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. $209 to $532/night

    Hololani #B-802

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
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  3. $138 to $307/night

    Valley Isle #107

    Studio BathroomSleeps 3
    3 nights minstay
    Pool
    FREE CANCELLATION
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  5. $335 to $1,133/night

    Royal Kahana #911

    2 Bedrooms2.5 BathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
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  7. $126 to $400/night

    Royal Kahana #319

    Studio BathroomSleeps 3
    3 nights minstay
    Pool
    FREE CANCELLATION
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  9. $269 to $609/night

    Kaanapali Royal #H302

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
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  11. $269 to $563/night

    Kaanapali Royal #C101

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
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  13. $406 to $706/night

    Kaanapali Shores #916

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
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  15. $319 to $706/night

    Kaanapali Shores #825

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
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  17. $247 to $539/night

    Pikake #A6

    2 Bedrooms1.5  BathroomSleeps 6
    3 nights minstay
    FREE CANCELLATION
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  19. $275 to $615/night

    Papakea #L407

    2 Bedrooms BathroomSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
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  21. $297 to $606/night

    Mahana Resort #1017

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
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  23. $319 to $606/night

    Mahana Resort #304

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
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  25. $303 to $574/night

    Mahana Resort #804

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
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  27. $307 to $669/night

    Mahana Resort #706

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  28. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  29. $181 to $331/night

    Maui Kaanapali Villas #C152

    Studio BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  30. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  31. $220 to $406/night

    Maui Kaanapali Villas #B133

    Studio BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  32. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  33. $203 to $331/night

    Maui Kaanapali Villas #B242

    Studio BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
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  35. $281 to $447/night

    Maui Kaanapali Villas #B233

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  36. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  37. $275 to $586/night

    Papakea #G408

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $331 to $669/night

    Lahaina Shores #501

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  40. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  41. $264 to $640/night

    Lokelani #C205

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  42. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  43. $176 to $452/night

    Papakea #A105

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $154 to $332/night

    Paki Maui #109

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  46. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  47. $495 to $899/night

    Papakea #C403

    3 BedroomsBathroomsSleeps 7
    3 nights minstay
    Pool
    FREE CANCELLATION
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $137 to $302/night

    Papakea #B207

    Studio BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  50. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  51. $193 to $365/night

    Papakea #C108

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
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  53. $275 to $505/night

    Papakea #G106

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool
    FREE CANCELLATION
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  55. $154 to $342/night

    Papakea #D309

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $171 to $418/night

    Papakea #D304

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $247 to $619/night

    Papakea #E401

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool
    FREE CANCELLATION
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $203 to $719/night

    Valley Isle #1103

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $247 to $615/night

    Lahaina Shores #425

    Studio BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $121 to $249/night

    Paki Maui #420

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $264 to $603/night

    Kaanapali Royal #A303

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $215 to $464/night

    Maui Kaanapali Villas #C255

    Studio BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $309 to $638/night

    Mahana Resort #1106

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $253 to $580/night

    Papakea #H103

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $385 to $566/night

    Paki Maui #421

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $181 to $408/night

    Lokelani #C104

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $198 to $414/night

    Lahaina Roads #206

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $253 to $684/night

    Lahaina Roads #201

    2 Bedrooms BathroomSleeps 5
    3 nights minstay
    Pool
    FREE CANCELLATION
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $259 to $696/night

    Lahaina Shores #531

    Studio BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $209 to $532/night

    Hololani #B-403

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $293 to $574/night

    Kaanapali Royal #N302

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $354 to $719/night

    Mahana Resort #616

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $325 to $557/night

    Papakea #A109

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $113 to $135/night

    Kepuhi Beach 1192

    Studio BathroomSleeps 3
    3 nights minstay
    Pool
    FREE CANCELLATION
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $305 to $371/night

    Kihei Akahi #DG-02

    2 BedroomsBathroomsSleeps 4
    7 nights minstay
    Pool
    FREE CANCELLATION
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $468 to $594/night

    Kapalua Golf Villas #12T5

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $398 to $480/night

    Kamaole Sands #10-404

    2 BedroomsBathroomsSleeps 5
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $296 to $332/night

    Kamaole Sands #01-302

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $267 to $326/night

    Kauhale Makai #222

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $267 to $326/night

    Kauhale Makai #331

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $305 to $390/night

    Kauhale Makai #433

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $267 to $326/night

    Kauhale Makai #627

    1 Bedroom BathroomSleeps 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. $344 to $460/night

    Kihei Surfside #107

    1 Bedroom BathroomSleeps 4
    7 nights minstay
    Pool
    FREE CANCELLATION
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $344 to $460/night

    Kihei Surfside #613

    1 Bedroom1.5  BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $428 to $546/night

    Maui Kamaole #C-209

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $297 to $390/night

    Maui Kamaole #D-104

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $428 to $546/night

    Maui Kamaole #J-214

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $297 to $390/night

    Maui Kamaole #M-104

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $563/night

    Kahana Reef #322

    Studio BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $304 to $350/night

    Maui Vista #1406

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $304 to $350/night

    Maui Vista #1407

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $304 to $350/night

    Maui Vista #3420

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $379 to $539/night

    Whaler at Kaanapali Beach #163

    Studio BathroomSleeps 2
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $528 to $774/night

    Whaler at Kaanapali Beach #912

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $294 to $563/night

    Kapalua Bay Villa 15G5 Ocean View

    1 BedroomBathroomsSleeps 4
    4 nights minstay
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $750 to $1,406/night

    Kapalua Bay Villa 32B2 Gold Ocean View

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $581 to $1,106/night

    Kapalua Bay Villa 23B3 Ocean Front

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $594 to $869/night

    Kapalua Bay Villa 30B1 Gold Ocean Front

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $494 to $1,031/night

    Kapalua Ridge Villa 1112 Gold Ocean View

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $344 to $619/night

    Kapalua Bay Villa 17B4 Gold Ocean View

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $306 to $563/night

    Kapalua Ridge Villa 1511 Gold Ocean View

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $438 to $906/night

    Kapalua Bay Villa 11B3-4 Gold Ocean View

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $525 to $1,031/night

    Kapalua Ridge Villa 2614 Gold Ocean View

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $249 to $327/night

    Papakea A307

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $256 to $661/night

    Maui Eldorado Condo A104

    1 Bedroom BathroomSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $219 to $242/night

    Bamboo Waikiki #1004

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $278 to $422/night

    Bamboo Waikiki #903

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $393 to $874/night

    Hale Luana (Big Island)

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
    Hot Tub
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $390 to $488/night

    Maui Banyan #G-201

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $224 to $499/night

    Maui Eldorado Condo K218

    Studio BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $244 to $563/night

    Ewa Hotel Waikiki #503

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    FREE CANCELLATION
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $314 to $563/night

    Ewa Hotel Waikiki #507

    Studio BathroomSleeps 3
    4 nights minstay
    FREE CANCELLATION
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $199 to $589/night

    Luxe 3BR w/ Pool & 2 Private Lanais, Walk to Beach

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $305 to $390/night

    Kauhale Makai #212

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $115 to $560/night

    Oceanfront Nohonani- Unforgettable Views

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
    FREE CANCELLATION
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $189 to $588/night

    3BR Pacific Paradise w/ Pool- 5 Minutes to Beach

    3 Bedrooms2.5 BathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $259 to $623/night

    New Listing! 2-Acre Retreat w/ Pool, Ocean Views

    4 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pool
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $134 to $252/night

    Oceanfront Condo w/ Resort Amenities

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $423 to $810/night

    Pili Mai 3G

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $595 to $1,280/night

    Hale Kanani (Kaua'i) TVNC 1342

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $346 to $822/night

    Hale Oliveira

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $815 to $1,858/night

    Hale Pulelehua TVNC#1238

    4 Bedrooms2.5 BathroomsSleeps 8
    2 nights minstay
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $393 to $643/night

    Nohea Villa

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $1,434 to $3,267/night

    Blue Oasis

    5 BedroomsBathroomsSleeps 14
    2 nights minstay
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $167 to $404/night

    KIHEI SURFSIDE, #506

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $1,688 to $2,250/night

    Hale Lahaina

    4 Bedrooms5.5 BathroomsSleeps 10
    5 nights minstay
    Pool
    FREE CANCELLATION
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $781 to $1,438/night

    Kapalua Bay Villa 20G2 Gold Beach Front

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