RedAwning has over 350 Maui vacation homes and condos which all include instant online booking and no security deposits, to make your trip easy and stress-free. Maui is home to some of Hawaii’s most beautiful beaches and offers plenty of opportunities for adventure, from snorkeling with turtles to hiking through the bamboo forest to cliff diving in Hana. Book your stay today!

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  1. $366 to $393/night

    Hale Kamaole 271

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
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  3. $304 to $540/night

    F5-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
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  5. $304 to $540/night

    E5-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  6. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  7. $846 to $4,363/night

    Maui Westside Properties- 3 Bed Penthouse K1019

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  8. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  9. $335 to $1,805/night

    Maui Westside Properties: Honua Kai- Konea 642

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  10. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  11. $270 to $1,805/night

    Maui Westside Presents: Honua kai- Konea 1026

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
  12. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  13. $197 to $632/night

    Maui Kaanapali Villas #B247

    Studio BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
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  15. $278 to $754/night

    Lahaina Roads #405

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
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  17. $181 to $365/night

    Maui Kaanapali Villas #A517

    Studio BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  18. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  19. $197 to $557/night

    Maui Kaanapali Villas #A317

    Studio BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
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  21. $357 to $800/night

    Kaanapali Shores #159

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
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  23. $247 to $542/night

    Whaler #656

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
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  25. $348 to $980/night

    Kaanapali Shores #255

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
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  27. $194 to $499/night

    Maui Eldorado Condo K207

    Studio BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
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  29. $259 to $493/night

    Mahana Resort #813

    Studio BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  30. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  31. $216 to $363/night

    Hale Kamaole 276

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
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  33. $428 to $484/night

    Kahana Sunset F4

    2 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool
  34. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  35. $215 to $491/night

    Papakea #F105

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
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  37. $297 to $669/night

    Honua Kai-Hokulani #218

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $371 to $1,264/night

    Papakea #A201

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  40. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  41. $331 to $806/night

    Maui Eldorado Condo D100

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
    FREE CANCELLATION
  42. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  43. $377 to $591/night

    E4-2 Bedroom Oceanfront

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $259 to $428/night

    G4-1 Bedroom Oceanfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
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  47. $259 to $428/night

    E3-1 Bedroom Oceanfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $209 to $684/night

    Kaanapali Royal #E302

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
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  51. $1,224 to $1,698/night

    Kaanapali Alii 456

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $563 to $1,044/night

    Kaanapali Shores 403

    2 BedroomsBathroomsSleeps 7
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  55. $335 to $478/night

    Honokeana Cove 103

    1 Bedroom BathroomSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $215 to $934/night

    Lahaina Shores #317

    Studio BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $302 to $354/night

    Unit 311

    2 BedroomsBathroomsSleeps 5
    5 nights minstay
    Pool
    FREE CANCELLATION
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $196 to $284/night

    Unit 109

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    FREE CANCELLATION
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  63. $196 to $284/night

    Unit 108

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
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  65. $249 to $302/night

    Unit 114

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    FREE CANCELLATION
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $249 to $302/night

    Unit 214

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    FREE CANCELLATION
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $174 to $365/night

    Maui Kaanapali Villas #A116

    Studio BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $235 to $317/night

    Hale Kamaole 342

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $188 to $258/night

    Hale Kamaole 128

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $258 to $340/night

    Hale Kamaole 336

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $188 to $258/night

    Hale Kamaole 205

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $188 to $258/night

    Hale Kamaole 142

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $188 to $258/night

    Hale Kamaole 152

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $188 to $258/night

    Hale Kamaole 147

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $188 to $258/night

    Hale Kamaole 113

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $258 to $340/night

    Hale Kamaole 330

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $305/night

    Hale Kamaole 170

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $235 to $317/night

    Hale Kamaole 329

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $188 to $258/night

    Hale Kamaole 133

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $188 to $258/night

    Hale Kamaole 237

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $258 to $340/night

    Hale Kamaole 344

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $188 to $258/night

    Hale Kamaole 146

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $188 to $258/night

    Hale Kamaole 172

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $305/night

    Hale Kamaole 174

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $276 to $297/night

    Hale Kamaole 236

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $188 to $258/night

    Hale Kamaole 240

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $188 to $258/night

    Hale Kamaole 220

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $366 to $393/night

    Hale Kamaole 309

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $258 to $340/night

    Hale Kamaole 222

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $235 to $317/night

    Hale Kamaole 268

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $305/night

    Hale Kamaole 176

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $188 to $258/night

    Hale Kamaole 117

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $287 to $366/night

    Hale Kamaole 202

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $181 to $427/night

    Maui Sands #5F

    2 Bedrooms BathroomSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $307 to $1,015/night

    Mahana Resort #1107

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $203 to $276/night

    Nani Kai Hale # 502

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $350 to $613/night

    Maui Kai 601

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $141 to $208/night

    Nani Kai Hale # 601

    1 BedroomBathroomsSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $225 to $398/night

    Napili Shores D229

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $188 to $258/night

    Hale Kamaole 141

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $1,995 to $3,392/night

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

    6 BedroomsBathroomsSleeps 16
    2 nights minstay
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $3,248 to $5,568/night

    Wailea Inn Maui

    14 Bedrooms13 BathroomsSleeps 32
    2 nights minstay
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $463 to $786/night

    Ohana Hale 2 bed/2bath w/ Pool & Hot Tub- Steps To B...

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $235 to $397/night

    Aina Nalu A 201

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $1,900 to $2,969/night

    Makena Aloha Estate

    4 BedroomsBathroomsSleeps 10
    5 nights minstay
    Pool Hot Tub
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $251 to $432/night

    Kuleana 622 1Bdrm

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $158 to $293/night

    Maui Banyan T103

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $121 to $239/night

    Aina Nalu K 205

    1 Bedroom BathroomSleeps 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. $133 to $241/night

    Lil Grass Shack-103

    Studio BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $2,336 to $5,088/night

    Hale Nui

    5 Bedrooms5.5 BathroomsSleeps 10
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $618 to $1,541/night

    Mahana 701

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $268 to $469/night

    Keawakapu 208

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
    FREE CANCELLATION
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $163 to $370/night

    Honua Kai 322

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $151 to $218/night

    Kihei Akahi D604

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $315/night

    Plantation Style Kaanapali Cottage

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $151 to $221/night

    Maui Sunset B204

    1 BedroomBathroomsSleeps 5
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $251 to $441/night

    Island Surf 614

    2 BedroomsBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $899/night

    Kahana Outrigger #1A2

    3 BedroomsBathroomsSleeps 8
    5 nights minstay
    Pool
    FREE CANCELLATION
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $361 to $438/night

    1 Bedroom Oceanfront #604

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $295 to $361/night

    Junior Suite Oceanfront #706

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $394 to $471/night

    1 Bedroom Corner Oceanfront #808

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $295 to $361/night

    Junior Suite Oceanfront #303

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $295 to $361/night

    Junior Suite Oceanfront #702

    Studio BathroomSleeps 3
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $760 to $1,699/night

    Elua Lani 803

    3 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $281 to $719/night

    Maui Eldorado Condo J206

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $186 to $499/night

    Maui Eldorado Condo G203

    Studio BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $186 to $499/night

    Maui Eldorado Condo G201

    Studio BathroomSleeps 3
    1 night minstay
    Pool
    FREE CANCELLATION
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $356 to $869/night

    Maui Eldorado Condo D108

    2 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool
    FREE CANCELLATION
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $281 to $688/night

    Maui Eldorado Condo K212

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $206 to $499/night

    Maui Eldorado Condo J221

    Studio BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $249 to $599/night

    Maui Eldorado Condo B102

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $249 to $624/night

    Maui Eldorado Condo F101

    1 BedroomBathroomsSleeps 5
    1 night minstay
    Pool
    FREE CANCELLATION
  200. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations