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. $277 to $373/night

    Fairway Villas Waikoloa O21

    2 BedroomsBathroomsSleeps 5
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  3. $277 to $416/night

    Waikoloa Beach Villas P32

    2 BedroomsBathroomsSleeps 5
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  5. $288 to $406/night

    Waikoloa Beach Villas C3

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  7. $555 to $801/night

    Ainamalu at Waikoloa Beach Resort

    3 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    FREE CANCELLATION
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  9. $416 to $716/night

    Fairway Villas Waikoloa F6

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  11. $331 to $491/night

    Colony Villas at Waikoloa Beach Resort #301

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  13. $331 to $534/night

    Colony Villas at Waikoloa Beach Resort #204

    2 Bedrooms2.5 BathroomsSleeps 5
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  15. $270 to $499/night

    Kahana Sunset B7

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool
  16. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  17. $209 to $525/night

    Kona Pacific B409

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
  18. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  19. $565 to $1,193/night

    Laulea Hale

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
    FREE CANCELLATION
  20. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  21. $167 to $561/night

    Banyan Harbor K132 at Kalapaki Beach

    2 Bedrooms1.5  BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  22. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  23. $365 to $730/night

    Napili Point C12 2 Bedroom Condo

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
    FREE CANCELLATION
  24. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  25. $184 to $323/night

    Kuleana 622 1 Bedroom Condo

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  26. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  27. $430 to $897/night

    Sands of Kahana 282 2 Bedroom Condo

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  28. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  29. $325 to $686/night

    Napili Shores A106 Studio Condo

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  30. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  31. $222 to $493/night

    Kaleialoha 106 1 Bedroom Condo

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  32. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  33. $644 to $2,018/night

    Sands Of Kahana PH 381 3Bd/3Ba OF

    3 BedroomsBathroomsSleeps 10
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  34. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  35. $512 to $1,017/night

    Honua Kai 215 2 Bed/2 Bath

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  36. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  37. $205 to $493/night

    Napili Point B33 1 Bedroom Oceanfront Condo

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $325 to $686/night

    Napili Shores A202 OF Studio

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  40. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  41. $111 to $656/night

    Sealodge H9

    1 Bedroom BathroomSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  42. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  43. $126 to $368/night

    Casa De Emdeko 332

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $148 to $352/night

    Valley Isle #905

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  46. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  47. $394 to $735/night

    Hale Mahina #B403

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $291 to $516/night

    Royal Kahana #209

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  50. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  51. $473 to $590/night

    Kaanapali Shores #159

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $629 to $972/night

    Kaanapali Shores #255

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  54. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  55. $532 to $840/night

    The Mahana #1204

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $247 to $502/night

    The Mahana #518

    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. $302 to $603/night

    The Mahana #906

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $415 to $893/night

    Maui Kaanapali Villas #A317

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $198 to $532/night

    Maui Kaanapali Villas #E290

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $415 to $515/night

    Maui Kaanapali Villas #A517

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $210 to $453/night

    Maui Sands #5G

    2 Bedrooms1.5  BathroomSleeps 5
    2 nights minstay
    FREE CANCELLATION
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $193 to $417/night

    Kahana Reef #116

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $209 to $402/night

    Kahana Reef #301

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $236 to $314/night

    Kahana Reef #211

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $185 to $365/night

    Kahana Reef #414

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $341 to $586/night

    Papakea #E207

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $373 to $641/night

    Papakea #G103

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $231 to $405/night

    Pohailani #102

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $219 to $612/night

    Kaanapali Plantation #52

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    FREE CANCELLATION
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $273 to $511/night

    Kahana Reef #310

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $446 to $893/night

    Maui Kaanapali Villas #A512

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $394 to $720/night

    Papakea #F407

    2 Bedrooms BathroomSleeps 6
    2 nights minstay
    FREE CANCELLATION
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $210 to $392/night

    Maui Sands #6E

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    FREE CANCELLATION
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $315 to $586/night

    Paki Maui #103

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Hot Tub
    FREE CANCELLATION
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $233 to $499/night

    Mahana At Kaanapali 306

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $231 to $447/night

    Pohailani #201

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $263 to $622/night

    Maui Kaanapali Villas #B247

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $135 to $525/night

    Kona Mansions#301

    1 Bedroom BathroomSleeps 3
    3 nights minstay
    Pool
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $184 to $420/night

    Keauhou Kona Surf & Racquet Club#10

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $252 to $473/night

    Kahana Sunset B3

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $935 to $1,705/night

    Big Island Private Home Alii Drive 6596

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $185 to $433/night

    Kaleialoha 209 1 Bedroom Condo

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $1,126 to $4,221/night

    Big Island Hualalai 133C

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $161 to $373/night

    Kaanapali Shores 642 Studio Condo

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $1,604 to $2,164/night

    Moloa'a Bay Villa & Cottage

    5 BedroomsBathroomsSleeps 11
    3 nights minstay
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $261 to $630/night

    Maui Kai 908 Oceanfront 1 Bedroom

    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. $254 to $752/night

    Sugar Beach Resort 209

    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. $312 to $1,044/night

    Kamaole Nalu 103

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $145 to $501/night

    Mauna Loa Shores #405

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $318 to $1,335/night

    Wailea Ekahi 25B

    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. $635 to $756/night

    Waipouli Beach Resort G-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $751 to $808/night

    Molokama Vacation Home in Hanalei Bay Near Beach

    4 BedroomsBathroomsSleeps 8
    3 nights minstay
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $143 to $404/night

    Kahana Sunset B3B

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $238 to $446/night

    Kahana Sunset D10

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $233 to $499/night

    Kahana Sunset D8

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $222 to $446/night

    Sands Of Kahana 231

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $233 to $499/night

    Kahana Sunset D2

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $528 to $1,129/night

    Sands Of Kahana 474

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $205 to $415/night

    Ridge Villa 1422

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $182 to $430/night

    Ali'i Kai 2201

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $230 to $420/night

    Paki Maui 226

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $238 to $446/night

    Kahana Sunset D11

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $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
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $320 to $493/night

    Pali Ke Kua #241

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $278 to $336/night

    Plantations at Princeville #111

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $210 to $525/night

    Keauhou Kona Surf & Racquet Club #5-202

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $668 to $2,681/night

    Makena Surf B305

    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. $203 to $249/night

    Hale Anuenue Nuku- The Rainbows End

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $118 to $279/night

    Peace of Paradise

    1 Bedroom1.25  BathroomSleeps 2
    3 nights minstay
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $170 to $254/night

    Kihei Akahi D604

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $735 to $1,426/night

    Hale Lani

    1 Bedroom BathroomSleeps 2
    2 nights minstay
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $220 to $237/night

    Hale O Makani

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $141 to $461/night

    Hale Ohi'a Lehua

    3 BedroomsBathroomsSleeps 8
    1 night minstay
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $81 to $467/night

    Maluhia Kahakai

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
    Pool
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $250 to $860/night

    Turtle Bay Kuilima Collection #101 East

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $136 to $237/night

    Maui Sunset B204

    1 BedroomBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $156 to $363/night

    Hale O Nani Mala Pua

    3 Bedrooms2.75 BathroomsSleeps 6
    3 nights minstay
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $257 to $473/night

    Keauhou Kona Surf & Racquet Club #1-103

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $263 to $525/night

    Keauhou Kona Surf & Racquet Club #8-301

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $331 to $415/night

    Pali Ke Kua #103

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool Hot Tub
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $125 to $488/night

    Kamahana 3 Spacious Private Condo with Yard

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool
    FREE CANCELLATION
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $394 to $735/night

    Halekii Sunset

    4 BedroomsBathroomsSleeps 11
    3 nights minstay
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $167 to $420/night

    Kona Magic Sands#213

    Studio BathroomSleeps 2
    3 nights minstay
    Pool
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $131 to $370/night

    Liko Lehua Cottage

    2 Bedrooms BathroomSleeps 4
    2 nights minstay
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $299 to $1,021/night

    Kapalua Bay Villa 32G4

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $140 to $550/night

    Hilo Hale Kaumana

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $184 to $420/night

    Kona Magic Sands#309

    Studio BathroomSleeps 2
    3 nights minstay
    Pool
  200. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations