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Siesta Key Beach Rentals & Vacation Rentals with Swimming Pool - 130 Rentals Available.

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130 Vacation rentals

Filters applied: Swimming pool

1 / 24

Siesta Key Condo

  • 2
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $129 / night

1 / 24

Siesta Key Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $180 / night

1 / 24

Siesta Key Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $186 / night

1 / 24

Siesta Key Villa

  • 3
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $200 / night

1 / 24

Siesta Key Condo

  • 1
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $195 / night

(6)

1 / 37

Siesta Key House

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$400

Excellent (6 reviews)

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from $400 / night

1 / 24

Siesta Key Condo

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

from $150 / night

(25)

1 / 24

Siesta Key Condo

  • 2
  • 6
  • 7 nights min
  • Nearest beach 0.08 mi
  • Swimming pool
  • Child friendly

$126

Excellent (25 reviews)

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from $126 / night

1 / 24

Siesta Key Condo

  • 2
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $229 / night

(1)

1 / 25

Siesta Key House

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$326

Excellent (1 reviews)

Inquire

from $326 / night

1 / 34

Siesta Key House

  • 4
  • 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $214 / night

1 / 29

Siesta Key House

  • 5
  • 13
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$525

Book

from $525 / night

1 / 24

Siesta Key Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $180 / night

1 / 24

Siesta Key House

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $200 / night

(6)

1 / 20

Siesta Key House

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$146

Excellent (6 reviews)

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from $146 / night

(1)

1 / 24

Siesta Key Condo

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$315

Excellent (1 reviews)

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from $315 / night

1 / 36

Siesta Key Condo

  • 4
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $400 / night

(3)

1 / 18

Siesta Key Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$230

Excellent (3 reviews)

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from $230 / night

(2)

1 / 18

Siesta Key Cottage

  • 4
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$286

Very Good (2 reviews)

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from $286 / night

1 / 24

Siesta Key Condo

  • 1
  • 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

from $160 / night

(2)

1 / 19

Siesta Key House

  • 5
  • 12
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$250

Excellent (2 reviews)

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from $250 / night

(5)

1 / 21

Siesta Key Condo

  • 1
  • 3
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$195

Excellent (5 reviews)

Inquire

from $195 / night

1 / 29

Siesta Key House

  • 4
  • 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $310 / night

1 / 20

Siesta Key Villa

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

from $285 / night

(5)

1 / 24

Siesta Key Condo

  • 2
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.01 mi
  • Swimming pool

$122

Excellent (5 reviews)

Inquire

from $122 / night

1 / 24

Siesta Key Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $243 / night

1 / 35

Siesta Key House

  • 4
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $179 / night

(33)

1 / 24

Siesta Key Condo

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$75

Excellent (33 reviews)

Book

from $75 / night

1 / 31

Siesta Key House

  • 4
  • 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $300 / night

(7)

1 / 23

Siesta Key Condo

  • 2
  • 6
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$135

Very Good (7 reviews)

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from $135 / night

1 / 26

Siesta Key House

  • 4
  • 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $266 / night

(3)

1 / 11

Siesta Key Villa

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$144

Excellent (3 reviews)

Inquire

from $144 / night

(1)

1 / 24

Siesta Key Condo

  • 1
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$200

Very Good (1 reviews)

Inquire

from $200 / night

1 / 24

Siesta Key Condo

  • 2
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $215 / night

1 / 24

Siesta Key Condo

  • 2
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $180 / night

(2)

1 / 24

Siesta Key Condo

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$195

Average (2 reviews)

Inquire

from $195 / night

(5)

1 / 21

Siesta Key House

  • 4
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$266

Very Good (5 reviews)

Inquire

from $266 / night

1 / 24

Siesta Key House

  • 4
  • 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $214 / night

(2)

1 / 34

Siesta Key House

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$179

Excellent (2 reviews)

Inquire

from $179 / night

(1)

1 / 28

Siesta Key House

  • 2
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$179

Excellent (1 reviews)

Inquire

from $179 / night