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  1. $3,105 to $8,050/night

    Beach Castle

    7 BedroomsBathroomsSleeps 18
    3 nights minstay
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  3. $3,035 to $10,816/night

    Wailea Beach Villa B102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  5. $2,811 to $9,598/night

    Wailea Beach Villa B202

    3 Bedrooms3.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  7. $2,532 to $9,183/night

    Andaz Villa 810

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  9. $1,846 to $5,684/night

    Halama Hale Private Home

    4 Bedrooms3.5 BathroomsSleeps 14
    2 nights minstay
    Pool
    FREE CANCELLATION
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  11. $1,224 to $3,162/night

    Seaside Serenity Oceanfront Luxury with Pool

    6 Bedrooms7.5 BathroomsSleeps 15
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  13. $1,220 to $3,736/night

    Big Island Hale Kaheka 6592

    1 Bedroom2.5 BathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  15. $1,096 to $4,770/night

    Wailea Beach Villa I503

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  17. $1,038 to $3,624/night

    Wailea Beach Villa H202

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  19. $1,017 to $3,497/night

    Anahola Aloha Beach House

    4 BedroomsBathroomsSleeps 12
    3 nights minstay
    Hot Tub
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  21. $989 to $2,806/night

    Honua Kai Konea 250

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  23. $936 to $1,411/night

    Sands Of Kahana 384

    1 BedroomBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
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  25. $923 to $2,559/night

    Polo Beach Club 106

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  27. $923 to $2,294/night

    Big Island Holua Kai 7061

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  29. $808 to $2,779/night

    Wailea Beach Villa J106

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  31. $767 to $2,779/night

    Wailea Beach Villa H102

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  33. $742 to $2,062/night

    Sands Of Kahana PH 381 3Bd/3Ba OF

    3 BedroomsBathroomsSleeps 10
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
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  35. $735 to $1,516/night

    Hale Lani

    1 Bedroom BathroomSleeps 2
    2 nights minstay
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  37. $721 to $2,281/night

    Noelani 306

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  39. $701 to $3,238/night

    Wailea Elua 2305

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  41. $668 to $2,499/night

    Makena Surf B305

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  43. $659 to $1,956/night

    Noelani 307

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  45. $656 to $2,791/night

    Polo Beach Club 107

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  47. $626 to $2,485/night

    Breeze Away- 2525 Bienville Blvd

    5 BedroomsBathroomsSleeps 20
    2 nights minstay
    Pool Pets OK
    FREE CANCELLATION
  48. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  49. $626 to $2,360/night

    Lemon Breeze- 2521 Bienville

    5 BedroomsBathroomsSleeps 25
    3 nights minstay
    Pool Pets OK
    FREE CANCELLATION
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  51. $621 to $1,116/night

    Kahana Sunset A7

    2 Bedrooms2.5 BathroomsSleeps 6
    4 nights minstay
    Pool
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  53. $606 to $2,149/night

    Makena Surf A204

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  55. $604 to $2,732/night

    Makena Surf F201

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $603 to $2,137/night

    Kauai Poipu Kapili 51

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
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  59. $578 to $1,319/night

    75 San Antonia

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    FREE CANCELLATION
  60. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  61. $577 to $1,508/night

    Mana Kai #403

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
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  63. $577 to $1,956/night

    Wailea Ekahi 48A

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  65. $567 to $907/night

    South Beach 501

    3 Bedrooms3.5 BathroomsSleeps 6
    7 nights minstay
    Pool
    FREE CANCELLATION
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  67. $554 to $1,672/night

    Mana Kai #705

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  69. $550 to $1,893/night

    Tidal Wave- Big and Bold Bayfront Beauty! Perfect for th...

    6 Bedrooms4.5 BathroomsSleeps 17
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  71. $528 to $1,388/night

    Royal Mauian 206

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
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  73. $520 to $3,339/night

    Wailea Beach Villa I204

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  75. $520 to $2,460/night

    Beach Happy- 2609 Bienville

    5 BedroomsBathroomsSleeps 15
    3 nights minstay
    Pool
    FREE CANCELLATION
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  77. $520 to $2,431/night

    Island Time VI- GULF FRONT! Private heated pool- gulf vi...

    5 Bedrooms3.5 BathroomsSleeps 16
    2 nights minstay
    Pool Pets OK
    FREE CANCELLATION
  78. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  79. $520 to $1,924/night

    Wailea Elua 2303

    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. $519 to $1,260/night

    Mana Kai #203

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  82. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  83. $493 to $1,117/night

    Noelani 304 3 Bedroom/2.5 Bath Condo

    3 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  84. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  85. $493 to $1,117/night

    Noelani 304 3 Bedroom/2.5 Bath Condo

    3 Bedrooms2.5 BathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  86. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  87. $485 to $1,561/night

    Mana Kai #805

    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. $483 to $1,049/night

    Sands Of Kahana 315 2Bd/2Ba Oceanfront

    2 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  90. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  91. $474 to $1,306/night

    Sands Of Kahana 356

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $473 to $940/night

    Sands Of Kahana 234

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  94. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  95. $472 to $817/night

    Sands of Kahana 282 2 Bedroom Condo

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  96. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  97. $469 to $1,816/night

    Big Island Kolea 11C

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $469 to $1,019/night

    Honua Kai 215 2 Bed/2 Bath

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $469 to $1,671/night

    Wailea Ekahi 5E

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  102. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  103. $467 to $677/night

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  104. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  105. $467 to $677/night

    Waipouli Beach Resort G-306

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $467 to $1,338/night

    My Waii Beach Cottage

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    FREE CANCELLATION
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $467 to $1,420/night

    Island Time IV- PET FRIENDLY! Private heated gulf facing...

    5 Bedrooms3.5 BathroomsSleeps 13
    3 nights minstay
    Pool Pets OK
    FREE CANCELLATION
  110. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  111. $467 to $677/night

    Waipouli Beach Resort G-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $467 to $677/night

    Waipouli Beach Resort G-404

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $467 to $1,329/night

    Mana Kai #815

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $466 to $1,570/night

    Kauai Kiahuna Plantation #64

    Multiple Units Available
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $458 to $1,475/night

    Royal Mauian 204

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $454 to $847/night

    Beach Villa Two Bedroom B1813A+

    2 BedroomsBathroomsSleeps 4
    4 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $451 to $1,115/night

    Papakea H404 3 bedroom condo

    3 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $449 to $1,928/night

    Wave Louder- Gulf view beach house with NEW private HEAT...

    5 BedroomsBathroomsSleeps 14
    3 nights minstay
    Pool Pets OK
    FREE CANCELLATION
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $428 to $688/night

    Del Mar Gem

    2 BedroomsBathroomsSleeps 4
    30 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $426 to $1,332/night

    Big Island Kona Bali Kai 301

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $425 to $1,461/night

    Sonny Side- Enjoy the private and personal lot space for...

    4 BedroomsBathroomsSleeps 10
    3 nights minstay
    Pool Pets OK
    FREE CANCELLATION
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $420 to $1,306/night

    Sands of Kahana 366

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool Hot Tub
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $415 to $985/night

    Sands of Kahana 255

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  136. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  137. $414 to $1,306/night

    Sands Of Kahana 215

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $410 to $1,205/night

    Kauai Pili Mai 14J

    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. $404 to $1,306/night

    Sands Of Kahana 272

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $404 to $1,441/night

    Mana Kai #508

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $404 to $1,058/night

    Mana Kai #412

    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. $404 to $1,120/night

    Maui Sunset B217

    2 BedroomsBathroomsSleeps 7
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $404 to $734/night

    Single Family Bay Home C82B

    3 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub Pets OK
    FREE CANCELLATION
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $403 to $1,289/night

    Kamaole Nalu 504

    Multiple Units Available
    2 nights minstay
    Pool
    FREE CANCELLATION
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $396 to $796/night

    Beach Villa Two Bedroom B1311A

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  154. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  155. $396 to $796/night

    Beach Villa Two Bedroom B3712A

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $393 to $1,468/night

    W Residences 2 Bedroom Suite "Endless Summer"

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
  158. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  159. $392 to $985/night

    Sands Of Kahana 334

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $391 to $1,520/night

    Big Island Kolea 14H

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $390 to $1,655/night

    Pelicans Perch- Half Acre Private lot directly on the gu...

    4 BedroomsBathroomsSleeps 15
    2 nights minstay
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $388 to $572/night

    Waipouli Beach Resort E-205

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $387 to $1,266/night

    207 Margate

    4 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $387 to $1,266/night

    2507 Margate- 4 bedroom ocean front condo-

    4 BedroomsBathroomsSleeps 10
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $384 to $1,182/night

    The Blue Crab- BAYFRONT! Private Pool- steps to the beac...

    4 BedroomsBathroomsSleeps 12
    2 nights minstay
    FREE CANCELLATION
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $378 to $1,420/night

    Strand Castle- GULF FRONT! An ideal layout with game roo...

    4 Bedrooms3.5 BathroomsSleeps 14
    2 nights minstay
    Pool
    FREE CANCELLATION
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $372 to $485/night

    Kona Palms 304

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  177. $372 to $2,366/night

    High Tide- PET FRIENDLY! Expansive floor plan and stunni...

    6 BedroomsBathroomsSleeps 14
    3 nights minstay
    Pets OK
    FREE CANCELLATION
  178. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  179. $371 to $877/night

    Kahana Village 40 Oceanfront 2Bed/2Bath

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
    FREE CANCELLATION
  180. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  181. $368 to $887/night

    Papakea K406 OceanView 2 Bedroom 2 bath

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  182. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  183. $362 to $572/night

    Waipouli Beach Resort C-105

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
  184. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  185. $362 to $572/night

    Waipouli Beach Resort C-205

    2 BedroomsBathroomsSleeps 5
    3 nights minstay
    Pool Hot Tub
  186. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  187. $360 to $1,218/night

    Dauphin Charm- GULF FRONT! Pet Friendly- wrap around por...

    4 BedroomsBathroomsSleeps 12
    2 nights minstay
    Pets OK
    FREE CANCELLATION
  188. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  189. $360 to $1,241/night

    Shamrock Shores- GULF FRONT west end PET FRIENDLY proper...

    6 BedroomsBathroomsSleeps 16
    3 nights minstay
    Pets OK
    FREE CANCELLATION
  190. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  191. $359 to $985/night

    Sands Of Kahana 353

    2 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool Hot Tub
  192. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  193. $358 to $877/night

    Jen's Creole Cottage

    4 Bedrooms3.5 BathroomsSleeps 8
    3 nights minstay
    FREE CANCELLATION
  194. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  195. $358 to $861/night

    Valley Isle1108- 2 bedroom condo

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
    FREE CANCELLATION
  196. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  197. $357 to $1,249/night

    Wailea Ekahi 40D

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  198. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  199. $357 to $561/night

    Island Princess 604

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  200. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations