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Siesta Key Waterfront Beach Rentals, Vacation Rentals & More - 332 Rentals Available.

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332 Vacation rentals

Filters applied: Waterfront

(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

(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

(1)

1 / 39

Siesta Key House

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

Responds fast! Avg. 1 hour 48 minutes

$380.00

Excellent (1 reviews)

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from $380.00 / night

(13)

1 / 17

Siesta Key Condo

  • 1
  • 4
  • 7 nights min
  • 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

$120.00

Very Good (13 reviews)

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from $120.00 / 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

(4)

1 / 33

Siesta Key House

  • 3
  • 9
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly

$395.00

Excellent (4 reviews)

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from $395.00 / night

(1)

1 / 24

Siesta Key Apartment

  • 3
  • 8
  • min stay varies
  • Child friendly

$495.00

Excellent (1 reviews)

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from $495.00 / night

1 / 36

Siesta Key House

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

Responds fast! Avg. 1 hour 48 minutes

$713.00

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from $713.00 / 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
  • 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

(7)

1 / 15

Siesta Key House

  • 4
  • 14
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“We used this house as a work retreat and a celebration! Overall, the house was perfect. Plenty of space, the views were awesome, the living room was great for a work meeting (5 people). The balconies were great. A good location...away from the town...”
- Review left on 01/23/2017

$500.00

Excellent (7 reviews)

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from $500.00 / 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 / 28

Siesta Key Apartment

  • 2
  • 8
  • min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning

$495.00

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from $495.00 / 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

$380.00

Excellent (1 reviews)

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from $380.00 / 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 / 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

(12)

1 / 40

Siesta Key Condo

  • 2
  • 6
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Great place! Everything was wonderful,beach was a short walk away. Love all the new addition to public beach. Pool was heated,we went swimming every day. Unit was very clean and comfortable,couldn't ask for a better place. Took the free taxi to...”
- Review left on 01/06/2017

$89.00

Excellent (12 reviews)

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from $89.00 / night

1 / 45

Siesta Key House

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

Responds fast! Avg. 1 hour 48 minutes

$175.00

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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)

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from $143.00 / night

(6)

1 / 23

Siesta Key Condo

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

$236.00

Excellent (6 reviews)

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from $236.00 / night

(2)

1 / 23

Siesta Key House

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

$550.00

Excellent (2 reviews)

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from $550.00 / night

(1)

1 / 25

Siesta Key Cottage

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

Responds fast! Avg. 1 hour 48 minutes

$153.00

Excellent (1 reviews)

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from $153.00 / night

(9)

1 / 37

Siesta Key House

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
“House was newly renovated, nicely funnies and clean. Short walk to Siesta Key Beach and 1 mile to town. Very sweet neighborhood...”
- Review left on 03/05/2017

$395.00

Excellent (9 reviews)

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from $395.00 / night

1 / 10

Siesta Key House

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

Responds fast! Avg. 1 hour 48 minutes

$255.00

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from $255.00 / night

(6)

1 / 21

Siesta Key Condo

  • 1
  • 3
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“We actually stayed in unit #113 and it was simple but clean with updated kitchen. The grounds, pool, and amenities were well maintained and clean. The Gulf view was amazing! We have visited many beaches but this was the most beautiful with a quiet...”
- Review left on 07/07/2016

$200.00

Excellent (6 reviews)

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from $200.00 / 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 / 38

Siesta Key House

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

Responds fast! Avg. 1 hour 48 minutes

$235.00

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from $235.00 / night

(1)

1 / 26

Siesta Key House

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

Responds fast! Avg. 1 hour 48 minutes

$310.00

Excellent (1 reviews)

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from $310.00 / night

1 / 26

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

1 / 14

Siesta Key Apartment

  • 1
  • 4
  • min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning

$200.00

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from $200.00 / night

1 / 30

Siesta Key House

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

Responds fast! Avg. 1 hour 48 minutes

$170.00

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from $170.00 / 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 / 36

Siesta Key House

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

Responds fast! Avg. 1 hour 48 minutes

$380.00

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from $380.00 / night

1 / 29

Siesta Key House

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

Responds fast! Avg. 1 hour 48 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 48 minutes

$170.00

Book

from $170.00 / night

1 / 40

Siesta Key House

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

Responds fast! Avg. 1 hour 48 minutes

$380.00

Book

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 48 minutes

$175.00

Book

from $175.00 / night

1 / 40

Siesta Key House

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

Responds fast! Avg. 1 hour 48 minutes

$235.00

Book

from $235.00 / night