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  1. $112 to $284/night

    Discount for longer Stays! Breezy Coastal Vibes

    2 Bedrooms1.5  BathroomSleeps 4
    1 night minstay
    FREE CANCELLATION
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  3. $841 to $1,529/night

    Seaside Haven

    4 BedroomsBathroomsSleeps 8
    7 nights minstay
    Pool
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  5. $253 to $459/night

    1 Step Closer

    2 BedroomsBathroomsSleeps 6
    5 nights minstay
    Pool Pets OK
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  7. $330 to $574/night

    7 Doors Down

    3 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool Pets OK
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  9. $321 to $574/night

    Manatee Manor

    2 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
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  11. $214 to $383/night

    Island Gem B

    2 Bedrooms BathroomSleeps 4
    1 night minstay
    Pool Pets OK
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  13. $330 to $574/night

    Sapphire Beach House

    3 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Pets OK
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  15. $330 to $574/night

    Ebb Tide

    3 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool Pets OK
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  17. $459 to $1,033/night

    Coral Beach

    4 BedroomsBathroomsSleeps 8
    6 nights minstay
    Pool
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  19. $214 to $383/night

    Sea Pirate 5

    2 Bedrooms BathroomSleeps 4
    7 nights minstay
    Pool
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  21. $214 to $383/night

    The Getaway

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
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  23. $204 to $285/night

    Sandy Cove Oasis

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  25. $295 to $642/night

    Crescent Siesta Key Charmer

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  27. $459 to $663/night

    Decked Out on Marbury

    4 Bedrooms4.5 BathroomsSleeps 10
    2 nights minstay
    Pool Pets OK
    FREE CANCELLATION
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  29. $134 to $291/night

    Beach Way Getaway

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
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  31. $183 to $281/night

    Sea Winds on Siesta

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  33. $139 to $240/night

    Sunset Sanctuary

    2 BedroomsBathroomsSleeps 4
    7 nights minstay
    FREE CANCELLATION
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  35. $282 to $611/night

    The Windward House

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Pets OK
    FREE CANCELLATION
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  37. $216 to $459/night

    Just Beachy

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  39. $459 to $994/night

    Bayside Bliss

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pool Pets OK
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  41. $192 to $294/night

    Bay Winds 113

    3 BedroomsBathroomsSleeps 6
    28 nights minstay
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  43. $624 to $1,040/night

    Gulf-View Condo with Resort-Style Amenities

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
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  45. $146 to $268/night

    The Villas 2A

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
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  47. $306 to $498/night

    Coconut Breeze

    2 BedroomsBathroomsSleeps 4
    7 nights minstay
    Pool Pets OK
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  49. $459 to $765/night

    The Salted Coconut

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool
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  51. $345 to $688/night

    The Palm Leaf

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
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  53. $153 to $299/night

    Minnow 2

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
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  55. $465 to $930/night

    Captivated by the Sea

    2 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool
    FREE CANCELLATION
  56. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  57. $345 to $688/night

    Canario Cottage

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
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  59. $345 to $765/night

    Coconut Cottage

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
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  61. $345 to $765/night

    Mermaid's Treasure

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Hot Tub
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  63. $345 to $688/night

    Gladiolus on the Water

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
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  65. $153 to $299/night

    Island Gem A

    2 Bedrooms BathroomSleeps 4
    3 nights minstay
    Pets OK
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  67. $330 to $574/night

    SeaStar Villa

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool
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  69. $459 to $841/night

    The Bea's Knees

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
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  71. $535 to $910/night

    Villa Livella

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
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  73. $214 to $383/night

    The Villas 2B

    2 Bedrooms BathroomSleeps 4
    7 nights minstay
    Pool
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  75. $910 to $1,070/night

    Jersey Girl

    5 BedroomsBathroomsSleeps 10
    3 nights minstay
    Pool
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  77. $214 to $383/night

    Coquina Cottage B

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
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  79. $153 to $299/night

    Mermaid Tale

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pets OK
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  81. $345 to $688/night

    Maritime Memories

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pool Pets OK
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  83. $214 to $383/night

    Hidden Pearl

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
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  85. $345 to $688/night

    Bean Point Bliss

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
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  87. $330 to $574/night

    Hammock Landing

    4 BedroomsBathroomsSleeps 8
    3 nights minstay
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  89. $251 to $407/night

    Crystal Sands on Siesta

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
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  91. $352 to $765/night

    Uptown Luxury on Audubon

    4 Bedrooms3.5 BathroomsSleeps 10
    3 nights minstay
    Hot Tub Pets OK
    FREE CANCELLATION
  92. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  93. $183 to $336/night

    Imperial Sunsets on Siesta

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  95. $91 to $158/night

    Beneva Brooke Beauty

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  97. $207 to $387/night

    Hawk's Sea Nest

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
  98. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  99. $153 to $332/night

    It's a Shore Thing

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  100. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  101. $130 to $487/night

    Las Hermanas 4

    Studio BathroomSleeps 2
    2 nights minstay
    FREE CANCELLATION
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  103. $169 to $281/night

    Salty Soldi

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  105. $216 to $459/night

    Beach Haven

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
  106. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  107. $136 to $306/night

    Siesta Bayside Bliss

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  108. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  109. $192 to $268/night

    Sunbow Bay 108

    2 BedroomsBathroomsSleeps 4
    28 nights minstay
    Pool
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  111. $111 to $462/night

    Private Cozy Sarasota Home

    3 BedroomsBathroomsSleeps 6
    1 night minstay
    FREE CANCELLATION
  112. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  113. $624 to $1,040/night

    Magnificent Gulf View Condo in Shipp's Landing

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
  114. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  115. $421 to $651/night

    The Shady Mermaid

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
  116. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  117. $803 to $1,338/night

    Tiki By The Sea

    5 BedroomsBathroomsSleeps 10
    7 nights minstay
    Pool Hot Tub
  118. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  119. $284 to $498/night

    Blue Water Escape

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
  120. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  121. $321 to $574/night

    Tarpon Pointe

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
  122. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  123. $330 to $651/night

    Splash of Lime

    3 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool Hot Tub Pets OK
  124. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  125. $321 to $651/night

    Sea La Vie

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool Hot Tub
  126. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  127. $330 to $574/night

    Marmalade Mermaid

    3 BedroomsBathroomsSleeps 8
    3 nights minstay
    Pets OK
  128. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  129. $321 to $498/night

    The Lady Fish

    3 BedroomsBathroomsSleeps 6
    5 nights minstay
  130. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  131. $321 to $498/night

    Sunset Beach

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool Pets OK
  132. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  133. $321 to $574/night

    Dolphin Resort

    3 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
  134. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  135. $161 to $187/night

    Minnow 1

    1 Bedroom BathroomSleeps 2
    3 nights minstay
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  137. $153 to $348/night

    Beach Breeze Hideaway

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pets OK
  138. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  139. $330 to $574/night

    Sunkissed

    3 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
  140. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  141. $421 to $612/night

    Dock of the Bay

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool Pets OK
  142. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  143. $321 to $535/night

    Lazy Pelican

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
  144. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  145. $146 to $187/night

    Seahorse Suite

    Studio BathroomSleeps 2
    3 nights minstay
    Pets OK
  146. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  147. $459 to $841/night

    Fanta Sea

    4 BedroomsBathroomsSleeps 8
    7 nights minstay
    Pool
  148. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  149. $360 to $765/night

    Aqua Vista

    4 BedroomsBathroomsSleeps 8
    7 nights minstay
    Pool
  150. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  151. $130 to $255/night

    Serenity on Sutton

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  152. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  153. $152 to $332/night

    Buttonwood Bliss

    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. $255 to $662/night

    Siesta Key Sanctuary

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Pets OK
    FREE CANCELLATION
  156. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  157. $216 to $459/night

    Pura Vida

    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. $152 to $270/night

    Beach Terrace on Siesta

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  160. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  161. $153 to $265/night

    Surf and Turf at Cedars East

    2 Bedrooms2.5 BathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  162. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  163. $153 to $528/night

    Las Hermanas 1

    Studio BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  164. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  165. $191 to $690/night

    Las Hermanas 2

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    FREE CANCELLATION
  166. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  167. $167 to $366/night

    Siesta Sea Gem

    2 Bedrooms BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
  168. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  169. $375 to $765/night

    Coccoloba

    3 BedroomsBathroomsSleeps 6
    4 nights minstay
    Pool
  170. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  171. $230 to $299/night

    West Bay Point Moorings 214

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
  172. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  173. $230 to $458/night

    Island Haven

    2 BedroomsBathroomsSleeps 4
    28 nights minstay
    Pool
  174. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations
  175. $214 to $268/night

    West Bay Cove 206

    2 BedroomsBathroomsSleeps 4
    28 nights minstay
    Pool
  176. MEMBERS SAVE MORE! Become a member for free today and save on ALL reservations