RedAwning has 300 South Maui vacation rentals which all include instant online booking and no security deposits, to make your trip easy and stress-free! On this beautiful region of the island, in addition to relaxing on the pristine beaches, such as Wailea, there are plenty of fun activities to partake in, such as surfing in Makena State Park, snorkeling at Maalaea Harbor, joining the Maui Sun Divers to learn how to scuba dive, or going on a Blue Water Rafting snorkel cruise. Book your stay today!

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  1. $241 to $864/night

    WAILEA EKOLU #203

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  3. $168 to $590/night

    THE SHORES OF MAUI #223

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  5. $318 to $426/night

    Sugar Beach #227

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  7. $377 to $458/night

    Kamaole Sands #03-407

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  9. $334 to $444/night

    Sugar Beach #317

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  11. $204 to $353/night

    Kihei Akahi Resort- Unit C516

    1 Bedroom BathroomSleeps 4
    7 nights minstay
    FREE CANCELLATION
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  13. $161 to $289/night

    Kihei Akahi Resort- Unit DG16

    Studio BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
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  15. $398 to $480/night

    Kamaole Sands #10-407

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  17. $304 to $350/night

    Maui Parkshore #306

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
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  19. $356 to $417/night

    Kamaole Sands #08-105

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  21. $296 to $356/night

    Maui Banyan #G-406

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  23. $540 to $613/night

    Kamaole Sands #10-417

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  25. $344 to $460/night

    Kihei Surfside #412

    1 Bedroom1.5  BathroomSleeps 2
    4 nights minstay
    Pool
    FREE CANCELLATION
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  27. $235 to $296/night

    Kihei Akahi #C-608

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  28. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  29. $321 to $390/night

    Kihei Akahi #D-615 (7th Flr)

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
    FREE CANCELLATION
  30. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  31. $152 to $219/night

    Nani Kai Hale # 405

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  32. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  33. $334 to $444/night

    Sugar Beach #132

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  35. $178 to $356/night

    Maui Banyan #H-502

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  36. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  37. $398 to $480/night

    Kamaole Sands #10-410

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  38. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  39. $356 to $417/night

    Kamaole Sands #08-410

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  40. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  41. $305 to $390/night

    Kauhale Makai #132

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  42. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  43. $235 to $296/night

    Kihei Akahi #C-317

    1 Bedroom BathroomSleeps 2
    5 nights minstay
    Pool
    FREE CANCELLATION
  44. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  45. $384 to $488/night

    Maui Kamaole #H-202

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  46. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  47. $235 to $296/night

    Kihei Akahi #C-109

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $257 to $326/night

    Nani Kai Hale #208

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  50. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  51. $246 to $279/night

    Maui Vista #3202

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  52. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  53. $304 to $350/night

    Maui Parkshore #312

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
    FREE CANCELLATION
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  55. $377 to $458/night

    Kamaole Sands #06-310

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $204 to $353/night

    Kihei Akahi Resort- Unit C405

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  58. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  59. $223 to $267/night

    Kihei Akahi #C-401

    Studio BathroomSleeps 2
    4 nights minstay
    Pool
    FREE CANCELLATION
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $141 to $197/night

    Nani Kai Hale # 301

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  62. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  63. $296 to $332/night

    Kamaole Sands #07-306

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  64. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  65. $152 to $219/night

    Nani Kai Hale 307

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  66. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  67. $428 to $546/night

    Maui Kamaole #I-212

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  68. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  69. $318 to $426/night

    Sugar Beach #133

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  70. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  71. $267 to $326/night

    Kauhale Makai #207

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  72. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  73. $143 to $254/night

    Oceanfront 1BR w/ Lanai & Pool

    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. $128 to $222/night

    Sunny 1BR w/ Pool & Balcony- Walk 5 Minutes to Beach...

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  76. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  77. $297 to $390/night

    Maui Kamaole #I-111

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $370 to $466/night

    Maui Banyan #G-209

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  80. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  81. $283 to $330/night

    Kauhale Makai 529

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $246 to $279/night

    Maui Vista #1209

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $239 to $296/night

    Kauhale Makai #122

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $266 to $311/night

    Kamaole Sands #09-102

    1 BedroomBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  88. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  89. $203 to $264/night

    Nani Kai Hale # 308

    1 BedroomBathroomsSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $246 to $279/night

    Maui Vista #1322

    1 Bedroom BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $398 to $480/night

    Kamaole Sands #08-411

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $186 to $320/night

    Kihei Akahi Resort- Unit C313

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    FREE CANCELLATION
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $413 to $528/night

    Grand Champions #033

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $334 to $428/night

    Pacific Shores B406

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $490 to $544/night

    Maui Banyan Q204

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $318 to $363/night

    Kamaole Sands 5-313

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $494 to $644/night

    Pacific Shores B102

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $346 to $469/night

    Kihei Alii Kai A101

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $450 to $586/night

    Wailea Ekolu 1604

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $301 to $424/night

    Maui Sunset B402

    1 BedroomBathroomsSleeps 5
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $291 to $436/night

    Maui Vista 2211

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $359 to $469/night

    Wailea Ekahi 49A

    1 BedroomBathroomsSleeps 2
    2 nights minstay
    Pool
    FREE CANCELLATION
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $406 to $500/night

    Wailea Ekahi 50C

    1 Bedroom BathroomSleeps 3
    2 nights minstay
    Pool
    FREE CANCELLATION
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $354 to $524/night

    Kihei Kai Nani 373

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $663 to $761/night

    Grand Champions 124

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $281 to $334/night

    Maui Parkshore #303

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $344 to $460/night

    Kihei Surfside #210

    1 Bedroom1.5  BathroomSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $281 to $334/night

    Maui Parkshore #409

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool
    FREE CANCELLATION
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $446 to $654/night

    Grand Champions #089

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $377 to $458/night

    Kamaole Sands #05-406

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $297 to $390/night

    Maui Kamaole #B-107

    1 BedroomBathroomsSleeps 4
    7 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $384 to $488/night

    Maui Kamaole #H-207

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $377 to $458/night

    Kamaole Sands #06-405

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $253 to $311/night

    Kauhale Makai #605

    1 Bedroom BathroomSleeps 2
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $258/night

    131

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $340/night

    340

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $258/night

    164

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $258/night

    127

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $340/night

    326

    2 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pool
    FREE CANCELLATION
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $340/night

    308

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $258/night

    155

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $258/night

    213

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $258/night

    107

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $258/night

    144

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $340/night

    221

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $363/night

    249

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $317/night

    311

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool
    FREE CANCELLATION
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $258/night

    156

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $340/night

    273

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $258/night

    207

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $297/night

    171

    1 Bedroom BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $258/night

    217

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $258/night

    209

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $258/night

    218

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $340/night

    266

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $340/night

    264

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
    FREE CANCELLATION
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $317/night

    338

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $188/night

    Maui Banyan T103A

    Studio BathroomSleeps 2
    3 nights minstay
    Pool
    FREE CANCELLATION
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $258/night

    130

    1 Bedroom BathroomSleeps 4
    3 nights minstay
    Pool
    FREE CANCELLATION
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $384 to $488/night

    Maui Kamaole #F-208

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $304 to $467/night

    A3-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $304 to $467/night

    D3-1 Bedroom Beachfront

    1 Bedroom BathroomSleeps 4
    5 nights minstay
    Pool
    FREE CANCELLATION
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $304 to $540/night

    G9-2 Bedroom Oceanfront Townhouse

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool
    FREE CANCELLATION
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $349 to $585/night

    A5-2 Beachfront Loft Suite

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