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. $565 to $1,193/night

    Laulea Hale

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
    FREE CANCELLATION
  18. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  19. $167 to $561/night

    Banyan Harbor K132 at Kalapaki Beach

    2 Bedrooms1.5  BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  20. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  21. $111 to $656/night

    Sealodge H9

    1 Bedroom BathroomSleeps 5
    2 nights minstay
    Pool
    FREE CANCELLATION
  22. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  23. $142 to $293/night

    Kona Makai 3-302

    2 Bedrooms BathroomSleeps 6
    3 nights minstay
    Pool Hot Tub
  24. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  25. $209 to $402/night

    Kahana Reef #301

    1 Bedroom BathroomSleeps 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. $210 to $392/night

    Maui Sands #6E

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    FREE CANCELLATION
  28. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  29. $339 to $622/night

    Nihilani 32C

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  30. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  31. $233 to $499/night

    Mahana At Kaanapali 306

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
  32. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  33. $252 to $473/night

    Kahana Sunset B3

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool
  34. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  35. $1,126 to $4,221/night

    Big Island Hualalai 133C

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  36. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  37. $161 to $373/night

    Kaanapali Shores 642 Studio Condo

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $264 to $468/night

    KIHEI BEACH, #305*

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  40. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  41. $205 to $368/night

    Keauhou Kona Surf and Racquet Club Townhouse#185

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
  42. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  43. $904 to $1,243/night

    Haena Kai

    3 BedroomsBathroomsSleeps 7
    3 nights minstay
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $254 to $752/night

    Sugar Beach Resort 209

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  46. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  47. $145 to $501/night

    Mauna Loa Shores #405

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $318 to $1,335/night

    Wailea Ekahi 25B

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  50. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  51. $274 to $395/night

    Kona Oceanfront Condo w epic sunsets from private lanai

    2 Bedrooms1.5  BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $143 to $404/night

    Kahana Sunset B3B

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
  54. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  55. $238 to $446/night

    Kahana Sunset D10

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $233 to $499/night

    Kahana Sunset D8

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $222 to $446/night

    Sands Of Kahana 231

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $233 to $499/night

    Kahana Sunset D2

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $528 to $1,129/night

    Sands Of Kahana 474

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $205 to $415/night

    Ridge Villa 1422

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $216 to $331/night

    Valley Isle Resort 310

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $182 to $430/night

    Ali'i Kai 2201

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $238 to $446/night

    Kahana Sunset D11

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $210 to $525/night

    Keauhou Kona Surf & Racquet Club #5-202

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $420 to $735/night

    Hale Pahukoa

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pool
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $198 to $709/night

    White Sands Village#231

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $668 to $2,681/night

    Makena Surf B305

    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. $203 to $249/night

    Hale Anuenue Nuku- The Rainbows End

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $565 to $678/night

    Helen's Beach House

    5 BedroomsBathroomsSleeps 12
    7 nights minstay
    Pool
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $118 to $279/night

    Peace of Paradise

    1 Bedroom1.25  BathroomSleeps 2
    3 nights minstay
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $283 to $446/night

    Waikoloa Beach Villas O-33

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $735 to $1,426/night

    Hale Lani

    1 Bedroom BathroomSleeps 2
    2 nights minstay
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $220 to $237/night

    Hale O Makani

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $141 to $461/night

    Hale Ohi'a Lehua

    3 BedroomsBathroomsSleeps 8
    1 night minstay
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $277 to $469/night

    Emmalani Court 312

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $678 to $754/night

    Kailua Beachside

    4 BedroomsBathroomsSleeps 14
    7 nights minstay
    Pool
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $81 to $467/night

    Maluhia Kahakai

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
    Pool
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $480 to $1,727/night

    Poipu Shores 301B

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $1,175 to $3,331/night

    Hale Naninoa

    5 BedroomsBathroomsSleeps 11
    3 nights minstay
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $156 to $363/night

    Hale O Nani Mala Pua

    3 Bedrooms2.75 BathroomsSleeps 6
    3 nights minstay
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $257 to $473/night

    Keauhou Kona Surf & Racquet Club #1-103

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $125 to $488/night

    Kamahana 3 Spacious Private Condo with Yard

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool
    FREE CANCELLATION
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $448 to $1,957/night

    Waikiki Beach Tower 1104

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $394 to $735/night

    Halekii Sunset

    4 BedroomsBathroomsSleeps 11
    3 nights minstay
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $131 to $370/night

    Liko Lehua Cottage

    2 Bedrooms BathroomSleeps 4
    2 nights minstay
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $305 to $715/night

    Hale Ki'i Maka Manu

    4 BedroomsBathroomsSleeps 10
    3 nights minstay
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $152 to $500/night

    Newly Remodeled Corner Unit at the Waikiki Banyan with D...

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $162 to $551/night

    Spacious 14th Floor Corner Suite, Partial Diamond Head a...

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $367 to $464/night

    Turtle Bay Pikake

    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. $421 to $497/night

    Turtle Bay Hanalei

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $396 to $1,728/night

    Wailea Ekahi 34B

    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. $166 to $563/night

    Kihei Kai Nani #8-362

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $208 to $544/night

    Hale Ono Loa 411

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $312 to $1,172/night

    Luana Kai D305

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $324 to $991/night

    Wailea Ekahi 47E

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $258 to $1,026/night

    Big Island Fairway Villa I-33

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $213 to $582/night

    Big Island White Sands Village 228

    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. $3,035 to $12,174/night

    Wailea Beach Villa B102

    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. $231 to $954/night

    Grand Champions 145

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $458 to $1,609/night

    Royal Mauian 204

    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. $469 to $1,785/night

    Big Island Kolea 11C

    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. $281 to $1,305/night

    Grand Champions 130

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $252 to $905/night

    Big Island Sea Village 3212

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $250 to $678/night

    Kamaole Sands 6-104

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $306 to $1,329/night

    Wailea Ekolu 904

    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. $225 to $728/night

    Maui Vista 3410

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $469 to $1,784/night

    Wailea Ekahi 5E

    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. $921 to $4,200/night

    Ho'olei 55-2

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $259 to $758/night

    Pacific Shores B205

    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. $346 to $1,112/night

    Wailea Ekahi 48E

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $1,152 to $5,339/night

    Ho'olei 17-1

    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. $274 to $841/night

    Kauai Regency at Poipu Kai #811

    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. $923 to $4,073/night

    Ho'olei 24-1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $414 to $1,343/night

    Palms at Wailea 403

    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. $701 to $3,465/night

    Wailea Elua 2305

    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. $260 to $1,027/night

    Big Island Waikoloa Colony Villas 2404

    2 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $549 to $1,917/night

    Big Island Kona Reef D-21

    3 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. $184 to $368/night

    Kona Coast Resort at Keauhou Gardens 8204

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $1,155 to $1,680/night

    Turtle Rock

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $152 to $263/night

    Alii Villas 340

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $131 to $525/night

    Kona Plaza#402

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $135 to $247/night

    Keauhou Akahi 210

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $152 to $315/night

    Kahaluu Bay Villas #304

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $184 to $368/night

    Kona Isle E23

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $161 to $328/night

    Kona Makai 2-102

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $263 to $378/night

    Hale O' Waikoloa

    3 Bedrooms2.5 BathroomsSleeps 7
    5 nights minstay
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $209 to $394/night

    Keauhou Kona Surf & Racquet Club#6-101

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