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. $5,369/night

    Ocean Views from Heliconia 2302 Residences

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pool Hot Tub
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  5. $5,244/night

    Honua kai Konea 642/643 4 bedroom/4 bath

    4 BedroomsBathroomsSleeps 12
    3 nights minstay
    Pool Hot Tub
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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. $3,743 to $7,485/night

    Lani Kai

    4 BedroomsBathroomsSleeps 8
    3 nights minstay
    Hot Tub
    FREE CANCELLATION
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  11. $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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  13. $3,518/night

    Honua kai Konea 1024/1026 3 bedroom/3bath

    3 BedroomsBathroomsSleeps 10
    3 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. $3,141/night

    Maui Westside Properties- K501 Amazing 2 Bed

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
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  19. $2,852 to $3,743/night

    Dolphin House

    6 BedroomsBathroomsSleeps 10
    7 nights minstay
    FREE CANCELLATION
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  21. $2,732/night

    Maui Westside Properties: K301 Amazing 2 Bed W/BBQ

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
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  23. $2,495 to $4,990/night

    Hanalei Beachfront

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
  24. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  25. $2,495 to $2,673/night

    Kailua Beachside

    4 BedroomsBathroomsSleeps 14
    7 nights minstay
    Pool
    FREE CANCELLATION
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  27. $2,495 to $2,673/night

    Helen's Beach House

    6 BedroomsBathroomsSleeps 14
    7 nights minstay
    Pool
    FREE CANCELLATION
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  29. $2,210/night

    Maui Westside Properties- Honua Kai-H836

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  30. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  31. $2,041/night

    Maui Westside Properties: Honua kai- Konea 643

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
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  33. $2,041/night

    Maui Westside Properties: Honua Kai- Konea 642

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
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  35. $1,997/night

    Maui Westside Properties- Hokulani 306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
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  37. $1,995 to $3,392/night

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

    6 BedroomsBathroomsSleeps 16
    2 nights minstay
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $1,912/night

    Maui Westside Presents: Honua kai- Konea 1026

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
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  41. $1,900 to $2,138/night

    Makena Aloha Estate

    4 BedroomsBathroomsSleeps 10
    5 nights minstay
    Pool Hot Tub
  42. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  43. $1,871 to $2,339/night

    Pinetrees Beach Villa

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $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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  47. $1,782/night

    Hale Lani

    4 BedroomsBathroomsSleeps 14
    3 nights minstay
    Pool
    FREE CANCELLATION
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $1,695 to $3,743/night

    Hale Maluhia Hanalei

    1 Bedroom1.5  BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
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  51. $1,692 to $2,494/night

    Rainbow Hale Estate

    4 Bedrooms3.5 BathroomsSleeps 8
    5 nights minstay
    Pool
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $1,672 to $2,981/night

    Champion Ridge Home

    4 Bedrooms4.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
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  55. $1,651/night

    Maui Westside- Kaanapali Shores 259 Ocean Front!

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $1,605 to $5,291/night

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

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $1,559 to $3,431/night

    Ikena Lani

    5 BedroomsBathroomsSleeps 12
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $1,504/night

    Maui Westside- Presents- Honua kai- Konea 312

    2 Bedrooms BathroomSleeps 6
    3 nights minstay
    Pool Hot Tub
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  63. $1,497 to $2,139/night

    Laau Paina

    5 BedroomsBathroomsSleeps 10
    7 nights minstay
    FREE CANCELLATION
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $1,413 to $1,906/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. $1,374/night

    Maui Westside Properties- MAUI ELDORADO D200

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
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  71. $1,373 to $3,983/night

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

    4 Bedrooms4.5 BathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $1,372 to $2,246/night

    King Hale

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
    FREE CANCELLATION
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $1,352/night

    Maui Westside Properties Honua Kai- H712 XL

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $1,347/night

    Maui Westside:-Honua Kai- Hokulani 930

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $1,303 to $1,404/night

    Makalae

    5 BedroomsBathroomsSleeps 10
    3 nights minstay
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $1,245/night

    Maui Westside Properties- Hokulani 108 1 bedroom.

