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. $220 to $580/night

    Kaanapali Royal #E302

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
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  3. $215 to $435/night

    Lahaina Shores #225

    Studio BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
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  5. $259 to $505/night

    Lahaina Shores #533

    Studio BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
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  7. $309 to $638/night

    Mahana Resort #1107

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
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  9. $145 to $249/night

    Pohailani #102

    Studio BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
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  11. $319 to $1,235/night

    Royal Kahana #1211

    2 Bedrooms2.5 BathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
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  13. $259 to $493/night

    Mahana Resort #813

    Studio BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
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  15. $309 to $640/night

    Lokelani #A205

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
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  17. $215 to $481/night

    Papakea #F105

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
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  19. $371/night

    Papakea #A201

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
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  21. $203 to $470/night

    Kaanapali Plantation #52

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
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  23. $176 to $447/night

    Lahaina Roads #204

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
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  25. $231 to $447/night

    Papakea #L207

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
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  27. $215 to $435/night

    Lahaina Shores #317

    Studio BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
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  29. $220 to $493/night

    Mahana Resort #1003

    Studio BathroomSleeps 3
    3 nights minstay
    Pool
    FREE CANCELLATION
  30. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  31. $303 to $766/night

    Kaanapali Plantation #28

    3 Bedrooms2.5 BathroomsSleeps 8
    3 nights minstay
    Pool
    FREE CANCELLATION
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  33. $214 to $238/night

    Puamana 25B

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
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  35. $220 to $238/night

    Hanalei Bay Resort 5201

    Studio BathroomSleeps 3
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  37. $214 to $238/night

    Cliffs 7303

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $322 to $383/night

    Villas of Kamalii 37

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  41. $202 to $246/night

    Kamahana 24

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
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  43. $159 to $182/night

    Sandpiper 120A

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $257 to $312/night

    Plantation at Princeville 1322

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  47. $397 to $458/night

    Puu Poa 405

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $238 to $275/night

    Sealodge F9

    1 Bedroom BathroomSleeps 3
    3 nights minstay
    Pool
    FREE CANCELLATION
  50. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  51. $268 to $361/night

    Hanalei Bay Villa 26

    2 Bedrooms2.5 BathroomsSleeps 4
    3 nights minstay
    FREE CANCELLATION
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $231 to $268/night

    Cliffs 5106

    1 BedroomBathroomsSleeps 2
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  54. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  55. $233 to $238/night

    Volcano Dancing Ferns Main House

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $250 to $900/night

    Fairway Villas L21 at the Waikoloa Beach Resort

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $119 to $438/night

    Marine Surf Waikiki 908

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $113 to $419/night

    Marine Surf Waikiki 2108

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $124 to $513/night

    Kona Magic Sands #111

    Studio BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $200 to $879/night

    Kona Reef #C32

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $200 to $915/night

    Kona Reef #D17

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $253 to $382/night

    KAMAOLE NALU, #104

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $328 to $484/night

    KAMAOLE NALU, #105

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $201 to $280/night

    KIHEI BEACH, #404

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $201 to $277/night

    KIHEI BEACH, #407

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $263 to $381/night

    KIHEI BEACH, #409

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $201 to $280/night

    KIHEI BEACH, #107

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $201 to $280/night

    KIHEI BEACH, #307

    1 BedroomBathroomsSleeps 2
    5 nights minstay
    Pool
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $201 to $358/night

    SUGAR BEACH RESORT, #329

    1 Bedroom BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $201 to $348/night

    SUGAR BEACH RESORT, #518^

    1 Bedroom BathroomSleeps 2
    7 nights minstay
    Pool Hot Tub
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $312 to $369/night

    ROYAL MAUIAN, #208^

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $577 to $679/night

    MENEHUNE SHORES, #510**^

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $201 to $277/night

    KIHEI BEACH, #405

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $287 to $383/night

    Wailea Ekahi, #33B

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $201 to $280/night

    KIHEI BEACH, #603^

    1 Bedroom BathroomSleeps 3
    5 nights minstay
    Pool
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $291 to $414/night

    KIHEI BEACH, #501

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $428 to $484/night

    Kahana Sunset F4

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $172 to $220/night

    Pohailani 128

    1 Bedroom BathroomSleeps 5
    5 nights minstay
    Pool
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $226 to $321/night

    Papakea A309

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $1,900 to $2,138/night

    Makena Aloha Estate

    4 BedroomsBathroomsSleeps 10
    5 nights minstay
    Pool Hot Tub
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $208 to $315/night

    Papakea J103

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $505 to $564/night

    Papakea A404

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool Hot Tub
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $708 to $1,890/night

    Hoku'Ea Hale

    3 Bedrooms2.5 BathroomsSleeps 10
    2 nights minstay
    Hot Tub
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $599 to $1,146/night

    Piko Nani

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $423 to $854/night

    Kona Nalu 304

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $487 to $1,175/night

    Kahalu'u Hale

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $363 to $826/night

    Iki Nui Hale

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $396 to $780/night

    Ocean Soul (Big Island)

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $417 to $1,077/night

    Kiahuna Lani at Poipu

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $243 to $615/night

    Poipu Crater

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $348 to $932/night

    Honl's Beach Hale (Big Island)

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Hot Tub
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $583 to $1,654/night

    Hokulani Villa

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $10,240 to $12,620/night

    Mauna Kea Bluffs #5: La Ikena O Komohana*

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $2,203 to $3,457/night

    4BD Villas at Mauna Kea #21

    4 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $265 to $542/night

    Kahikole

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $480 to $1,553/night

    Milo Hae Hale

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $262 to $536/night

    Keauhou Surf & Racquet 58

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $221 to $580/night

    Aina Nalu B106- Extremely Rare Unit

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $1,220 to $4,070/night

    3BD Villas at Mauna Kea #39

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $750 to $2,505/night

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

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $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
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $396 to $923/night

    Pili Mai 8D

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $455 to $1,132/night

    Hale Kanani (Kaua'i) TVNC 1342

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $265 to $478/night

    Hale Oliveira

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $1,404 to $4,289/night

    Lau'lea at the Mauna Lani*

    4 Bedrooms4.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $262 to $530/night

    Kona Plaza 314

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $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
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $279 to $580/night

    Lai Nani Oceanfront Estate Bungalow #1

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $423 to $887/night

    Palm Villas (H23) at Mauna Lani 2 Bedrooms + Loft

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $833 to $2,743/night

    Ali'i Villa

    4 Bedrooms4.5 BathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $250 to $661/night

    Mauna Lani Golf Villas Q2

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $423 to $1,103/night

    Kanaloa at Kona 3304

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $288 to $699/night

    Mauna Kai 2

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $333 to $393/night

    Song of the Ocean

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $221 to $580/night

    *NEW* Aina Nalu B105: Ground Floor, Quiet Condo in Livel...

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $213 to $714/night

    Maui Lani Terraces A205

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $417 to $1,081/night

    Hallor House TVNC #5147

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $833 to $2,478/night

    Ke Kailani Hale A2

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $262 to $492/night

    Casa De Emdeko 222

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $333 to $791/night

    Casa De Emdeko 336

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $268 to $593/night

    Casa de Emdeko 337

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $274 to $619/night

    Casa De Emdeko 235

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $286 to $536/night

    Kona Alii 304

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $387 to $781/night

    The Cottage

    1 Bedroom BathroomSleeps 4
    2 nights minstay
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $1,250 to $3,224/night

    Ali'i Point

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $417 to $1,081/night

    Hale Waileia

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $1,196 to $2,743/night

    Wai'ulu Villa 115D

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool
  200. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations