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Siesta Key Beach Rentals & Vacation Rentals with Swimming Pool - 259 Rentals Available.

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259 Vacation rentals

Filters applied: Swimming pool

1 / 39

Siesta Key House

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

Responds fast! Avg. 1 hour 33 minutes

$380.00

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from $380.00 / night

1 / 38

Siesta Key House

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

Responds fast! Avg. 1 hour 33 minutes

$380.00

Book

from $380.00 / night

1 / 35

Siesta Key House

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

Responds fast! Avg. 1 hour 33 minutes

$380.00

Book

from $380.00 / night

1 / 43

Siesta Key House

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

Responds fast! Avg. 1 hour 33 minutes

$310.00

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from $310.00 / night

1 / 17

Siesta Key House

  • 3
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 37 minutes

$240.00

Book

from $240.00 / night

1 / 33

Siesta Key House

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

Responds fast! Avg. 1 hour 33 minutes

$380.00

Book

from $380.00 / night

1 / 40

Siesta Key House

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

Responds fast! Avg. 1 hour 33 minutes

$380.00

Book

from $380.00 / night

1 / 10

Siesta Key House

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 33 minutes

$255.00

Book

from $255.00 / night

1 / 24

Siesta Key House

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

Responds fast! Avg. 1 hour 33 minutes

$170.00

Book

from $170.00 / night

1 / 16

Siesta Key House

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 33 minutes

$240.00

Book

from $240.00 / night

(34)

1 / 24

Siesta Key Condo

  • 2
  • 4
  • 7 nights min
  • Nearest beach 0.25 mi
  • Swimming pool
  • Child friendly
“Excellent property with lot of parking, laundy on site and warm water in the pool, which was really appreciated on the cooler dates, speacially by the kids. Close walk to a white sandy beach was on asset. Condo was very spacious and full equipped. We...”
- Review left on 01/02/2013

$85.00

Excellent (34 reviews)

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from $85.00 / night

1 / 31

Siesta Key House

  • 4
  • 14
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 33 minutes

$380.00

Book

from $380.00 / night

1 / 43

Siesta Key House

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

Responds fast! Avg. 1 hour 33 minutes

$380.00

Book

from $380.00 / night

1 / 26

Siesta Key House

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

Responds fast! Avg. 1 hour 33 minutes

$170.00

Book

from $170.00 / night

1 / 51

Siesta Key House

  • 8
  • 24
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 33 minutes

$713.00

Book

from $713.00 / night

1 / 40

Siesta Key House

  • 8
  • 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 33 minutes

$713.00

Book

from $713.00 / night

1 / 36

Siesta Key House

  • 8
  • 24
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 33 minutes

$713.00

Book

from $713.00 / night

1 / 29

Siesta Key House

  • 2
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 33 minutes

$200.00

Book

from $200.00 / night

1 / 16

Siesta Key House

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 33 minutes

$310.00

Book

from $310.00 / night

(1)

1 / 25

Siesta Key House

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

Responds fast! Avg. 1 hour 33 minutes

$380.00

Excellent (1 reviews)

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from $380.00 / night

1 / 39

Siesta Key House

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

Responds fast! Avg. 1 hour 33 minutes

$175.00

Book

from $175.00 / night

(3)

1 / 41

Siesta Key Condo

  • 2
  • 4
  • min stay varies
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child friendly

$143.00

Excellent (3 reviews)

Inquire

from $143.00 / night

(6)

1 / 20

Siesta Key House

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

Responds fast! Avg. 1 hour 33 minutes

“The villa was very nice , well equipped, immaculate and very comfortable. We enjoyed the courtyard and pool very much and are stay was very relaxing. The area has everything you would want on vacation along with one of the best beaches. Dave from...”
- Review left on 04/28/2015

$170.00

Excellent (6 reviews)

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from $170.00 / night

1 / 24

Siesta Key House

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 33 minutes

$205.00

Book

from $205.00 / night

1 / 24

Siesta Key Condo

  • 2
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.01 mi
  • Swimming pool
“We recently spent a week in Siesta Key, our fourth year in a row making this our Fall vacation spot. This year, we we fortunate to find an available week at Sandy' Siesta that matched out travel plans. What a great spot! A short walk to the...”
- Review left on 12/16/2016

$125.00

Inquire

from $125.00 / night

(1)

1 / 22

Siesta Key House

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

Responds fast! Avg. 1 hour 33 minutes

$170.00

Very Good (1 reviews)

Book

from $170.00 / night

1 / 29

Siesta Key House

  • 4
  • 13
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 33 minutes

$270.00

Book

from $270.00 / night

1 / 38

Siesta Key House

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

Responds fast! Avg. 1 hour 33 minutes

$235.00

Book

from $235.00 / night

1 / 29

Siesta Key House

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

Responds fast! Avg. 1 hour 33 minutes

$170.00

Book

from $170.00 / night

(1)

1 / 25

Siesta Key Cottage

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

Responds fast! Avg. 1 hour 33 minutes

$153.00

Excellent (1 reviews)

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from $153.00 / night

1 / 24

Siesta Key Cottage

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

Responds fast! Avg. 1 hour 33 minutes

$170.00

Book

from $170.00 / night

(5)

1 / 24

Siesta Key Condo

  • 2
  • 4
  • 7 nights min
  • Nearest beach 0.25 mi
  • Swimming pool
  • Child friendly
“Had an excellent time! Unit was clean and precisely as described. Great location on Siesta Key with a short walk for Groceries, Food and Libations. Beach was a 5min walk across the street (using the signaled crosswalk) through the beachside section...”
- Review left on 03/13/2017

$85.00

Excellent (5 reviews)

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from $85.00 / night

1 / 33

Siesta Key Condo

  • 1
  • 4
  • min stay varies
  • Nearest beach 0.09 mi
  • Swimming pool
  • Ask about children

$199.00

Book

from $199.00 / night

1 / 14

Siesta Key Condo

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

Responds fast! Avg. 3 hours 56 minutes

$100.00

Book

from $100.00 / night

(7)

1 / 38

Siesta Key House

  • 5
  • 13
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$450.00

Excellent (7 reviews)

Book

from $450.00 / night

1 / 24

Siesta Key House

  • 3
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 33 minutes

$240.00

Book

from $240.00 / night

1 / 25

Siesta Key House

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

Responds fast! Avg. 1 hour 33 minutes

$170.00

Book

from $170.00 / night

1 / 27

Siesta Key House

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

Responds fast! Avg. 1 hour 33 minutes

$170.00

Book

from $170.00 / night

(2)

1 / 18

Siesta Key Cottage

  • 4
  • 11
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 33 minutes

“We loved the home. We had our whole family, parents, children, grandchildren, and it was spacious enough for everyone to have their own space. The tropical back yard was gorgeous. The kitchen was very well equipped. The only negative is the...”
- Review left on 10/24/2016

$310.00

Very Good (2 reviews)

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from $310.00 / night

1 / 66

Siesta Key House

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

Responds fast! Avg. 1 hour 33 minutes

$713.00

Book

from $713.00 / night