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. $8,071/night

    Hanalei Dream

    5 BedroomsBathroomsSleeps 14
    7 nights minstay
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  3. $4,882 to $6,780/night

    Hanalei Beach Estate

    5 Bedrooms5.5 BathroomsSleeps 13
    3 nights minstay
    Hot Tub
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  5. $4,200/night

    Timeshare Condo

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
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  7. $3,570 to $7,910/night

    Haena Modern Beachfront Sleeps 12

    6 BedroomsBathroomsSleeps 12
    2 nights minstay
    Hot Tub
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  9. $3,461 to $13,023/night

    Wailea Beach Villa B202

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  11. $3,221 to $5,085/night

    Turtle Cove

    3 Bedrooms3.5 BathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
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  13. $3,106 to $10,727/night

    Andaz Villa 810

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  15. $3,051 to $3,949/night

    Napili Ocean Front House 43

    5 BedroomsBathroomsSleeps 10
    1 night minstay
    Hot Tub
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  17. $2,884 to $12,552/night

    Wailea Beach Villa B102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  19. $2,712 to $3,955/night

    Makana Nui

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
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  21. $2,702 to $3,365/night

    WAILEA ELUA, #1305^

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  23. $2,260 to $5,115/night

    Hanalei Beachfront Hale

    3 Bedrooms3.5 BathroomsSleeps 8
    4 nights minstay
    Hot Tub
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  25. $2,131 to $2,855/night

    MAKENA SURF, #G-301-302

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  26. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  27. $2,000 to $5,198/night

    Gorgeous Renovated 1937 Plantation Style Beach House 50 ...

    5 BedroomsBathroomsSleeps 10
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  28. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  29. $1,950 to $2,249/night

    Puuwai Alii Estate

    5 Bedrooms5.5 BathroomsSleeps 8
    7 nights minstay
  30. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  31. $1,846 to $6,188/night

    Halama Hale Private Home

    4 Bedrooms3.5 BathroomsSleeps 14
    2 nights minstay
    Pool
    FREE CANCELLATION
  32. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  33. $1,730 to $5,160/night

    The Cove Hale

    4 BedroomsBathroomsSleeps 18
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  35. $1,695 to $2,260/night

    Makana Pool House

    5 BedroomsBathroomsSleeps 10
    5 nights minstay
    Pool Hot Tub
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  37. $1,695 to $2,260/night

    Huaka Mahina

    4 Bedrooms4.5 BathroomsSleeps 8
    5 nights minstay
    Pool
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $1,695 to $2,712/night

    Hale Hoku

    5 BedroomsBathroomsSleeps 12
    3 nights minstay
  40. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  41. $1,604 to $2,164/night

    Moloa'a Bay Villa & Cottage

    5 BedroomsBathroomsSleeps 11
    3 nights minstay
  42. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  43. $1,413 to $2,726/night

    Haena Modern Beachfront Hale Ekahi

    3 Bedrooms2.5 BathroomsSleeps 6
    3 nights minstay
    Hot Tub
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  45. $1,373 to $2,543/night

    Haena Beach House

    2 Bedrooms1.5  BathroomSleeps 4
    2 nights minstay
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  47. $1,356 to $2,874/night

    Hanalei Zen Retreat

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
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  49. $1,355 to $1,801/night

    Hale Ona Loa

    4 BedroomsBathroomsSleeps 8
    7 nights minstay
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  51. $1,349 to $1,609/night

    Moloa'a Bay Villa

    3 BedroomsBathroomsSleeps 7
    3 nights minstay
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  53. $1,325 to $1,784/night

    MAKENA SURF #G101

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  54. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  55. $1,309 to $3,390/night

    Hale Hanalei

    5 BedroomsBathroomsSleeps 10
    4 nights minstay
    Hot Tub
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  57. $1,276 to $2,356/night

    Haena Modern Beachfront Hale Elua

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $1,243 to $2,994/night

    Bond House

    4 BedroomsBathroomsSleeps 10
    5 nights minstay
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $1,223 to $1,427/night

    POLO BEACH CLUB #707

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $1,220 to $4,333/night

    Big Island Hale Kaheka 6592

    1 Bedroom2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  65. $1,212 to $4,510/night

    Wailea Elua 1603

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $1,202 to $1,459/night

    Luxury Makalae Home close to Water Activities

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $1,180 to $1,752/night

    Makana Akua Haena

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $1,175 to $3,040/night

    Hale Naninoa

    5 BedroomsBathroomsSleeps 11
    3 nights minstay
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $1,172 to $1,937/night

    WAILEA ELUA, #1403

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $1,155 to $1,680/night

    Turtle Rock

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $1,154 to $5,643/night

    Wailea Beach Villa M312

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $1,152 to $5,494/night

    Ho'olei 17-1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $1,130 to $1,208/night

    Blue Mahina at Sunset Beach

    4 BedroomsBathroomsSleeps 11
    7 nights minstay
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $1,126 to $4,089/night

    Big Island Hualalai 133C

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $1,119 to $2,716/night

    Tradewinds

    5 BedroomsBathroomsSleeps 10
    3 nights minstay
    Pool Hot Tub
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $1,096 to $5,256/night

    Wailea Beach Villa I503

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $1,080 to $1,835/night

    WAILEA ELUA, #1404

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $1,080 to $1,835/night

    WAILEA ELUA, #1702

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $1,080 to $1,835/night

    WAILEA ELUA, #1204

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $1,074 to $2,091/night

    Kai Halulu

    3 Bedrooms3.5 BathroomsSleeps 7
    5 nights minstay
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $1,074 to $2,081/night

    Spindrift Kauai

    3 Bedrooms3.5 BathroomsSleeps 6
    5 nights minstay
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $1,068 to $2,825/night

    King Hale

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $1,038 to $4,454/night

    Ho'olei 112-5

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $1,038 to $3,989/night

    Wailea Beach Villa H202

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $1,038 to $5,154/night

    Ho'olei 17-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $1,020 to $1,458/night

    MAKENA SURF, #G-304

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $1,017 to $3,012/night

    Anahola Aloha Beach House

    4 BedroomsBathroomsSleeps 12
    3 nights minstay
    Hot Tub
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $1,017 to $2,208/night

    Hanalei Beachfront Cottage

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
    Hot Tub
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $998 to $1,567/night

    Kahana Outrigger #1A2

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $991 to $2,056/night

    Hale Kalani

    2 Bedrooms1.5  BathroomSleeps 4
    5 nights minstay
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $989 to $2,788/night

    Honua Kai Konea 250

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $987 to $4,656/night

    Ho'olei 39-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $981 to $4,456/night

    Ho'olei 21-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $961 to $1,108/night

    Pu'uwai Hale

    4 Bedrooms4.5 BathroomsSleeps 8
    3 nights minstay
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $961 to $1,695/night

    Punahele

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    Hot Tub
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $942 to $1,055/night

    Sea Turtle Ranch

    4 BedroomsBathroomsSleeps 8
    30 nights minstay
    Hot Tub
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $937 to $1,611/night

    MAKENA SURF, #F-209

    2 BedroomsBathroomsSleeps 4
    7 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $937 to $1,611/night

    MAKENA SURF, #F-212

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $937 to $1,611/night

    MAKENA SURF, #F-110

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $937 to $1,611/night

    MAKENA SURF #F-102

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $937 to $1,560/night

    MAKENA SURF #B304

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $937 to $1,560/night

    MAKENA SURF, #E-202

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $936 to $2,309/night

    Mauna Pua- A 7 bedroom Kauai Vacation Rental

    7 BedroomsBathroomsSleeps 14
    2 nights minstay
    Hot Tub
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $935 to $1,860/night

    Big Island Private Home Alii Drive 6596

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $923 to $4,577/night

    Ho'olei 24-4

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $923 to $3,773/night

    Ho'olei 55-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $923 to $2,661/night

    Big Island Holua Kai 7061

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $923 to $4,201/night

    Ho'olei 24-1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $922 to $3,285/night

    Maui Dolphin House

    4 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $921 to $4,329/night

    Ho'olei 55-2

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $904 to $2,387/night

    Camp Magic 1

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Hot Tub
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $904 to $1,017/night

    Kumulani

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $904 to $1,243/night

    Haena Kai

    3 BedroomsBathroomsSleeps 7
    3 nights minstay
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $898 to $2,261/night

    Niulani Lanikai- Kauai Beach House

    4 BedroomsBathroomsSleeps 10
    3 nights minstay
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $896 to $1,456/night

    HOKUEA HALE

    3 Bedrooms2.5 BathroomsSleeps 10
    3 nights minstay
    Hot Tub
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $886 to $3,059/night

    Aloha 'Ohana

    5 BedroomsBathroomsSleeps 12
    4 nights minstay
    Pool
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $866 to $1,535/night

    Kahana Outrigger #2B1

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $866 to $3,968/night

    Ho'olei 24-6

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $865 to $3,917/night

    Ho'olei 12-4

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $848 to $1,835/night

    Hale Ohana Nui

    5 Bedrooms6.5 BathroomsSleeps 12
    3 nights minstay
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $839 to $1,575/night

    Holua House#28

    3 Bedrooms3.5 BathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $837 to $1,392/night

    Kapalua Ridge Villas-#323

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $835 to $1,325/night

    MAKENA SURF #C102

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $835 to $1,325/night

    MAKENA SURF, #C-106

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $835 to $1,611/night

    MAKENA SURF, #G-104

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $825 to $1,320/night

    Ali'i Point #5 Oceanfront

    3 Bedrooms3.5 BathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $824 to $1,045/night

    Hale Honu-Oceanfront

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    Hot Tub
    FREE CANCELLATION
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $815 to $1,529/night

    Wailea Elua, #0908

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $815 to $1,529/night

    WAILEA ELUA, #2304

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $815 to $1,529/night

    WAILEA ELUA, #0702

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $808 to $3,059/night

    Wailea Beach Villa J106

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $802 to $3,899/night

    Ho'olei 24-2

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