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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. $1,434 to $3,267/night

    Blue Oasis

    5 Bedrooms, 5 Bathrooms, Sleeps 14
    2 nights minstay
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  3. $280 to $426/night

    Great Summer Price! Close to the Beaches & Shopping!...

    3 Bedrooms, 2 Bathrooms, Sleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  5. $107 to $208/night

    Kuhio Village 410 Condominium

    1 Bedroom, 1  Bathroom, Sleeps 2
    2 nights minstay
    FREE CANCELLATION
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  7. $321 to $523/night

    Diamond Head Beach Hotel 801

    1 Bedroom, 1  Bathroom, Sleeps 2
    2 nights minstay
    FREE CANCELLATION
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  9. $190 to $623/night

    Coconut Condos- Aina Nalu Premier Condo B108

    2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
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  11. $202 to $636/night

    Coconut Condos- Aina Nalu Condo J209

    2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
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  13. $202 to $636/night

    Coconut Condos- Aina Nalu Condo B103

    2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
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  15. $393 to $643/night

    Nohea Villa

    3 Bedrooms, 3 Bathrooms, Sleeps 6
    2 nights minstay
    Pool Hot Tub
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  17. $167 to $303/night

    Pacific Monarch 3101 Condo

    1 Bedroom, 1  Bathroom, Sleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
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  19. $144 to $280/night

    Bamboo 709 Condo

    Studio, 1  Bathroom, Sleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
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  21. $968 to $1,688/night

    Diamond Head Beach Hotel Rooftop 1402

    3 Bedrooms, 2 Bathrooms, Sleeps 6
    2 nights minstay
    FREE CANCELLATION
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  23. $360 to $501/night

    Diamond Head Beach Hotel 701

    2 Bedrooms, 1  Bathroom, Sleeps 4
    2 nights minstay
    FREE CANCELLATION
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  25. $167 to $253/night

    Palms Waikiki 220 Studio

    Studio, 1  Bathroom, Sleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
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  27. $180 to $609/night

    Coconut Condos- Aina Nalu Premier Condo H110

    2 Bedrooms, 1  Bathroom, Sleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
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  29. $144 to $280/night

    Bamboo 610 Studio Apartment

    Studio, 1  Bathroom, Sleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  31. $202 to $2,496/night

    Coconut Condos- Aina Nalu Premier Platinum Condo D203

    2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
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  33. $144 to $280/night

    Bamboo 505 Condominium

    Studio, 1  Bathroom, Sleeps 4
    2 nights minstay
    FREE CANCELLATION
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  35. $219 to $349/night

    Diamond Head Beach Hotel 802

    1 Bedroom, 1  Bathroom, Sleeps 2
    2 nights minstay
    FREE CANCELLATION
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  37. $219 to $349/night

    Diamond Head Beach Hotel 1202

    1 Bedroom, 1  Bathroom, Sleeps 3
    2 nights minstay
    FREE CANCELLATION
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  39. $393 to $874/night

    Hale Luana (Big Island)

    4 Bedrooms, 3 Bathrooms, Sleeps 10
    2 nights minstay
    Hot Tub
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  41. $144 to $280/night

    Bamboo 308 Condominium

    Studio, 1  Bathroom, Sleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  43. $107 to $208/night

    Kuhio Village 1103 Condominium

    Studio, 1  Bathroom, Sleeps 3
    2 nights minstay
    FREE CANCELLATION
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  45. $142 to $290/night

    Waikiki Grand 412 Condo

    Studio, 1  Bathroom, Sleeps 3
    2 nights minstay
    FREE CANCELLATION
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  47. $142 to $290/night

    Waikiki Grand 805 Condo

    1 Bedroom, 1  Bathroom, Sleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
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  49. $142 to $290/night

    Waikiki Grand 715 Condo

    1 Bedroom, 1  Bathroom, Sleeps 2
    2 nights minstay
    Pool Pets OK
    FREE CANCELLATION
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  51. $190 to $623/night

    Coconut Condos- Aina Nalu Premier Condo G108

    2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
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  53. $115 to $219/night

    Aloha Surf 315 Hotel Suites

    1 Bedroom, 1  Bathroom, Sleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
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  55. $107 to $208/night

    Waikiki Grand 701 Studio

    1 Bedroom, 1  Bathroom, Sleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
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  57. $107 to $208/night

    Waikiki Grand 500 Condo

    Studio, 1  Bathroom, Sleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
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  59. $167 to $253/night

    Tradewinds Plaza 305

    1 Bedroom, 1  Bathroom, Sleeps 3
    2 nights minstay
    FREE CANCELLATION
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  61. $257 to $741/night

    Coconut Condos- Pohailani 231

    2 Bedrooms, 1  Bathroom, Sleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
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  63. $142 to $290/night

    Diamond Head Beach Hotel 1105

    1 Bedroom, 1  Bathroom, Sleeps 2
    2 nights minstay
    FREE CANCELLATION
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  65. $225 to $281/night

    A Ala Hale

    2 Bedrooms, 2 Bathrooms, Sleeps 4
    3 nights minstay
    FREE CANCELLATION
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  67. $167 to $253/night

    Banyan 1608-I Condominium

    1 Bedroom, 1  Bathroom, Sleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  69. $141 to $169/night

    Paniolo Hale R2

    1 Bedroom, 2 Bathrooms, Sleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
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  71. $142 to $290/night

    Diamond Head Beach Hotel 1005

    1 Bedroom, 1  Bathroom, Sleeps 4
    2 nights minstay
    FREE CANCELLATION
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  73. $142 to $290/night

    Waikiki Grand 719

    Studio, 1  Bathroom, Sleeps 2
    2 nights minstay
    Pool Pets OK
    FREE CANCELLATION
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  75. $144 to $280/night

    Bamboo 902 Hotel Suites

    1 Bedroom, 1  Bathroom, Sleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  77. $202 to $636/night

    Coconut Condos- Aina Nalu Condo K107

    2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  79. $202 to $636/night

    Coconut Condos- Aina Nalu Condo A209

    2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  81. $202 to $636/night

    Coconut Condos- Aina Nalu Condo C208

    2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  83. $169 to $225/night

    Ke Nani Kai 218

    2 Bedrooms, 2 Bathrooms, Sleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  85. $152 to $197/night

    Ke Nani Kai 237

    2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  87. $225 to $338/night

    Hale Hiamoe

    3 Bedrooms, 2 Bathrooms, Sleeps 6
    3 nights minstay
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  89. $202 to $636/night

    Coconut Condos- Aina Nalu C108

    2 Bedrooms, 2 Bathrooms, Sleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  91. $202 to $636/night

    Coconut Condos- Aina Nalu Condo K202

    2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  93. $115 to $219/night

    Aloha Surf 1507 Condominium

    1 Bedroom, 1  Bathroom, Sleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  95. $113 to $135/night

    Kepuhi Beach 1234

    Studio, 1  Bathroom, Sleeps 2
    3 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 Bedroom, 2 Bathrooms, Sleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  99. $297 to $396/night

    Sugar Beach #302

    1 Bedroom, 1  Bathroom, Sleeps 4
    4 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 $279/night

    Maui Vista #1302

    1 Bedroom, 1  Bathroom, Sleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  103. $344 to $460/night

    Kihei Surfside #212

    1 Bedroom, 1.5  Bathroom, Sleeps 2
    4 nights minstay
    Pool
    FREE CANCELLATION
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  105. $297 to $390/night

    Maui Kamaole #M-104

    1 Bedroom, 2 Bathrooms, Sleeps 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. $384 to $488/night

    Maui Kamaole #D-211

    2 Bedrooms, 2 Bathrooms, Sleeps 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. $428 to $546/night

    Maui Kamaole #H-201

    2 Bedrooms, 2 Bathrooms, Sleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  111. $325 to $417/night

    Grand Champions #054

    1 Bedroom, 2 Bathrooms, Sleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  113. $390 to $488/night

    Maui Banyan #F-206

    2 Bedrooms, 2 Bathrooms, Sleeps 6
    7 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  115. $246 to $279/night

    Maui Vista #3301

    1 Bedroom, 1  Bathroom, Sleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  117. $304 to $350/night

    Maui Vista #1407

    2 Bedrooms, 2 Bathrooms, Sleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  119. $246 to $279/night

    Maui Vista #1306

    1 Bedroom, 1  Bathroom, Sleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  121. $246 to $279/night

    Maui Vista #1323

    1 Bedroom, 1  Bathroom, Sleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  123. $334 to $444/night

    Sugar Beach #425

    1 Bedroom, 1  Bathroom, Sleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  125. $188 to $443/night

    Kaleialoha #305

    1 Bedroom, 1  Bathroom, Sleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  127. $269 to $363/night

    276

    2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  129. $779 to $1,188/night

    Whaler at Kaanapali Beach #1173

    2 Bedrooms, 2 Bathrooms, Sleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  131. $337/night

    Kona Isle D4

    1 Bedroom, 1  Bathroom, Sleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  133. $118 to $208/night

    Hawaiian King 112 Condo

    1 Bedroom, 1  Bathroom, Sleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  135. $223 to $410/night

    Waikoloa Beach Villas O-33

    2 Bedrooms, 2 Bathrooms, Sleeps 5
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  137. $113 to $135/night

    Kepuhi Beach 1192

    Studio, 1  Bathroom, Sleeps 3
    3 nights minstay
    Pool
    FREE CANCELLATION
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  139. $398 to $480/night

    Kamaole Sands #10-404

    2 Bedrooms, 2 Bathrooms, Sleeps 5
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  141. $341 to $434/night

    Maui Kamaole #H-104

    1 Bedroom, 2 Bathrooms, Sleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  143. $305 to $371/night

    Kihei Akahi #DG-02

    2 Bedrooms, 2 Bathrooms, Sleeps 4
    7 nights minstay
    Pool
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  145. $305 to $390/night

    Kauhale Makai #433

    2 Bedrooms, 2 Bathrooms, Sleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  147. $246 to $279/night

    Maui Vista #1120

    1 Bedroom, 1  Bathroom, Sleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  149. $344 to $460/night

    Kihei Surfside #107

    1 Bedroom, 1  Bathroom, Sleeps 4
    7 nights minstay
    Pool
    FREE CANCELLATION
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  151. $253 to $311/night

    Leinaala #401

    1 Bedroom, 1  Bathroom, Sleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  153. $267 to $326/night

    Kauhale Makai #410

    1 Bedroom, 1  Bathroom, Sleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  155. $398 to $480/night

    Kamaole Sands #10-405

    2 Bedrooms, 2 Bathrooms, Sleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  157. $296 to $332/night

    Kamaole Sands #06-106

    1 Bedroom, 2 Bathrooms, Sleeps 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. $334 to $444/night

    Sugar Beach #334

    1 Bedroom, 1  Bathroom, Sleeps 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. $235 to $296/night

    Kihei Akahi #D-414

    1 Bedroom, 1  Bathroom, Sleeps 2
    4 nights minstay
    Pool
    FREE CANCELLATION
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  163. $428 to $543/night

    Grand Champions #118

    2 Bedrooms, 2 Bathrooms, Sleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  165. $428 to $546/night

    Maui Kamaole #C-207

    2 Bedrooms, 2 Bathrooms, Sleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  167. $528 to $774/night

    Whaler at Kaanapali Beach #912

    1 Bedroom, 2 Bathrooms, Sleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  169. $379 to $539/night

    Whaler at Kaanapali Beach #163

    Studio, 1  Bathroom, Sleeps 2
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  171. $231 to $267/night

    Kihei Bay Vista #C-202

    1 Bedroom, 1  Bathroom, Sleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  173. $390 to $488/night

    Maui Banyan #G-201

    2 Bedrooms, 2 Bathrooms, Sleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  175. $246 to $279/night

    Maui Vista #3111

    1 Bedroom, 1  Bathroom, Sleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  177. $581 to $1,106/night

    Kapalua Bay Villa 23B3 Ocean Front

    2 Bedrooms, 3 Bathrooms, Sleeps 6
    4 nights minstay
    Pool
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  179. $113 to $135/night

    Kepuhi Beach 1226

    Studio, 1  Bathroom, Sleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  181. $174 to $363/night

    Ilikai 1504

    1 Bedroom, 1  Bathroom, Sleeps 5
    2 nights minstay
    FREE CANCELLATION
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  183. $202 to $363/night

    Ilikai 1636

    1 Bedroom, 1  Bathroom, Sleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  185. $394 to $877/night

    Ilikai 1243

    2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  187. $504 to $811/night

    Pair of 2BR Hawaiian Cottages

    4 Bedrooms, 2 Bathrooms, Sleeps 8
    7 nights minstay
    FREE CANCELLATION
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  189. $218 to $502/night

    Kaleialoha #114

    1 Bedroom, 1  Bathroom, Sleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations

  191. $150 to $216/night

    Kihei Akahi D604

    1 Bedroom, 1  Bathroom, Sleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
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  193. $234 to $476/night

    Waikoloa Beach Villas H32

    2 Bedrooms, 2 Bathrooms, Sleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  195. $296 to $332/night

    Kamaole Sands #01-302

    1 Bedroom, 2 Bathrooms, Sleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  197. $305 to $390/night

    Kauhale Makai #512

    2 Bedrooms, 2 Bathrooms, Sleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  199. $356 to $417/night

    Kamaole Sands #04-406

    2 Bedrooms, 2 Bathrooms, Sleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  200. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
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