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. $17,975 to $27,561/night

    Kauhale Pilialoha

    10 Bedrooms14 BathroomsSleeps 30
    6 nights minstay
    Pool Hot Tub
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  3. $10,240 to $12,620/night

    Mauna Kea Bluffs #5: La Ikena O Komohana*

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
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  5. $5,369/night

    Ocean Views from Heliconia 2302 Residences

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pool Hot Tub
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  7. $5,244/night

    Honua kai Konea 642/643 4 bedroom/4 bath

    4 BedroomsBathroomsSleeps 12
    3 nights minstay
    Pool Hot Tub
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  9. $4,366 to $6,238/night

    Hanalei Beach House Estate

    5 BedroomsBathroomsSleeps 11
    3 nights minstay
    FREE CANCELLATION
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  11. $4,314/night

    Maui Westside Properties- 3 Bed Penthouse K1019

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pool Hot Tub
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  13. $4,194/night

    Kalina at Hapuna Beach

    4 Bedrooms4.5 BathroomsSleeps 10
    5 nights minstay
    Pool Hot Tub
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  15. $3,743 to $7,485/night

    Lani Kai

    4 BedroomsBathroomsSleeps 8
    3 nights minstay
    Hot Tub
    FREE CANCELLATION
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  17. $3,695 to $6,075/night

    Mauna Kea Resort Bluffs 22- The Beach House

    4 Bedrooms5.5 BathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
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  19. $3,695 to $7,265/night

    Mauna Kea Resort Bluffs 22- The Beach House

    4 Bedrooms5.5 BathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
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  21. $3,327/night

    Sans Souci PH2

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    FREE CANCELLATION
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  23. $3,248 to $5,568/night

    Wailea Inn Maui

    14 Bedrooms13 BathroomsSleeps 32
    2 nights minstay
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  25. $3,141/night

    Maui Westside Properties- K501 Amazing 2 Bed

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
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  27. $3,119/night

    Sans Souci 107

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    FREE CANCELLATION
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  29. $2,900 to $3,088/night

    Hale Nui

    5 Bedrooms5.5 BathroomsSleeps 10
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  30. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  31. $2,852 to $3,743/night

    Dolphin House

    6 BedroomsBathroomsSleeps 10
    7 nights minstay
    FREE CANCELLATION
  32. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  33. $2,743 to $6,408/night

    Blue Lagoon*

    7 BedroomsBathroomsSleeps 14
    2 nights minstay
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  35. $2,732/night

    Maui Westside Properties: K301 Amazing 2 Bed W/BBQ

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
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  37. $2,673 to $3,119/night

    Blue Mahina at Sunset Beach

    4 BedroomsBathroomsSleeps 11
    7 nights minstay
    FREE CANCELLATION
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $2,505 to $4,766/night

    Mauna Kea Resort Townhouse- Kaunaoa 7B (4BR/4.5BA)

    4 Bedrooms4.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
  40. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  41. $2,495 to $4,990/night

    Hanalei Beachfront

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    FREE CANCELLATION
  42. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  43. $2,413 to $3,119/night

    Sans Souci 605/606

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    FREE CANCELLATION
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  45. $2,413/night

    Sans Souci 1107

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    FREE CANCELLATION
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  47. $2,413/night

    Sans Souci 403/404

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    FREE CANCELLATION
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  49. $2,413/night

    Sans Souci 807

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    FREE CANCELLATION
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  51. $2,318 to $2,495/night

    Helen's Beach House

    6 BedroomsBathroomsSleeps 14
    7 nights minstay
    Pool
    FREE CANCELLATION
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $2,318 to $2,495/night

    Kailua Beachside

    4 BedroomsBathroomsSleeps 14
    7 nights minstay
    Pool
    FREE CANCELLATION
  54. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  55. $2,288/night

    Sans Souci 607

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    FREE CANCELLATION
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $2,288/night

    Colony Surf 601

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $2,288/night

    Colony Surf 504

    2 BedroomsBathroomsSleeps 2
    3 nights minstay
    FREE CANCELLATION
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $2,210/night

    Maui Westside Properties- Honua Kai-H836

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $2,203 to $3,457/night

    4BD Villas at Mauna Kea #21

    4 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $2,115 to $3,743/night

    Napili Ocean Front House 43

    5 BedroomsBathroomsSleeps 10
    5 nights minstay
    Hot Tub
    FREE CANCELLATION
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $2,080 to $2,495/night

    Colony Surf 104

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $2,080/night

    Colony Surf 1402

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $2,041/night

    Maui Westside Properties: Honua kai- Konea 643

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $2,041/night

    Maui Westside Properties: Honua Kai- Konea 642

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $1,997/night

    Maui Westside Properties- Hokulani 306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $1,995 to $3,392/night

    Luxury 6 bedroom Penthouse w/ Pool & Hot Tub- Steps ...

    6 BedroomsBathroomsSleeps 16
    2 nights minstay
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $1,986 to $4,025/night

    Hale Pua

    5 BedroomsBathroomsSleeps 16
    2 nights minstay
    Pool Hot Tub
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $1,955/night

    Sans Souci 604

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $1,955/night

    Sans Souci 304

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $1,955/night

    Sans Souci 1201

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $1,955/night

    Sans Souci 701

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $1,955/night

    Sans Souci 1004

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $1,955/night

    Sans Souci 1105

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $1,955/night

    Sans Souci 204

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $1,955/night

    Sans Souci 201

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $1,912/night

    Maui Westside Presents: Honua kai- Konea 1026

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $1,900 to $2,138/night

    Makena Aloha Estate

    4 BedroomsBathroomsSleeps 10
    5 nights minstay
    Pool Hot Tub
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $1,871 to $1,955/night

    Colony Surf 201

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $1,871 to $2,080/night

    Colony Surf 102

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $1,871/night

    Colony Surf 1202

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $1,871/night

    Weke Road Beachfront Cottage

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $1,871 to $2,339/night

    Pinetrees Beach Villa

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $1,871 to $3,493/night

    Waiakalua

    4 BedroomsBathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $1,871 to $3,119/night

    Hale I'a U'i- Beautiful Fish House

    4 Bedrooms5.5 BathroomsSleeps 10
    3 nights minstay
    Hot Tub
    FREE CANCELLATION
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $1,870 to $2,494/night

    Wilikoki House

    6 BedroomsBathroomsSleeps 10
    5 nights minstay
    FREE CANCELLATION
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $1,839/night

    Colony Surf 809

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $1,830 to $2,703/night

    Colony Surf 1207

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $1,830/night

    Sans Souci 805

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $1,797 to $2,217/night

    Hale Waiulu

    3 Bedrooms3.5 BathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $1,780/night

    Hale Lani

    4 BedroomsBathroomsSleeps 14
    3 nights minstay
    Pool
    FREE CANCELLATION
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $1,761 to $2,076/night

    WAILEA ELUA, #1305^

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool Hot Tub
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $1,747/night

    Colony Surf 1005

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $1,695 to $3,743/night

    Hale Maluhia Hanalei

    1 Bedroom1.5  BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $1,692 to $2,494/night

    Rainbow Hale Estate

    4 Bedrooms3.5 BathroomsSleeps 8
    5 nights minstay
    Pool
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $1,672 to $2,981/night

    Champion Ridge Home

    4 Bedrooms4.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $1,664/night

    Colony Surf 1909

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $1,664/night

    Colony Surf 1905

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $1,664/night

    Colony Surf 1409

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $1,664 to $2,288/night

    Colony Surf 609

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $1,664/night

    Sans Souci 804

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $1,664/night

    Colony Surf 1807

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $1,664/night

    Colony Surf 401

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $1,651/night

    Maui Westside- Kaanapali Shores 259 Ocean Front!

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $1,649 to $2,468/night

    INDO LOTUS BEACH HOUSE

    4 BedroomsBathroomsSleeps 8
    5 nights minstay
    Hot Tub
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $1,646 to $5,733/night

    3BD Golf Villa (3101 Kumukehu) at Four Seasons Resort Hu...

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $1,613 to $3,219/night

    Hillside Villa 7101

    3 Bedrooms BathroomSleeps 6
    2 nights minstay
    Pool
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $1,605 to $5,285/night

    5BD Estate Home Fairways South #18 at Mauna Kea Resort

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $1,581/night

    Colony Surf 1702

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $1,559 to $3,431/night

    Ikena Lani

    5 BedroomsBathroomsSleeps 12
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $1,553 to $3,398/night

    Laulea Kailani Villa (KAUAI)

    3 Bedrooms3.5 BathroomsSleeps 6
    2 nights minstay
    Pool
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $1,553 to $4,898/night

    Haena Beach House TVNC#1258

    5 BedroomsBathroomsSleeps 10
    2 nights minstay
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $1,504/night

    Maui Westside- Presents- Honua kai- Konea 312

    2 Bedrooms BathroomSleeps 6
    3 nights minstay
    Pool Hot Tub
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $1,497 to $2,495/night

    Huaka Mahina

    4 Bedrooms4.5 BathroomsSleeps 8
    5 nights minstay
    Pool
    FREE CANCELLATION
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $1,497 to $2,139/night

    Laau Paina

    5 BedroomsBathroomsSleeps 10
    7 nights minstay
    FREE CANCELLATION
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $1,497 to $2,495/night

    Leimoku

    5 Bedrooms4.5 BathroomsSleeps 10
    7 nights minstay
    FREE CANCELLATION
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $1,456/night

    Colony Surf 207

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $1,456/night

    Colony Surf 403

    Studio BathroomSleeps 2
    3 nights minstay
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $1,434 to $5,225/night

    Mermaid Cove

    4 BedroomsBathroomsSleeps 13
    2 nights minstay
    Pool Hot Tub
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $1,434 to $3,267/night

    Blue Oasis*

    5 BedroomsBathroomsSleeps 14
    2 nights minstay
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $1,434 to $3,267/night

    Blue Oasis

    5 BedroomsBathroomsSleeps 14
    2 nights minstay
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $1,434 to $3,100/night

    Ka'ulu Villa 129B

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $1,413 to $1,906/night

    Moloa'a Bay Villa and Cottage

    5 BedroomsBathroomsSleeps 12
    3 nights minstay
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $1,395/night

    Kona Bubbles

    4 Bedrooms4.5 BathroomsSleeps 8
    7 nights minstay
    Pool
    FREE CANCELLATION
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $1,375 to $3,537/night

    Kona Blue

    5 Bedrooms3.5 BathroomsSleeps 13
    2 nights minstay
    Pool
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $1,374/night

    Maui Westside Properties- MAUI ELDORADO D200

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $1,373 to $3,976/night

    House of the Turtle at Champion Ridge, Mauna Lani (CR 18...

    4 Bedrooms4.5 BathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $1,372/night

    Sans Souci 1106

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