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Siesta Key Waterfront Beach Rentals, Vacation Rentals & More - 351 Rentals Available.

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351 Vacation rentals

Filters applied: Waterfront

(12)

1 / 16

Siesta Key Condo

  • 1
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“We stayed in Crescent Royale #409. Condo was extremely clean and well supplied. We had flown in and was thrillled to see beach chairs, umbrellas, towels and etc. that we couldn't bring along. The property was peaceful and quiet. Only problem was RED...”
- Review left on 10/04/2016

$144.00

Very Good (12 reviews)

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from $144.00 / night

1 / 38

Siesta Key House

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

$380.00

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from $380.00 / night

1 / 39

Siesta Key House

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

$380.00

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from $380.00 / night

1 / 17

Siesta Key House

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

$240.00

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from $240.00 / night

1 / 43

Siesta Key House

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

$310.00

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from $310.00 / 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

$101.00

Excellent (5 reviews)

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from $101.00 / night

(1)

1 / 22

Siesta Key House

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

$170.00

Very Good (1 reviews)

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from $170.00 / night

(33)

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

$101.00

Excellent (33 reviews)

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from $101.00 / night

1 / 40

Siesta Key House

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

$380.00

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from $380.00 / night

(25)

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 (25 reviews)

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from $147.00 / night

1 / 38

Siesta Key House

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

$235.00

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from $235.00 / night

1 / 26

Siesta Key House

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

$170.00

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from $170.00 / night

(5)

1 / 22

Siesta Key Condo

  • 1
  • 4
  • 3 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
“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

$150.00

Excellent (5 reviews)

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from $150.00 / night

1 / 33

Siesta Key House

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

$380.00

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from $380.00 / night

(1)

1 / 25

Siesta Key House

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

$380.00

Excellent (1 reviews)

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from $380.00 / night

1 / 51

Siesta Key House

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

$713.00

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from $713.00 / night

1 / 24

Siesta Key House

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

$170.00

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from $170.00 / night

1 / 16

Siesta Key House

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

$240.00

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from $240.00 / night

1 / 35

Siesta Key House

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

$380.00

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from $380.00 / night

1 / 31

Siesta Key House

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

$380.00

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from $380.00 / night

1 / 24

Siesta Key House

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

$206.00

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from $206.00 / night

1 / 29

Siesta Key House

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

$270.00

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from $270.00 / night

1 / 45

Siesta Key House

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

$175.00

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from $175.00 / night

(2)

1 / 18

Siesta Key Cottage

  • 4
  • 11
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“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 / 43

Siesta Key House

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

$380.00

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from $380.00 / night

1 / 40

Siesta Key House

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

$713.00

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from $713.00 / night

1 / 66

Siesta Key House

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

$713.00

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from $713.00 / night

1 / 39

Siesta Key House

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

$175.00

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from $175.00 / night

1 / 30

Siesta Key House

  • 2
  • 6
  • Min stay varies
  • Child friendly
  • Pet friendly

$170.00

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from $170.00 / night

1 / 24

Siesta Key Cottage

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

$170.00

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from $170.00 / night

1 / 16

Siesta Key House

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

$310.00

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from $310.00 / night

1 / 27

Siesta Key House

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

$170.00

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from $170.00 / night

1 / 40

Siesta Key House

  • 4
  • 8
  • Min stay varies
  • Child friendly
  • Pet friendly

$235.00

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from $235.00 / night

1 / 27

Siesta Key House

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

$150.00

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from $150.00 / night

(1)

1 / 26

Siesta Key House

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

$310.00

Excellent (1 reviews)

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from $310.00 / night

1 / 34

Siesta Key Townhouse

  • 3
  • 9
  • Min stay varies
  • Child friendly

$240.00

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from $240.00 / night

1 / 29

Siesta Key House

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

$170.00

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from $170.00 / night

(1)

1 / 16

Siesta Key Condo

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“Siesta Key is the best beach I ever been so far and this place that Jack and Darlene provide is a dream. Everything is clean and in perfect working condition. The beach is very nice (and I have visited many being a South Floridian), crystal clear and...”
- Review left on 09/19/2016

$186.00

Excellent (1 reviews)

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from $186.00 / night

(2)

1 / 10

Siesta Key Condo

  • 1
  • 4
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“FIVE STARS!!!!! Terry the owner is a great guy that insured our stay in his condo went well. The condo has a great location just a couple of blocks from the Siesta Key Beach. The condo has everything you need for a great beach experience. The...”
- Review left on 01/24/2017

$81.00

Excellent (2 reviews)

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from $81.00 / night

1 / 36

Siesta Key Condo

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

$500.00

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from $500.00 / night