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Siesta Key Beach Rentals & Vacation Rentals with Swimming Pool - 260 Rentals Available.

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260 Vacation rentals

Filters applied: Swimming pool

(36)

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 (36 reviews)

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from $85.00 / 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

(26)

1 / 24

Siesta Key Condo

  • 2
  • 6
  • 7 nights min
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child friendly
“This was our first trip to Siesta Key, but not our last! We are already booking another stay at Siesta Breakers for next year. It is a great location on the Beach and great access to the mainland...”
- Review left on 07/14/2014

$147.00

Excellent (26 reviews)

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from $147.00 / night

(7)

1 / 38

Siesta Key House

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

$450.00

Excellent (7 reviews)

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from $450.00 / night

(9)

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

Excellent (9 reviews)

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from $125.00 / night

1 / 24

Siesta Key House

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

Responds fast! Avg. 2 hours 20 minutes

$240.00

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from $240.00 / night

(1)

1 / 23

Siesta Key House

  • 4
  • 12
  • min stay varies
  • Nearest beach 0.2 mi
  • Swimming pool
  • Child friendly

$550.00

Excellent (1 reviews)

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from $550.00 / night

1 / 17

Siesta Key House

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

Responds fast! Avg. 1 hour 48 minutes

$240.00

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from $240.00 / night

(1)

1 / 22

Siesta Key House

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

Responds fast! Avg. 1 hour 48 minutes

$170.00

Very Good (1 reviews)

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from $170.00 / night

(1)

1 / 39

Siesta Key House

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

Responds fast! Avg. 1 hour 48 minutes

$381.00

Excellent (1 reviews)

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from $381.00 / night

(6)

1 / 22

Siesta Key Condo

  • 1
  • 4
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 1 hour 59 minutes

“We stayed for a week and had the best time ever. The accommodations are top notch, locals are very friendly, food delicious and breathtaking beaches. Definitely looking forward to coming back”
- Review left on 12/15/2015

$127.00

Excellent (6 reviews)

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from $127.00 / night

1 / 33

Siesta Key Condo

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

$199.00

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from $199.00 / night

1 / 26

Siesta Key House

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

Responds fast! Avg. 2 hours 20 minutes

$170.00

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from $170.00 / night

1 / 36

Siesta Key House

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

Responds fast! Avg. 1 hour 48 minutes

$381.00

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from $381.00 / night

1 / 45

Siesta Key House

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

Responds fast! Avg. 2 hours 20 minutes

$175.00

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from $175.00 / night

(1)

1 / 25

Siesta Key Cottage

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

Responds fast! Avg. 2 hours 20 minutes

$153.00

Excellent (1 reviews)

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from $153.00 / night

(1)

1 / 25

Siesta Key House

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

Responds fast! Avg. 1 hour 48 minutes

$381.00

Excellent (1 reviews)

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from $381.00 / night

1 / 29

Siesta Key House

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

Responds fast! Avg. 2 hours 20 minutes

$170.00

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from $170.00 / night

1 / 33

Siesta Key House

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

Responds fast! Avg. 1 hour 48 minutes

$381.00

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from $381.00 / night

1 / 38

Siesta Key House

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

Responds fast! Avg. 2 hours 20 minutes

$235.00

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from $235.00 / night

(6)

1 / 20

Siesta Key House

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

Responds fast! Avg. 2 hours 20 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

(9)

1 / 18

Siesta Key Condo

  • 2
  • 4
  • min stay varies
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child friendly
“Great property, beautiful pool, super close to the beach and the village - will totally be back! Awesome property management as well...”
- Review left on 06/13/2016

$143.00

Excellent (9 reviews)

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from $143.00 / night

1 / 14

Siesta Key Condo

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

Responds fast! Avg. 3 hours 56 minutes

$99.00

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from $99.00 / night

1 / 27

Siesta Key House

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 20 minutes

$150.00

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from $150.00 / night

1 / 27

Siesta Key House

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

Responds fast! Avg. 1 hour 48 minutes

$170.00

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from $170.00 / night

(5)

1 / 24

Siesta Key Condo

  • 1
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“Thank you for a wonderful week! The room was beautiful and Mary Ann and staff were all so accommodating to anything that you may need! We would highly recommend Siesta Palms to everyone! We are looking forward to coming back as soon as possible,...”
- Review left on 07/13/2016

$199.00

Excellent (5 reviews)

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from $199.00 / night

1 / 31

Siesta Key House

  • 4
  • 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 48 minutes

$310.00

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from $310.00 / night

1 / 24

Siesta Key House

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

Responds fast! Avg. 1 hour 17 minutes

$205.00

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from $205.00 / night

1 / 35

Siesta Key House

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

Responds fast! Avg. 1 hour 48 minutes

$381.00

Book

from $381.00 / night

1 / 43

Siesta Key House

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

Responds fast! Avg. 1 hour 48 minutes

$381.00

Book

from $381.00 / night

1 / 31

Siesta Key House

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

Responds fast! Avg. 2 hours 20 minutes

$381.00

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from $381.00 / 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)

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from $143.00 / night

1 / 39

Siesta Key House

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

Responds fast! Avg. 2 hours 20 minutes

$175.00

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from $175.00 / night

1 / 24

Siesta Key Cottage

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

Responds fast! Avg. 1 hour 48 minutes

$170.00

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from $170.00 / night

1 / 24

Siesta Key House

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

Responds fast! Avg. 1 hour 48 minutes

$170.00

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from $170.00 / night

(4)

1 / 25

Siesta Key Condo

  • 1
  • 4
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning
“This place is absolutely great. Me and my girlfriend spent two nights over the weekend at this condo. First of all this place has more stuff that we could imagine. It literally includes everything you need for having a pleasant and comfortable stay....”
- Review left on 07/26/2016

$90.00

Very Good (4 reviews)

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from $90.00 / night

1 / 40

Siesta Key House

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

Responds fast! Avg. 2 hours 20 minutes

$381.00

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from $381.00 / night

1 / 34

Siesta Key Townhouse

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

Responds fast! Avg. 1 hour 48 minutes

$240.00

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from $240.00 / night

1 / 66

Siesta Key House

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

Responds fast! Avg. 1 hour 48 minutes

$714.00

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from $714.00 / night

(1)

1 / 26

Siesta Key House

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

Responds fast! Avg. 2 hours 20 minutes

$310.00

Excellent (1 reviews)

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from $310.00 / night