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. $4,194/night

    Kalina at Hapuna Beach

    4 Bedrooms4.5 BathroomsSleeps 10
    5 nights minstay
    Pool Hot Tub
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  5. $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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  7. $1,797 to $2,217/night

    Hale Waiulu

    3 Bedrooms3.5 BathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
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  9. $1,761 to $2,076/night

    WAILEA ELUA, #1305^

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool Hot Tub
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  11. $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
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  13. $1,613 to $3,219/night

    Hillside Villa 7101

    3 Bedrooms BathroomSleeps 6
    2 nights minstay
    Pool
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  15. $1,605 to $4,612/night

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

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
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  17. $1,553 to $3,398/night

    Laulea Kailani Villa (KAUAI)

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool
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  19. $1,373 to $3,476/night

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

    4 Bedrooms4.5 BathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
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  21. $1,318 to $2,876/night

    Hale Keanu

    4 Bedrooms4.5 BathroomsSleeps 9
    5 nights minstay
    Pool Hot Tub
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  23. $1,303 to $1,404/night

    Makalae

    5 BedroomsBathroomsSleeps 10
    3 nights minstay
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  25. $1,250 to $3,227/night

    Ali'i Point

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  26. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  27. $1,220 to $3,619/night

    3BD Villas at Mauna Kea #39

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
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  29. $1,195 to $3,675/night

    Turtle Bay Villas 216

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
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  31. $1,168/night

    Villa Cinco Resort at Kona Plantation Estates

    5 BedroomsBathroomsSleeps 15
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  32. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  33. $1,166 to $2,743/night

    Fairway Villa 104A

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
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  35. $1,059 to $1,553/night

    Villages at Mauna Lani Resort Unit # 728

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
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  37. $1,056 to $3,093/night

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

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $1,013 to $2,950/night

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

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
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  41. $1,009 to $1,572/night

    WAILEA ELUA, #1403

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
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  43. $899 to $2,294/night

    Mana Alana at Poipu

    3 Bedrooms3.5 BathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $897 to $1,459/night

    WAILEA ELUA, #1204^

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
  46. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  47. $897 to $1,572/night

    WAILEA ELUA, #1002

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $897 to $1,459/night

    WAILEA ELUA, #1702

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
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  51. $893 to $2,380/night

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

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
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  53. $855 to $1,319/night

    MAKENA SURF RESORT, #B-204

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  54. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  55. $855 to $1,319/night

    MAKENA SURF RESORT, #E-205

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $813 to $1,438/night

    Kapalua Bay Villa 22G2 Gold Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $781 to $1,406/night

    Kapalua Bay Villa 35B3 Gold Ocean Front

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $781 to $1,406/night

    Kapalua Bay Villa 34B2 Gold Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $781 to $1,438/night

    Kapalua Bay Villa 20G2 Gold Beach Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $780 to $1,718/night

    Hale Emmalani

    4 Bedrooms3.5 BathroomsSleeps 11
    2 nights minstay
    Hot Tub
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $775 to $1,094/night

    MAKENA SURF RESORT, #G-201*

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $775 to $1,094/night

    MAKENA SURF RESORT, #G-101

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $775 to $1,094/night

    MAKENA SURF RESORT, #G-104

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $760 to $1,952/night

    Mauna Lani KaMilo Home (349)

