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. $310 to $624/night

    Bay Villa 24G3

    1 Bedroom1.5  BathroomSleeps 4
    4 nights minstay
    Pool
  2. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  3. $379 to $781/night

    Kahana Sunset B5B

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
  4. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  5. $353 to $624/night

    Kahana Sunset E8

    2 BedroomsBathroomsSleeps 5
    4 nights minstay
    Pool
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  7. $353 to $624/night

    Kahana Sunset D5

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
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  9. $151 to $344/night

    Kuleana 706 1 Bedroom Condo

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
    FREE CANCELLATION
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  11. $118 to $398/night

    Kaanapali Shores 422 1 Bedroom Condo

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  12. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  13. $351 to $1,116/night

    Papakea H404 3 bedroom condo

    3 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  14. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  15. $299 to $976/night

    Maui Banyan T209

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  16. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  17. $282 to $1,592/night

    Wailea Ekolu 502

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  18. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  19. $467 to $1,464/night

    My Waii Beach Cottage

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    FREE CANCELLATION
  20. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  21. $213 to $740/night

    Hale Kamaole 121

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  22. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  23. $485 to $1,700/night

    Mana Kai #805

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  24. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  25. $231 to $830/night

    Maui Vista 2416

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  26. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  27. $357 to $1,586/night

    Wailea Ekolu 908

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  28. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  29. $217 to $624/night

    Kahana Sunset E6

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
  30. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  31. $224 to $909/night

    Grand Champions 141

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  32. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  33. $802 to $3,792/night

    Ho'olei 24-2

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  34. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  35. $289 to $980/night

    Wailea Ekahi 49F

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  36. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  37. $345 to $1,362/night

    Grand Champions 137

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $981 to $4,337/night

    Ho'olei 21-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  40. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  41. $224 to $876/night

    Kihei Garden Estates D104

    2 Bedrooms BathroomSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  43. $865 to $3,810/night

    Ho'olei 12-4

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $170 to $311/night

    Island Surf 402

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
  46. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  47. $656 to $2,986/night

    Polo Beach Club 107

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $254 to $752/night

    Sugar Beach Resort 209

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  50. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  51. $163 to $624/night

    Kahana Sunset D8

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $370 to $1,129/night

    Sands Of Kahana 474

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  54. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  55. $167 to $558/night

    Kahana Sunset D11

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $668 to $2,681/night

    Makena Surf B305

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $3,035 to $11,631/night

    Wailea Beach Villa B102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $701 to $3,474/night

    Wailea Elua 2305

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $110 to $398/night

    Kaanapali Shores 642 Studio Condo

    Studio BathroomSleeps 2
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $291 to $876/night

    Kapalua Ridge Villa 1013 Ocean View

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
    FREE CANCELLATION
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $163 to $624/night

    Mahana At Kaanapali 306

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $396 to $1,724/night

    Wailea Ekahi 34B

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $1,038 to $5,013/night

    Ho'olei 17-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $260 to $1,107/night

    Wailea Ekahi 48E

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  74. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  75. $281 to $1,306/night

    Grand Champions 130

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $1,152 to $5,344/night

    Ho'olei 17-1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $250 to $678/night

    Kamaole Sands 6-104

    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. $189 to $624/night

    Kahana Sunset B7

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $259 to $758/night

    Pacific Shores B205

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $324 to $993/night

    Wailea Ekahi 47E

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $225 to $728/night

    Maui Vista 3410

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $469 to $1,789/night

    Wailea Ekahi 5E

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $923 to $4,087/night

    Ho'olei 24-1

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $312 to $1,170/night

    Luana Kai D305

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $231 to $959/night

    Grand Champions 145

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $306 to $1,324/night

    Wailea Ekolu 904

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $921 to $4,211/night

    Ho'olei 55-2

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $166 to $566/night

    Kihei Kai Nani #8-362

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $458 to $1,608/night

    Royal Mauian 204

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $318 to $1,340/night

    Wailea Ekahi 25B

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $1,038 to $4,344/night

    Ho'olei 112-5

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $219 to $650/night

    Kahana Sunset A4

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $137 to $519/night

    Ridge Villa 1222

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $163 to $624/night

    Kahana Sunset D7

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $310 to $940/night

    Sands Of Kahana 234

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $134 to $470/night

    Kahana Sunset C1C

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $329 to $1,306/night

    Sands of Kahana 366

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $134 to $492/night

    Whaler On Kaanapali 763

    Studio BathroomSleeps 4
    3 nights minstay
    Pool Hot Tub
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $251 to $730/night

    Kahana Sunset B6

    2 BedroomsBathroomsSleeps 5
    4 nights minstay
    Pool
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $474 to $1,306/night

    Sands Of Kahana 356

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $175 to $387/night

    Royal Kahana 602

    Studio BathroomSleeps 4
    4 nights minstay
    Pool
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $310 to $1,306/night

    Sands Of Kahana 272

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $194 to $558/night

    Bay Villa 11G2

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $936 to $1,411/night

    Sands Of Kahana 384

    1 BedroomBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $621 to $1,116/night

    Kahana Sunset A7

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $145 to $505/night

    Golf Villa 19T4

    1 Bedroom1.5  BathroomSleeps 4
    4 nights minstay
    Pool
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $227 to $656/night

    Ridge Villa 414

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $163 to $624/night

    Kahana Sunset D9

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $132 to $444/night

    Kahana Villa F406 1 Bedroom Condo

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $250 to $688/night

    Honua Kai Hokulani 316 1 Bedroom Condo

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $156 to $473/night

    Napili Shores G157 Studio Condo

    1 Bedroom BathroomSleeps 2
    1 night minstay
    Pool
    FREE CANCELLATION
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $205 to $940/night

    Bay Villa 37G4

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $310 to $1,306/night

    Sands Of Kahana 215

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $124 to $473/night

    Sands Of Kahana 122

    1 BedroomBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $243 to $692/night

    Kahana Reef 120

    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. $279 to $1,295/night

    Wailea Ekolu 1705

    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. $172 to $496/night

    Kihei Akahi C-317

    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. $223 to $647/night

    Maui Kamaole C105

    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. $204 to $643/night

    Kihei Akahi C-507

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $134 to $470/night

    Kahana Sunset B1B

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $404 to $1,571/night

    Mana Kai #508

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $716 to $2,130/night

    Wailea Elua 2109

    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. $300 to $1,243/night

    Wailea Ekahi 45A

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $203 to $672/night

    Maalaea Banyans 104

    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. $233 to $752/night

    Pacific Shores A211

    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. $192 to $541/night

    Kihei Akahi C-612

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $923 to $4,451/night

    Ho'olei 24-4

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $243 to $1,093/night

    Kamaole Sands 7-410

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $767 to $2,974/night

    Wailea Beach Villa H102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $923 to $3,670/night

    Ho'olei 55-3

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $220 to $681/night

    Kamaole Sands 6-102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $414 to $1,224/night

    Palms at Wailea 206

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $273 to $1,198/night

    Grand Champions 35

    2 BedroomsBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $866 to $3,860/night

    Ho'olei 24-6

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $289 to $970/night

    Wailea Ekahi 36B

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $299 to $935/night

    Maui Parkshore 315

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $433 to $1,372/night

    Palms at Wailea 2104

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