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. $17,250 to $26,450/night

    Kauhale Pilialoha

    10 Bedrooms14 BathroomsSleeps 30
    6 nights minstay
    Pool Hot Tub
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  3. $9,775 to $11,500/night

    Western Sunview

    5 BedroomsBathroomsSleeps 10
    5 nights minstay
    Pool
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  5. $3,780 to $7,560/night

    Lani Kai

    4 BedroomsBathroomsSleeps 8
    4 nights minstay
    Hot Tub
    FREE CANCELLATION
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  7. $2,336 to $5,088/night

    Hale Nui

    5 Bedrooms5.5 BathroomsSleeps 10
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  9. $2,141 to $3,780/night

    Napili Ocean Front House 43

    5 BedroomsBathroomsSleeps 10
    5 nights minstay
    Hot Tub
    FREE CANCELLATION
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  11. $1,900 to $2,969/night

    Makena Aloha Estate

    4 BedroomsBathroomsSleeps 10
    5 nights minstay
    Pool Hot Tub
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  13. $1,890 to $3,780/night

    Hale Maluhia Hanalei

    1 Bedroom1.5  BathroomSleeps 4
    4 nights minstay
    FREE CANCELLATION
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  15. $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
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  17. $1,890 to $2,520/night

    Helen's Beach House

    6 BedroomsBathroomsSleeps 14
    7 nights minstay
    Pool
    FREE CANCELLATION
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  19. $1,890/night

    Kailua Beachside

    4 BedroomsBathroomsSleeps 14
    7 nights minstay
    Pool
    FREE CANCELLATION
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  21. $1,870 to $2,494/night

    Wilikoki House

    6 BedroomsBathroomsSleeps 10
    5 nights minstay
    FREE CANCELLATION
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  23. $1,733 to $3,812/night

    Ikena Lani

    5 BedroomsBathroomsSleeps 12
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  25. $1,692 to $2,494/night

    Rainbow Hale Estate

    4 Bedrooms3.5 BathroomsSleeps 8
    5 nights minstay
    Pool
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  27. $1,265 to $2,760/night

    Hale Keanu

    4 Bedrooms4.5 BathroomsSleeps 9
    5 nights minstay
    Pool Hot Tub
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  29. $1,260 to $1,531/night

    Hale Maluhia Waialua

    3 Bedrooms3.5 BathroomsSleeps 8
    7 nights minstay
    FREE CANCELLATION
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  31. $1,224 to $1,698/night

    Kaanapali Alii 456

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  33. $1,193 to $1,312/night

    2 Charming Cottages on the Ocean

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    FREE CANCELLATION
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  35. $1,134 to $1,890/night

    Hale Hoku

    5 BedroomsBathroomsSleeps 12
    3 nights minstay
    FREE CANCELLATION
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  37. $1,132 to $1,168/night

    Villa Cinco Resort at Kona Plantation Estates

    5 BedroomsBathroomsSleeps 15
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $1,121 to $1,531/night

    Hale Lani

    4 BedroomsBathroomsSleeps 14
    2 nights minstay
    Pool
    FREE CANCELLATION
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  41. $1,071 to $1,404/night

    Makalae

    5 BedroomsBathroomsSleeps 10
    3 nights minstay
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  43. $1,009 to $1,732/night

    Moloa'a Bay Villa and Cottage

    5 BedroomsBathroomsSleeps 12
    3 nights minstay
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $1,008 to $2,016/night

    Kai Halulu

    3 Bedrooms3.5 BathroomsSleeps 7
    4 nights minstay
    Hot Tub
    FREE CANCELLATION
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  47. $938 to $1,372/night

    Hale Ola Kai

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $905 to $995/night

    Idyllic 1BR Oceanfront Cottage

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    FREE CANCELLATION
  50. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  51. $833 to $1,738/night

    Hale Lalea Ko Olina Beach Villa (B310)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
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  53. $819 to $1,254/night

    Hanalei Beachfront Cottage

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    FREE CANCELLATION
  54. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  55. $819 to $1,890/night

    Mauna Pua- A 7 bedroom Kauai Vacation Rental

    7 BedroomsBathroomsSleeps 14
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $766 to $846/night

    Hale Honu-Oceanfront

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    Hot Tub
    FREE CANCELLATION
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $759/night

    Mauna Lani Terrace D201

    2 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $750 to $806/night

    Hale Mana

    4 BedroomsBathroomsSleeps 8
    7 nights minstay
    FREE CANCELLATION
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  63. $748 to $1,060/night

    Malapua

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $745 to $1,619/night

    Hale Pumehana Ko Olina Beach Villa (O1202)

    3 Bedrooms2.5 BathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $745 to $1,619/night

    Hale Akala Falls Ko Olina Beach Villa (O121)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $728 to $1,152/night

    Pu'uwai Hale

    4 BedroomsBathroomsSleeps 8
    3 nights minstay
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $725 to $1,884/night

    Punahele

    3 Bedrooms2.5 BathroomsSleeps 8
    3 nights minstay
    Hot Tub
    FREE CANCELLATION
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $717 to $904/night

    Hale Koaniani

    3 Bedrooms2.5 BathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $711 to $775/night

    Punahele Point

    3 Bedrooms3.5 BathroomsSleeps 10
    3 nights minstay
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  77. $693 to $945/night

    Hale Nanea

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $693 to $945/night

    Hale Lani

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $686 to $873/night

    Lokelani Hale

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $686 to $936/night

    Hale A Kai

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    FREE CANCELLATION
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $667 to $1,610/night

    Keauhou Elima

    3 Bedrooms5.5 BathroomsSleeps 10
    5 nights minstay
    Pool
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $642 to $759/night

    Kona Bubbles

    4 Bedrooms4.5 BathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $641 to $992/night

    Turtle Rock

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $630 to $945/night

    Haena Kai

    3 BedroomsBathroomsSleeps 7
    3 nights minstay
    FREE CANCELLATION
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $623 to $748/night

    Hale Kalani

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    FREE CANCELLATION
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $618 to $1,236/night

    Wai'ula'ula A102

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $608 to $790/night

    Hale Huna Kai- Oceanfront

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    FREE CANCELLATION
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $608 to $791/night

    Alii Point #15- Almost Oceanfront

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $608 to $846/night

    Alii Point #7 Oceanfront

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $590 to $893/night

    Sands of Kahana 282

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $585 to $1,693/night

    Hale Papakea Ko Olina Beach Villa (B110)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $585 to $1,693/night

    Hale Nani Ikena Kai Ko Olina Beach Villa (B109)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $584 to $773/night

    Keauhou Kona Surf and Racquet Club 5-304

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $583 to $584/night

    Ono Hale

    3 Bedrooms2.5 BathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $571 to $584/night

    Koana Breeze

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $571 to $1,259/night

    Hale Leilani Ko Olina Beach Villa (B708)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $565 to $1,141/night

    Mahana 519

    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. $563 to $1,044/night

    Kaanapali Shores 403

    2 BedroomsBathroomsSleeps 7
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $557 to $619/night

    Sands of Kahana 366

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $557 to $619/night

    Sands Of Kahana 474

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $555 to $576/night

    Hale Pahukoa

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $549 to $801/night

    Kaanapali Shores 103

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $549 to $1,150/night

    Mahana 501

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $548 to $657/night

    2 Bedrooms Oceanfront

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $536 to $1,890/night

    Mauna Pua- A Four Bedroom Vacation Rental Home

    4 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $536 to $1,449/night

    Coral Hale

    5 BedroomsBathroomsSleeps 10
    3 nights minstay
    Hot Tub
    FREE CANCELLATION
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $533 to $711/night

    Papakea L405

    2 BedroomsBathroomsSleeps 7
    5 nights minstay
    Pool Hot Tub
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $533 to $711/night

    Papakea A404

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool Hot Tub
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $529 to $1,548/night

    Hale Kai Ko Olina Beach Villa (B904)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $525 to $1,205/night

    Wai'ula'ula A202

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $520 to $581/night

    Hanalei Bay Resort 52012

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $519 to $817/night

    ‘Aniani Hale’- The Glass House- Views, Pool, Spa

    4 Bedrooms4.5 BathroomsSleeps 8
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $513 to $924/night

    Noelani 304 3bdrm 2.5 bath

    3 Bedrooms2.5 BathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $513/night

    Hale Kai 2 Ko Olina Beach Villa (B906)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $512 to $1,498/night

    Hale Ohana Ko Olina Beach Villa (B801)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $506 to $563/night

    Sands Of Kahana 234

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $506 to $563/night

    Sands Of Kahana 215

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $506 to $563/night

    Sands Of Kahana 272

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $502 to $796/night

    Pair of 2BR Hawaiian Cottages

    4 BedroomsBathroomsSleeps 8
    7 nights minstay
    FREE CANCELLATION
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $501 to $557/night

    Sands Of Kahana 275

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $501 to $557/night

    Sands Of Kahana 356

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $500 to $860/night

    Papakea K-402

    3 Bedrooms2.5 BathroomsSleeps 8
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $499 to $562/night

    Ohana House

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $496/night

    Casa De Emdeko 219

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $494 to $1,196/night

    Sands of Kahana 354

    2 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $493 to $1,174/night

    Wai'ula'ula D201

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $487 to $770/night

    Noelani 401 OF 1 Bdm/2 Ba

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $486 to $1,403/night

    Hale Uliuli Lani Ko Olina Beach Villa (O1602)

    3 Bedrooms2.5 BathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $486 to $608/night

    Kona Bay Seaclusion-Oceanfront

    2 Bedrooms2.5 BathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $485 to $604/night

    Waipouli Beach Resort G-404

    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. $484/night

    Kahana Sunset F1

    2 Bedrooms2.5 BathroomsSleeps 6
    14 nights minstay
    Pool
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $481 to $734/night

    Mahana 1008

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $481 to $962/night

    Honua Kai Konea 743 2BD 2BA

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $481 to $896/night

    Ainamalu 29 at Waikoloa Beach Resort

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $474 to $577/night

    Maui Eldorado I204/205 2Bd/ 2Ba

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $473 to $547/night

    Regency at Poipu Kai #721

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $472 to $1,355/night

    Hale Ka Wailele Malu Ko Olina Beach Villa (O226)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $472 to $924/night

    Papakea H404

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