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. $312 to $1,085/night

    Lauloa 407

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
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  3. $549 to $1,583/night

    Mana Kai #303

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
    FREE CANCELLATION
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  5. $520 to $1,883/night

    Mana Kai #614

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
    FREE CANCELLATION
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  7. $491 to $1,583/night

    Royal Mauian 512

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  8. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  9. $289 to $911/night

    Wailea Ekahi 26B

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
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  11. $214 to $763/night

    Kauhale Makai 203

    Multiple Units Available
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
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  13. $520 to $1,883/night

    Mana Kai #814

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
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  15. $404 to $1,100/night

    Maalaea Surf G8

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  16. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  17. $156 to $361/night

    Valley Isle Resort 507

    Studio BathroomSleeps 3
    3 nights minstay
    Pool
  18. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  19. $1,154 to $5,720/night

    Wailea Beach Villa M312

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  20. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  21. $375 to $1,011/night

    Kihei Surfside 506

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  22. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  23. $375 to $1,033/night

    Kihei Surfside 412

    1 Bedroom1.5  BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  24. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  25. $1,212 to $4,554/night

    Wailea Elua 1603

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  26. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  27. $300 to $868/night

    Sugar Beach Resort 328

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  28. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  29. $621 to $1,116/night

    Kahana Sunset A7

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool
  30. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  31. $936 to $1,411/night

    Sands Of Kahana 384

    1 BedroomBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  32. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  33. $208 to $783/night

    Napili Point B35

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  34. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  35. $577 to $1,644/night

    Mana Kai #403

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
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  37. $318 to $797/night

    Maalaea Banyans 217

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $357 to $1,341/night

    Wailea Ekahi 40D

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  40. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  41. $2,958 to $11,468/night

    Wailea Beach Villa B202

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  43. $289 to $849/night

    Milowai 101

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $433 to $1,603/night

    Wailea Ekahi 39E

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  46. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  47. $283 to $763/night

    Mahina Surf 111

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $923 to $2,740/night

    Polo Beach Club 106

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  50. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  51. $404 to $1,221/night

    Maui Sunset B217

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $215 to $877/night

    Kahana Village 40 Oceanfront 2Bed/2Bath

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
    FREE CANCELLATION
  54. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  55. $212 to $644/night

    Papakea L207 Ocean Front 1 Bedroom

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $2,532 to $10,440/night

    Andaz Villa 810

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $224 to $729/night

    Napili Shores A203 Ocean Front Studio

    Studio BathroomSleeps 2
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $151 to $344/night

    Kuleana 405 Oceanfront 1 Bedroom

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $249 to $681/night

    Kahana Reef 217

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $687 to $1,176/night

    Mana Kai #412

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $267 to $939/night

    Island Sands 600

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $362 to $1,257/night

    Menehune Shores 112

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $283 to $1,147/night

    Nohonani 102

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $304 to $1,051/night

    Maalaea Banyan 416

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $467 to $1,464/night

    My Waii Beach Cottage

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    FREE CANCELLATION
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $403 to $1,407/night

    Kamaole Nalu 504

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $374 to $766/night

    Honua Kai Hokulani 824

    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. $989 to $2,906/night

    Honua Kai Konea 250

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $260 to $1,107/night

    Wailea Ekahi 48E

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $254 to $752/night

    Sugar Beach Resort 209

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $318 to $1,340/night

    Wailea Ekahi 25B

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $318 to $1,130/night

    Wailea Ekahi 53D

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $577 to $2,098/night

    Wailea Ekahi 48A

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $458 to $1,608/night

    Royal Mauian 204

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $197 to $573/night

    Kuleana Resort 303

    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. $477 to $2,169/night

    Wailea Ekahi 26A

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $808 to $2,974/night

    Wailea Beach Villa J106

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $246 to $1,004/night

    Wailea Ekahi 36E

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $343 to $1,280/night

    Luana Kai D301

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $214 to $634/night

    Sugar Beach Resort PH8

    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. $604 to $2,924/night

    Makena Surf F201

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $485 to $1,700/night

    Mana Kai #805

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $520 to $1,689/night

    Honua Kai Hokulani 310

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $750 to $3,970/night

    Wailea Beach Villa I204

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $333 to $1,038/night

    Luana Kai C306

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $312 to $1,170/night

    Luana Kai D305

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $208 to $547/night

    Hale Ono Loa 411

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $318 to $914/night

    Wailea Ekahi 25A

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $767 to $2,974/night

    Wailea Beach Villa H102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $396 to $1,724/night

    Wailea Ekahi 34B

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $528 to $1,513/night

    Royal Mauian 206

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $1,096 to $5,113/night

    Wailea Beach Villa I503

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $261 to $632/night

    Maui Kai 607

    Studio BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $250 to $688/night

    Hale Kai 115

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $212 to $740/night

    Maui Sunset A504

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $323 to $1,103/night

    Palms at Wailea 601

    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. $701 to $3,474/night

    Wailea Elua 2305

    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. $272 to $808/night

    Sugar Beach Resort 409

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $340 to $1,105/night

    Island Sands 306

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $230 to $601/night

    Kahana Reef 305

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $554 to $1,824/night

    Mana Kai #705

    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. $467 to $1,449/night

    Mana Kai #815

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $289 to $970/night

    Wailea Ekahi 36B

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $353 to $1,387/night

    Kamaole Nalu 402

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $469 to $1,789/night

    Wailea Ekahi 5E

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $208 to $588/night

    Valley Isle 301

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $576 to $1,374/night

    Mana Kai #203

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $243 to $692/night

    Kahana Reef 120

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $668 to $2,681/night

    Makena Surf B305

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $243 to $766/night

    Maalaea Banyans 102

    Multiple Units Available
    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 $3,879/night

    Wailea Beach Villa H202

    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. $288 to $911/night

    Sugar Beach Resort 235

    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. $289 to $850/night

    Royal Kahana 1207

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $329 to $883/night

    Kapalua Bay Villas 37G1

    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. $3,035 to $11,631/night

    Wailea Beach Villa B102

    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. $312 to $1,044/night

    Kamaole Nalu 103

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $334 to $1,002/night

    Kaanapali Royal G303

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $301 to $1,248/night

    Maui Sunset B317

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $249 to $734/night

    Maalaea Kai 215

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $203 to $672/night

    Maalaea Banyans 104

    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. $279 to $1,018/night

    Kauhale Makai 433

    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. $300 to $1,243/night

    Wailea Ekahi 45A

    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. $404 to $1,571/night

    Mana Kai #508

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $324 to $993/night

    Wailea Ekahi 47E

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $278 to $954/night

    Waiohuli Beach Hale C211

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $249 to $918/night

    Maalaea Banyans 412

    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. $287 to $1,130/night

    Menehune Shores 102

    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