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $1,226 to $4,085/night

    4BD Estate Home at Puako Bay (74)

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $1,220 to $4,147/night

    3BD Villas at Mauna Kea #39

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $1,168/night

    Villa Cinco Resort at Kona Plantation Estates

    5 BedroomsBathroomsSleeps 15
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $1,136/night

    Maui Westside Presents: Honua kai- Konea 1024

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $1,094 to $1,413/night

    Moloa'a Bay Villa

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $1,076 to $3,399/night

    Turtle Bay Villas 216

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $1,076 to $1,909/night

    Wai'ula'ula #344

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $1,018 to $1,910/night

    Wai'ula'ula 318

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $998 to $1,996/night

    Kai Halulu

    3 Bedrooms3.5 BathroomsSleeps 7
    3 nights minstay
    Hot Tub
    FREE CANCELLATION
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $992 to $1,871/night

    Hale Naninoa

    5 BedroomsBathroomsSleeps 11
    3 nights minstay
    FREE CANCELLATION
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $909 to $4,314/night

    Maui Westside Properties- 3 Bed Penthouse K1019

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $899/night

    Kahana Outrigger #1A2

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool
    FREE CANCELLATION
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $899 to $1,434/night

    Hale Kauka

    3 Bedrooms2.5 BathroomsSleeps 7
    2 nights minstay
    Pool
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $870 to $1,401/night

    Whaler at Kaanapali Beach #852

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $870 to $1,401/night

    Whaler at Kaanapali Beach #402

    2 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. $813 to $1,438/night

    Kapalua Bay Villa 22G2 Gold Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $811 to $1,559/night

    Hanalei Beachfront Cottage

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    FREE CANCELLATION
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $811 to $1,871/night

    Mauna Pua- A 7 bedroom Kauai Vacation Rental

    7 BedroomsBathroomsSleeps 14
    3 nights minstay
    FREE CANCELLATION
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $811 to $1,871/night

    Hanalei Bluff

    3 Bedrooms3.5 BathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $781 to $1,406/night

    Kapalua Bay Villa 35B3 Gold Ocean Front

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $781 to $3,659/night

    MWP- Luana Garden Villa 3C

    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. $780 to $1,810/night

    Hokulani Villa

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $779 to $1,188/night

    Whaler at Kaanapali Beach #723

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $779 to $1,188/night

    Whaler at Kaanapali Beach #1173

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $775 to $1,790/night

    Hale Akala Falls Ko Olina Beach Villa (O121)

    3 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool Hot Tub
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $766 to $846/night

    Hale Honu-Oceanfront

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    Hot Tub
    FREE CANCELLATION
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $763 to $2,505/night

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

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $748 to $1,060/night

    Malapua

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $742 to $798/night

    Hale Mana

    4 BedroomsBathroomsSleeps 8
    7 nights minstay
    FREE CANCELLATION
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $740 to $2,016/night

    Hale Lalea Ko Olina Beach Villa (B310)

    2 BedroomsBathroomsSleeps 6
    6 nights minstay
    Pool Hot Tub
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $720 to $1,732/night

    Plantation Cottage at Poipu

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $720 to $1,226/night

    Mango Sunsets

    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. $719 to $1,137/night

    Island Time- Holua Kai

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $717 to $904/night

    Hale Koaniani

    3 Bedrooms2.5 BathroomsSleeps 6
    5 nights minstay
    FREE CANCELLATION
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $714 to $1,599/night

    Ohana Kamalani

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $696 to $829/night

    Whaler 859

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $688 to $1,152/night

    Pu'uwai Hale

    4 BedroomsBathroomsSleeps 8
    3 nights minstay
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $686 to $936/night

    Hale A Kai

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    FREE CANCELLATION
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $686 to $936/night

    Hale Nanea

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $686 to $936/night

    Hale Lani

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $686 to $936/night

    Queens Bath Lookout

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $679 to $761/night

    Grand Champions 124

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $674 to $811/night

    Kaanapali Shores 515

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $664/night

    White Sands Village#213

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $661 to $1,277/night

    Hale Anu Keanu

    4 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Hot Tub
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $661 to $1,018/night

    Blue Vacations Holua Kai

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $656 to $906/night

    Kapalua Bay Villa 21G4 Gold Beach Front

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $643 to $951/night

    Mahana 501

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $643 to $664/night

    Kapalua Bay Villas 17B-3

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $641 to $992/night

    Turtle Rock

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $631 to $1,150/night

    Koa Kai Hale

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $631 to $1,459/night

    Leilani Kai Hale

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $631 to $1,553/night

    Milo Hae Hale

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $625 to $2,579/night

    Kolea 6B at the Waikoloa Beach Resort

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $624 to $936/night

    Haena Kai

    3 BedroomsBathroomsSleeps 7
    2 nights minstay
    FREE CANCELLATION
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $623 to $3,349/night

    Honua kai Konea 312/314 3 bedroom/Two Bath

    3 BedroomsBathroomsSleeps 10
    1 night minstay
    Pool Hot Tub
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $619 to $678/night

    Mahana 1008

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $618 to $1,236/night

    Wai'ula'ula A102

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $614 to $655/night

    Kaanapali Royal H303

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