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Siesta Key 2-bedroom Beach Rentals, Vacation Rentals & More - 125 Rentals Available.

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125 Vacation rentals

Filters applied: 2+ Bedrooms

(41)

1 / 24

Siesta Key Condo

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.25 mi
  • Swimming pool
“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

$136.00

Very Good (41 reviews)

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from $136.00 / night

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(29)

1 / 24

Siesta Key Condo

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
“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

$221.00

Excellent (29 reviews)

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from $221.00 / night

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(7)

1 / 24

Siesta Key Condo

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.25 mi
  • Swimming pool
“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

$136.00

Excellent (7 reviews)

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from $136.00 / night

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(16)

1 / 24

Siesta Key House

  • 5
  • 13
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

$974.00

Very Good (16 reviews)

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from $974.00 / night

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(2)

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

$300.00

Excellent (2 reviews)

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from $300.00 / night

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(15)

1 / 41

Siesta Key Condo

  • 2
  • 4
  • 3 nights min
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child friendly

$199.00

Excellent (15 reviews)

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from $199.00 / night

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(24)

1 / 31

Siesta Key Condo

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“My wife and I spent 2 weeks at this well kept and wonderfully located condominium. We loved that it is a garden style complex and not a high rise building. This unit being on the 1st floor makes it even better. Being able to walk right out to the...”
- Review left on 02/05/2021

$258.00

Excellent (24 reviews)

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from $258.00 / night

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(2)

1 / 22

Siesta Key House

  • 3
  • 7
  • 14 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“My husband and I stayed at Tiffany Sands for the months of February and March 2016. We loved the proximity to the beach and Siesta Key Village. The townhouse is well appointed and had nearly everything we needed for a comfortable 2 month stay. The...”
- Review left on 04/28/2016

$401.00

Very Good (2 reviews)

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from $401.00 / night

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(1)

1 / 23

Siesta Key Condo

  • 3
  • 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$491.00

Excellent (1 reviews)

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from $491.00 / night

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1 / 27

Siesta Key Apartment

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$264.00

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from $264.00 / night

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1 / 26

Siesta Key Apartment

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$290.00

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from $290.00 / night

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(1)

1 / 26

Siesta Key Apartment

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$142.00

Excellent (1 reviews)

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from $142.00 / night

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(1)

1 / 37

Siesta Key Apartment

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$290.00

Very Good (1 reviews)

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from $290.00 / night

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1 / 22

Siesta Key Apartment

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$249.00

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from $249.00 / night

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1 / 15

Siesta Key Apartment

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$137.00

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from $137.00 / night

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1 / 23

Siesta Key Apartment

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$171.00

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from $171.00 / night

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1 / 38

Siesta Key Apartment

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$167.00

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from $167.00 / night

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1 / 32

Siesta Key Apartment

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$171.00

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from $171.00 / night

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1 / 20

Siesta Key Apartment

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$249.00

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from $249.00 / night

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1 / 23

Siesta Key Apartment

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$264.00

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from $264.00 / night

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1 / 21

Siesta Key Apartment

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$142.00

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from $142.00 / night

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1 / 35

Siesta Key Apartment

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$264.00

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from $264.00 / night

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1 / 19

Siesta Key Apartment

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$142.00

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from $142.00 / night

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1 / 26

Siesta Key Apartment

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$167.00

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from $167.00 / night

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1 / 33

Siesta Key Apartment

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$264.00

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from $264.00 / night

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1 / 31

Siesta Key Apartment

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$290.00

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from $290.00 / night

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1 / 30

Siesta Key Apartment

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$137.00

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from $137.00 / night

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1 / 28

Siesta Key Apartment

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$142.00

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from $142.00 / night

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1 / 28

Siesta Key Apartment

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$142.00

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from $142.00 / night

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1 / 29

Siesta Key Apartment

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$296.00

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from $296.00 / night

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1 / 25

Siesta Key Apartment

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$171.00

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from $171.00 / night

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1 / 20

Siesta Key Apartment

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$237.00

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from $237.00 / night

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1 / 26

Siesta Key Apartment

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$290.00

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from $290.00 / night

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1 / 15

Siesta Key Apartment

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$264.00

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from $264.00 / night

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1 / 24

Siesta Key Apartment

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$249.00

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from $249.00 / night

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1 / 36

Siesta Key Apartment

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$264.00

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from $264.00 / night

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1 / 29

Siesta Key Apartment

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$264.00

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from $264.00 / night

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1 / 31

Siesta Key Apartment

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$142.00

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from $142.00 / night

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(1)

1 / 16

Siesta Key Apartment

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$142.00

Excellent (1 reviews)

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from $142.00 / night

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1 / 47

Siesta Key Apartment

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$451.00

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from $451.00 / night

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