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $759/night

    Mauna Lani Terrace D201

    2 Bedrooms2.5 BathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $749 to $1,871/night

    Hanalei Bay View

    4 BedroomsBathroomsSleeps 12
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $724 to $1,065/night

    Wailea Elua, #0908

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $724 to $1,065/night

    WAILEA ELUA, #2204*

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $724 to $1,065/night

    WAILEA ELUA, #2304

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $720 to $1,732/night

    Plantation Cottage at Poipu

    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. $718 to $3,659/night

    MWP- Luana Garden Villa 3C

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $706 to $1,038/night

    MAKENA SURF RESORT, #C-106

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $706 to $1,038/night

    MAKENA SURF RESORT, #C-102

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $706 to $1,038/night

    MAKENA SURF RESORT, #C-103

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $688 to $1,152/night

    Pu'uwai Hale

    4 BedroomsBathroomsSleeps 8
    3 nights minstay
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $686 to $936/night

    Hale Nanea

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $686 to $936/night

    Hale Lani

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $668/night

    Ali'i Point #5 Oceanfront

    3 Bedrooms3.5 BathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $656 to $906/night

    Kapalua Bay Villa 21G4 Gold Beach Front

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $634 to $896/night

    WAILEA ELUA, #1309

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $631 to $1,553/night

    Milo Hae Hale

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $619 to $869/night

    Kapalua Bay Villa 22G4 Gold Ocean Front

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $618 to $1,236/night

    Wai'ula'ula A102

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $613 to $1,668/night

    Hale Pumehana Ko Olina Beach Villa (O1202)

    3 Bedrooms2.5 BathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $608/night

    Alii Point #15- Almost Oceanfront

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $601 to $663/night

    Hanalei Bay Resort 52012

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $584/night

    Keauhou Kona Surf and Racquet Club 5-304

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $584/night

    Ono Hale

    3 Bedrooms2.5 BathroomsSleeps 8
    4 nights minstay
    Pool
    FREE CANCELLATION
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $581 to $1,106/night

    Kapalua Bay Villa 23B3 Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $576/night

    Hale Pahukoa

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool
    FREE CANCELLATION
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $571 to $1,784/night

    Hale Kai Ko Olina Beach Villa (B904)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $571 to $1,065/night

    WAILEA ELUA, #0902

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $571 to $1,065/night

    WAILEA ELUA, #0202*

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $565 to $2,671/night

    Maui Westside Properties- Honua Kai- Hokulani 509

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $563 to $781/night

    Kapalua Bay Villa 36B3 Gold Ocean Front

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $563 to $1,156/night

    Kapalua Bay Villa 29B2 Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $552 to $957/night

    Hali'i Kai 12E

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $552 to $1,532/night

    Laulea Hale

    4 BedroomsBathroomsSleeps 12
    2 nights minstay
    FREE CANCELLATION
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $549/night

    Kona Makai 1-301

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $548 to $2,016/night

    Hale Papakea Ko Olina Beach Villa (B110)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $544 to $1,119/night

    Kapalua Bay Villa 31G4 Gold Ocean View

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $544 to $1,119/night

    Kapalua Bay Villa 32B2 Gold Ocean View

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $542 to $1,117/night

    Kiahuna Plantation Hale

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $542 to $1,137/night

    Awapuhi Hale

    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. $542 to $1,117/night

    Kiahuna Lani at Poipu

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $542 to $1,183/night

    Hale Waileia

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $530 to $1,435/night

    Coral Hale

    5 BedroomsBathroomsSleeps 10
    3 nights minstay
    Hot Tub
    FREE CANCELLATION
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $530 to $1,871/night

    Mauna Pua- A Four Bedroom Vacation Rental Home

    4 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $526 to $860/night

    Papakea K-402

    3 Bedrooms2.5 BathroomsSleeps 8
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $525 to $1,205/night

    Wai'ula'ula A202

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $513 to $962/night

    Honua Kai Konea 743 2BD 2BA

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $512 to $1,007/night

    Pili Mai 8D

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $505 to $564/night

    Papakea A404

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool Hot Tub
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $504 to $896/night

    WAILEA ELUA, #1402^

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $504 to $896/night

    WAILEA ELUA, #1601

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $496/night

    Casa De Emdeko 219

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $493 to $1,174/night

    Wai'ula'ula D201

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $482 to $1,025/night

    Pili Mai 6K

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $482 to $868/night

    WAILEA ELUA, #0302

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $481 to $1,031/night

    Kapalua Ridge Villa 1214 Gold Ocean View

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $478 to $1,268/night

    Hale Moana Ko Olina Beach Villa (B305)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $478/night

    Kona Coast Resort at Keauhou Gardens 8204

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $476 to $908/night

    Pili Mai 11I

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $474 to $564/night

    Papakea L405

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $470 to $953/night

    WAILEA ELUA, #1503

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $470 to $953/night

    WAILEA ELUA, #0307

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $470 to $953/night

    WAILEA ELUA, #0801*

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