750 to $806/night

    Hale Mana

    4 BedroomsBathroomsSleeps 8
    7 nights minstay
    FREE CANCELLATION
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $750 to $1,406/night

    Kapalua Bay Villa 32B2 Gold Ocean View

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $750 to $2,505/night

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

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $748 to $1,060/night

    Malapua

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $745 to $2,139/night

    Hale Pumehana Ko Olina Beach Villa (O1202)

    3 Bedrooms2.5 BathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $745 to $2,139/night

    Hale Akala Falls Ko Olina Beach Villa (O121)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $744 to $2,261/night

    Blue Hawaii

    3 Bedrooms3.5 BathroomsSleeps 14
    2 nights minstay
    Pool
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $725 to $1,884/night

    Punahele

    3 Bedrooms2.5 BathroomsSleeps 8
    3 nights minstay
    Hot Tub
    FREE CANCELLATION
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $720 to $1,226/night

    Mango Sunsets

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $717 to $904/night

    Hale Koaniani

    3 Bedrooms2.5 BathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $708 to $1,553/night

    Mauna Lani Terrace A303

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $708 to $1,890/night

    Hoku'Ea Hale

    3 Bedrooms2.5 BathroomsSleeps 10
    2 nights minstay
    Hot Tub
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $693 to $945/night

    Hale Nanea

    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. $693 to $1,071/night

    Camp Magic 1

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Hot Tub
    FREE CANCELLATION
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $693 to $945/night

    Queens Bath Lookout

    5 BedroomsBathroomsSleeps 10
    3 nights minstay
    Pool
    FREE CANCELLATION
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $693 to $945/night

    Hale Lani

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $688 to $1,152/night

    Pu'uwai Hale

    4 BedroomsBathroomsSleeps 8
    3 nights minstay
  200. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations