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. $263 to $421/night

    KIHEI BEACH, #110

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
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  3. $202 to $387/night

    SUGAR BEACH RESORT, #129

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
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  5. $212 to $309/night

    KIHEI BEACH, #203

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
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  7. $336 to $505/night

    ROYAL MAUIAN, #517

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
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  9. $223 to $321/night

    KEALIA RESORT, #304

    2 Bedrooms BathroomSleeps 4
    5 nights minstay
    Pool
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  11. $247 to $393/night

    MAALAEA SURF, #F-2

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
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  13. $263 to $421/night

    KIHEI BEACH, #402

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
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  15. $212 to $309/night

    KIHEI BEACH, #504

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
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  17. $309 to $556/night

    WAILEA GRAND CHAMPION, #180^

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
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  19. $335 to $454/night

    Pacific Shores B414

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  20. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  21. $463 to $610/night

    Hanalei Colony Resort I1

    2 Bedrooms1.5  BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
  22. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  23. $150 to $490/night

    Ilikai Tower 936

    Multiple Units Available
    1 night minstay
    Pool
    FREE CANCELLATION
  24. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  25. $202 to $448/night

    Poolside Aina Nalu Condo A101

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  26. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  27. $293 to $770/night

    Lahaina Shores Condo 701

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  28. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  29. $322 to $833/night

    Puamana Premier Plus Townhouse 161-2

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  30. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  31. $338 to $374/night

    Maalaea Banyans 203

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  32. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  33. $170/night

    Islander on the Beach 259

    Studio BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  34. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  35. $336 to $727/night

    Sea Village 1105

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
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  37. $259 to $508/night

    Kona Makai 4104

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
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  39. $381 to $863/night

    Mauna Lani Fairways #102

    3 Bedrooms2.5 BathroomsSleeps 8
    2 nights minstay
    Pool
  40. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  41. $423 to $954/night

    Pili Mai 6K

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  42. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  43. $304 to $481/night

    Valley Isle 902

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $750 to $2,058/night

    Pohaku Villa

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
  46. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  47. $226 to $257/night

    Alii Kai II 11B

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $173 to $381/night

    Noelani #219

    Studio BathroomSleeps 2
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  50. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  51. $146 to $183/night

    Perfect for Extended Stays! Two Pools & Two Hot Tubs...

    2 BedroomsBathroomsSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $214 to $238/night

    Puamana 21D

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool
    FREE CANCELLATION
  54. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  55. $294 to $436/night

    Kihei Alii Kai A207

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $314 to $941/night

    Aina Nalu D-207: Affordable luxury at it's best!

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $141 to $152/night

    Paniolo Hale C1

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $145 to $569/night

    Lahaina Shores 210

    Studio BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $129 to $158/night

    Kuhio Village Condominium 1005A *Legal Vacation Rental

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $314 to $563/night

    Ewa Hotel Waikiki #510

    Studio BathroomSleeps 3
    4 nights minstay
    FREE CANCELLATION
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $377 to $563/night

    Ewa Hotel Waikiki #307

    Studio BathroomSleeps 4
    4 nights minstay
    FREE CANCELLATION
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $304 to $568/night

    Beach Villas at Kahalu'u 2-101

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $423 to $883/night

    Pili Mai 7M

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $383 to $865/night

    Hale Alaula- Ocean View

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Hot Tub
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $925 to $1,434/night

    Hale Kauka

    3 Bedrooms2.5 BathroomsSleeps 7
    2 nights minstay
    Pool
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $417 to $931/night

    Paradise Bluff

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $506 to $899/night

    Holua Kai #34

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $690 to $1,279/night

    Hale Anu Keanu

    4 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Hot Tub
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $299 to $644/night

    Kona Plaza 201

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $375 to $776/night

    Banyan Tree 200

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $158 to $596/night

    Kuhio Village Condominium 701A *Legal Vacation Rental

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $194 to $279/night

    Sea Village 1-205-Oceanfront

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $183 to $584/night

    Aina Nalu C205

    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. $219 to $242/night

    Bamboo Waikiki #1204

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $240 to $876/night

    Fairway Villas M2 at the Waikoloa Beach Resort

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $199 to $369/night

    Kahana Villa 2BR w/ Ocean-View Lanai, Pool & Spa

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $310 to $605/night

    Melemele Pua

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $334 to $444/night

    Sugar Beach #120

    1 Bedroom BathroomSleeps 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. $261 to $326/night

    Maui Parkshore #105

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
    FREE CANCELLATION
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $283 to $600/night

    Papakea #K203

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $238 to $478/night

    Hale 'Olu'Olu

    3 Bedrooms2.5 BathroomsSleeps 8
    5 nights minstay
    Pool
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $340/night

    223

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pool
    FREE CANCELLATION
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $318 to $426/night

    Sugar Beach #618

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $238 to $478/night

    Tropical Breeze

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool Hot Tub
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $258/night

    111

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $340/night

    275

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $342 to $646/night

    Hale Kaimana

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $223 to $661/night

    Poolside Aina Nalu Condo D101

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $428 to $910/night

    Puamana Townhouse 64-1

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $308 to $430/night

    Aina Nalu I204

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $329/night

    Turtle Bay Kona Coffee***TA-163265126401 Available 30 ni...

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $218/night

    Turtle Bay North Shore Golf TA-151246848001 Available 30...

    2 Bedrooms2.5 BathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $180 to $619/night

    Kuhio Village Condominium 1201A *LEGAL VACATION RENTAL

    1 Bedroom1.5  BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $141 to $197/night

    Maui Vista #1218

    1 Bedroom BathroomSleeps 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. $129 to $158/night

    Waikiki Grand Condominium 705 *Legal Vacation Rental

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $312 to $689/night

    Maui Eldorado Condo J123

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $85 to $151/night

    Discovery Bay 2907

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $202/night

    Turtle Bay Heliconia**TA-207435366401 Available 30 days

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $133 to $186/night

    Discovery Bay 3619

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $221 to $308/night

    Shores at Waikoloa #234 at Bo Tree Tower

    2 BedroomsBathroomsSleeps 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. $173 to $375/night

    Valley Isle #1104

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $330 to $689/night

    Big Island Paradise

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $219 to $242/night

    Bamboo Waikiki #1003

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $601 to $1,501/night

    Plantation Cottage at Poipu

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $232 to $464/night

    Kona Mansions Breeze

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $482 to $780/night

    Keauhou Estates #185

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Hot Tub
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $506 to $899/night

    Holua Kai #32

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $393 to $688/night

    Nohea Villa

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $499 to $729/night

    Kaanapali Royal Q101

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $207/night

    Turtle Bay Kekoa*TA-185993420801 Available 30 nights

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $161/night

    Turtle Bay Hale Kuilima**TA-114877030401 Available 30 ni...

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $340/night

    328

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $1,679/night

    Hale Lani

    4 BedroomsBathroomsSleeps 14
    3 nights minstay
    Pool
    FREE CANCELLATION
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $234 to $308/night

    Waikoloa Beach Villas E32

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $501 to $557/night

    Sands Of Kahana 275

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $258/night

    173

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $519 to $719/night

    Kaanapali Shores 527

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $415 to $824/night

    2BR Beachfront Condo w/ Ocean View

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $1,018 to $1,880/night

    Mauna Kea Villas #13

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $340/night

    245

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $412 to $533/night

    Waikoloa Beach Villas I1

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $261 to $326/night

    Maui Parkshore #114

    2 BedroomsBathroomsSleeps 5
    7 nights minstay
    Pool
    FREE CANCELLATION
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $341 to $413/night

    1 Bedroom Oceanfront #604

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $169 to $471/night

    New Listing! “Kona Sunset Hale” w/ Ocean Views

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    FREE CANCELLATION
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $258/night

    123

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $219 to $242/night

    Bamboo Waikiki #1103

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $296 to $356/night

    Maui Banyan #H-308

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  200. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations