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Siesta Key Waterfront Beach Rentals, Vacation Rentals & More - 375 Rentals Available.

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375 Vacation rentals

Filters applied: Waterfront

1 / 43

Siesta Key House

  • 4
  • 12
  • Min stay varies
  • Child friendly
  • Pet friendly

$380.00

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from $380.00 / night

1 / 39

Siesta Key House

  • 4
  • 12
  • Min stay varies
  • Child friendly
  • Pet friendly

$345.00

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from $345.00 / night

1 / 33

Siesta Key House

  • 4
  • 12
  • 4 nights min
  • Child friendly
  • Pet friendly

$380.00

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from $380.00 / night

(1)

1 / 24

Siesta Key Condo

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

$201.00

Excellent (1 reviews)

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from $201.00 / night

1 / 38

Siesta Key House

  • 4
  • 12
  • 4 nights min
  • Child friendly

$380.00

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from $380.00 / night

1 / 35

Siesta Key House

  • 4
  • 12
  • Min stay varies
  • Child friendly
  • Pet friendly

$380.00

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from $380.00 / night

1 / 24

Siesta Key House

  • 4
  • 6
  • Min stay varies
  • Child friendly
  • Pet friendly

$170.00

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from $170.00 / night

1 / 17

Siesta Key House

  • 3
  • 10
  • Min stay varies
  • Child friendly
  • Pet friendly

$240.00

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from $240.00 / night

1 / 31

Siesta Key House

  • 4
  • 14
  • Min stay varies
  • Child friendly

$380.00

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from $380.00 / night

(1)

1 / 24

Siesta Key Condo

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

$180.00

Excellent (1 reviews)

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from $180.00 / night

1 / 27

Siesta Key House

  • 4
  • 8
  • Min stay varies
  • Child friendly

$150.00

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from $150.00 / night

1 / 10

Siesta Key House

  • 4
  • 10
  • Min stay varies
  • Child friendly

$256.00

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from $256.00 / night

1 / 34

Siesta Key Townhouse

  • 3
  • 8
  • Min stay varies
  • Child friendly

$240.00

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from $240.00 / night

(3)

1 / 34

Siesta Key House

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool

$201.00

Excellent (3 reviews)

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from $201.00 / night

1 / 16

Siesta Key House

  • 3
  • 8
  • Min stay varies
  • Child friendly
  • Pet friendly

$240.00

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from $240.00 / night

1 / 24

Siesta Key Condo

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

$229.00

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from $229.00 / night

1 / 24

Siesta Key Condo

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

$140.00

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from $140.00 / night

(1)

1 / 25

Siesta Key House

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

$326.00

Excellent (1 reviews)

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from $326.00 / night

1 / 23

Siesta Key House

  • 1
  • 4
  • Min stay varies
  • Child friendly

$101.00

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from $101.00 / night

1 / 24

Siesta Key Condo

  • 2
  • 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$180.00

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from $180.00 / night

(6)

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 (6 reviews)

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from $125.00 / night

(5)

1 / 21

Siesta Key House

  • 4
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“We really enjoyed our stay and would come back . The only reason I gave four stars is we had six people and the sleeper sofa was so bad that they slept on the floor. The rental was well equipped for cooking in and beach stuff( cart to haul chairs,...”
- Review left on 08/07/2016

$266.00

Very Good (5 reviews)

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from $266.00 / night

1 / 24

Siesta Key Condo

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

$158.00

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from $158.00 / night

1 / 36

Siesta Key House

  • 8
  • 24
  • 4 nights min
  • Child friendly
  • Pet friendly

$712.00

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from $712.00 / night

1 / 40

Siesta Key House

  • 8
  • 12
  • 4 nights min
  • Child friendly
  • Pet friendly

$712.00

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from $712.00 / night

(2)

1 / 24

Siesta Key House

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

$140.00

Very Good (2 reviews)

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from $140.00 / night

1 / 22

Siesta Key House

  • 2
  • 4
  • 4 nights min
  • Child friendly
  • Pet friendly

$170.00

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from $170.00 / night

(1)

1 / 24

Siesta Key Condo

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

$229.00

Excellent (1 reviews)

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from $229.00 / 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

$173.00

Excellent (25 reviews)

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from $173.00 / night

1 / 24

Siesta Key Cottage

  • 2
  • 6
  • 4 nights min
  • Child friendly

$170.00

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from $170.00 / night

1 / 24

Siesta Key House

  • 3
  • 10
  • Min stay varies
  • Child friendly
  • Pet friendly

$240.00

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from $240.00 / night

1 / 40

Siesta Key House

  • 6
  • 16
  • Min stay varies
  • Child friendly

$415.00

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from $415.00 / 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

(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 / 24

Siesta Key Villa

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

$215.00

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from $215.00 / night

1 / 24

Siesta Key Condo

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

$180.00

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from $180.00 / night

(1)

1 / 47

Siesta Key House

  • 4
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$235.00

Excellent (1 reviews)

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from $235.00 / night

1 / 24

Siesta Key Condo

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

$215.00

Inquire

from $215.00 / night

1 / 24

Siesta Key House

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

$250.00

Inquire

from $250.00 / night

1 / 45

Siesta Key House

  • 4
  • 10
  • Min stay varies
  • Child friendly
  • Pet friendly

$175.00

Book

from $175.00 / night