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  1. $345 to $688/night

    Canario Cottage

    3 BedroomsBathroomsSleeps 6
    3 nights minstay
    Pool
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  3. $251 to $407/night

    Crystal Sands on Siesta

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
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  5. $183 to $336/night

    Imperial Sunsets on Siesta

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  7. $91 to $158/night

    Beneva Brooke Beauty

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  9. $207 to $387/night

    Hawk's Sea Nest

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
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  11. $153 to $332/night

    It's a Shore Thing

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  13. $169 to $281/night

    Salty Soldi

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  15. $216 to $459/night

    Beach Haven

    2 BedroomsBathroomsSleeps 8
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  17. $136 to $306/night

    Siesta Bayside Bliss

    1 BedroomBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  19. $465 to $930/night

    Captivated by the Sea

    2 BedroomsBathroomsSleeps 8
    1 night minstay
    Pool
    FREE CANCELLATION
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  21. $214 to $383/night

    The Villas 2B

    2 Bedrooms BathroomSleeps 4
    7 nights minstay
    Pool
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  23. $146 to $268/night

    The Villas 2A

    1 Bedroom BathroomSleeps 4
    1 night minstay
    Pool
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  25. $459 to $765/night

    The Salted Coconut

    3 BedroomsBathroomsSleeps 8
    4 nights minstay
    Pool
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  27. $214 to $383/night

    Coquina Cottage B

    2 BedroomsBathroomsSleeps 4
    3 nights minstay
    Pool
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  29. $214 to $383/night

    Hidden Pearl

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
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  31. $192 to $268/night

    Sunbow Bay 108

    2 BedroomsBathroomsSleeps 4
    28 nights minstay
    Pool
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  33. $204 to $285/night

    Sandy Cove Oasis

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  35. $295 to $642/night

    Crescent Siesta Key Charmer

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  37. $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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  39. $134 to $291/night

    Beach Way Getaway

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool
    FREE CANCELLATION
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  41. $183 to $281/night

    Sea Winds on Siesta

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  43. $282 to $611/night

    The Windward House

    3 Bedrooms2.5 BathroomsSleeps 6
    2 nights minstay
    Pool Pets OK
    FREE CANCELLATION
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  45. $216 to $459/night

    Just Beachy

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  47. $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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  49. $330 to $574/night

    Sapphire Beach House

    3 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Pets OK
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  51. $214 to $383/night

    Sea Pirate 5

    2 Bedrooms BathroomSleeps 4
    7 nights minstay
    Pool
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  53. $214 to $383/night

    The Getaway

    2 BedroomsBathroomsSleeps 6
    7 nights minstay
    Pool
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  55. $130 to $255/night

    Serenity on Sutton

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  57. $152 to $332/night

    Buttonwood Bliss

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  59. $255 to $662/night

    Siesta Key Sanctuary

    3 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Pets OK
    FREE CANCELLATION
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  61. $216 to $459/night

    Pura Vida

    2 BedroomsBathroomsSleeps 6
    2 nights minstay
    Pool Hot Tub
    FREE CANCELLATION
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  63. $152 to $270/night

    Beach Terrace on Siesta

    1 Bedroom BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  65. $167 to $366/night

    Siesta Sea Gem

    2 Bedrooms BathroomSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  67. $624 to $1,040/night

    Magnificent Gulf View Condo in Shipp's Landing

    2 BedroomsBathroomsSleeps 6
    1 night minstay
    Pool Hot Tub
    FREE CANCELLATION
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  69. $153 to $265/night

    Surf and Turf at Cedars East

    2 Bedrooms2.5 BathroomsSleeps 4
    2 nights minstay
    Pool
    FREE CANCELLATION
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  71. $214 to $268/night

    West Bay Cove 206

    2 BedroomsBathroomsSleeps 4
    28 nights minstay
    Pool
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  73. $230 to $299/night

    West Bay Point Moorings 214

    2 BedroomsBathroomsSleeps 4
    2 nights minstay
    Pool Hot Tub
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