RedAwning has over 350 Maui vacation homes and condos which all include instant online booking and no security deposits, to make your trip easy and stress-free. Maui is home to some of Hawaii’s most beautiful beaches and offers plenty of opportunities for adventure, from snorkeling with turtles to hiking through the bamboo forest to cliff diving in Hana. Book your stay today!

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  1. $270 to $499/night

    Kahana Sunset B7

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool
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  3. $365 to $730/night

    Napili Point C12 2 Bedroom Condo

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
    FREE CANCELLATION
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  5. $184 to $323/night

    Kuleana 622 1 Bedroom Condo

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
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  7. $430 to $897/night

    Sands of Kahana 282 2 Bedroom Condo

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  9. $325 to $686/night

    Napili Shores A106 Studio Condo

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
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  11. $222 to $493/night

    Kaleialoha 106 1 Bedroom Condo

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
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  13. $644 to $2,018/night

    Sands Of Kahana PH 381 3Bd/3Ba OF

    3 BedroomsBathroomsSleeps 10
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
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  15. $512 to $1,017/night

    Honua Kai 215 2 Bed/2 Bath

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
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  17. $205 to $493/night

    Napili Point B33 1 Bedroom Oceanfront Condo

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
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  19. $325 to $686/night

    Napili Shores A202 OF Studio

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
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  21. $384 to $826/night

    Kahana Village 40 Oceanfront 2Bed/2Bath

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
    FREE CANCELLATION
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  23. $469 to $1,006/night

    Kahana Village 13 Oceanview 3Bed/2Bath

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool
    FREE CANCELLATION
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  25. $148 to $352/night

    Valley Isle #905

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  27. $394 to $735/night

    Hale Mahina #B403

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  29. $291 to $516/night

    Royal Kahana #209

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  31. $473 to $590/night

    Kaanapali Shores #159

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
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  33. $629 to $972/night

    Kaanapali Shores #255

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
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  35. $532 to $840/night

    The Mahana #1204

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
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  37. $247 to $502/night

    The Mahana #518

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
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  39. $302 to $603/night

    The Mahana #906

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
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  41. $415 to $893/night

    Maui Kaanapali Villas #A317

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  43. $198 to $532/night

    Maui Kaanapali Villas #E290

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $415 to $515/night

    Maui Kaanapali Villas #A517

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  46. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  47. $210 to $453/night

    Maui Sands #5G

    2 Bedrooms1.5  BathroomSleeps 5
    2 nights minstay
    FREE CANCELLATION
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  49. $193 to $417/night

    Kahana Reef #116

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  51. $209 to $402/night

    Kahana Reef #301

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  53. $236 to $314/night

    Kahana Reef #211

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  55. $185 to $365/night

    Kahana Reef #414

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $341 to $586/night

    Papakea #E207

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $373 to $641/night

    Papakea #G103

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $231 to $405/night

    Pohailani #102

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $219 to $612/night

    Kaanapali Plantation #52

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    FREE CANCELLATION
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  65. $273 to $511/night

    Kahana Reef #310

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $446 to $893/night

    Maui Kaanapali Villas #A512

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $394 to $720/night

    Papakea #F407

    2 Bedrooms BathroomSleeps 6
    2 nights minstay
    FREE CANCELLATION
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $210 to $392/night

    Maui Sands #6E

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    FREE CANCELLATION
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  73. $315 to $586/night

    Paki Maui #103

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $233 to $499/night

    Mahana At Kaanapali 306

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $231 to $447/night

    Pohailani #201

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $263 to $622/night

    Maui Kaanapali Villas #B247

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $252 to $473/night

    Kahana Sunset B3

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $185 to $433/night

    Kaleialoha 209 1 Bedroom Condo

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $161 to $373/night

    Kaanapali Shores 642 Studio Condo

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $261 to $630/night

    Maui Kai 908 Oceanfront 1 Bedroom

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $406 to $620/night

    Luana Kai C-301

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $254 to $752/night

    Sugar Beach Resort 209

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $312 to $1,044/night

    Kamaole Nalu 103

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $318 to $1,335/night

    Wailea Ekahi 25B

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $143 to $404/night

    Kahana Sunset B3B

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $238 to $446/night

    Kahana Sunset D10

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $233 to $499/night

    Kahana Sunset D8

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $222 to $446/night

    Sands Of Kahana 231

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $233 to $499/night

    Kahana Sunset D2

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $528 to $1,129/night

    Sands Of Kahana 474

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $205 to $415/night

    Ridge Villa 1422

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $216 to $331/night

    Valley Isle Resort 310

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $230 to $420/night

    Paki Maui 226

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $238 to $446/night

    Kahana Sunset D11

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $310 to $649/night

    Maui Kai 805 Ocean View 1 bedroom/1 bath

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $668 to $2,681/night

    Makena Surf B305

    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. $170 to $254/night

    Kihei Akahi D604

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $218 to $566/night

    Sugar Beach 502

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $136 to $237/night

    Maui Sunset B204

    1 BedroomBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $333 to $509/night

    Maalaea Kai #410

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $271 to $795/night

    Hololani B802

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $254 to $863/night

    Island Surf 614

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $299 to $1,021/night

    Kapalua Bay Villa 32G4

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $231 to $724/night

    Pacific Shores B118

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $520 to $2,054/night

    Wailea Elua 2303

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $659 to $2,017/night

    Noelani 307

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $249 to $524/night

    Haleakala Shores A403

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $283 to $1,101/night

    Grand Champions 138

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $987 to $4,517/night

    Ho'olei 39-3

    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. $396 to $1,728/night

    Wailea Ekahi 34B

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $287 to $1,131/night

    Menehune Shores 102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $166 to $563/night

    Kihei Kai Nani #8-362

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $208 to $544/night

    Hale Ono Loa 411

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $312 to $1,172/night

    Luana Kai D305

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $324 to $991/night

    Wailea Ekahi 47E

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $520 to $1,729/night

    Honua Kai Hokulani 310

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $604 to $2,918/night

    Makena Surf F201

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $249 to $738/night

    Maalaea Kai 215

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $343 to $1,280/night

    Luana Kai D301

    2 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. $1,038 to $5,010/night

    Ho'olei 17-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $3,035 to $12,174/night

    Wailea Beach Villa B102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $808 to $2,969/night

    Wailea Beach Villa J106

    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. $1,558 to $5,164/night

    The Cove Hale

    4 BedroomsBathroomsSleeps 16
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $289 to $998/night

    Palms at Wailea 609

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $274 to $1,192/night

    Wailea Ekolu 208

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $231 to $954/night

    Grand Champions 145

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $289 to $846/night

    Royal Kahana 1207

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $274 to $756/night

    Kapalua Golf Villas 21T1

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $213 to $333/night

    Kamaole Sands 8-101

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $1,038 to $3,879/night

    Wailea Beach Villa H202

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $458 to $1,609/night

    Royal Mauian 204

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $572 to $2,137/night

    Maui Hill 66

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $281 to $1,305/night

    Grand Champions 130

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $250 to $678/night

    Kamaole Sands 6-104

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $306 to $1,329/night

    Wailea Ekolu 904

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $576 to $1,374/night

    Mana Kai #203

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