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Siesta Key 2-bedroom Beach Rentals, Vacation Rentals & More - 231 Rentals Available.

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231 Vacation rentals

Filters applied: 2+ Bedrooms

1 / 41

Siesta Key House

  • 3
  • 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly

$395

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from $395 / night

(6)

1 / 37

Siesta Key House

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

$400

Excellent (6 reviews)

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from $400 / night

(1)

1 / 10

Siesta Key Condo

  • 2
  • 6
  • 7 nights min
  • Ask about children
  • Air conditioning
“My husband and I enjoyed our two week respite from winter at this lovely well equipped condo. The unit was very clean, with great beach access and a pool on the property. A very well stocked grocery store is within walking distance of the complex,...”
- Review left on 01/09/2017

$146

Excellent (1 reviews)

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from $146 / night

1 / 20

Siesta Key Villa

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

from $285 / night

1 / 24

Siesta Key Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $243 / night

(7)

1 / 15

Siesta Key House

  • 4
  • 14
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • 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

$714

Excellent (7 reviews)

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from $714 / night

1 / 26

Siesta Key House

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

from $266 / night

(4)

1 / 11

Siesta Key Condo

  • 2
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning
“We recently stayed at this condo for a few weeks. The condo is in very good shape and is charming. The management staff is amazing and always easy to reach. Very close to the beach and the pool. Overall, we had a pleasant experience...”
- Review left on 08/30/2013

$100

Excellent (4 reviews)

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from $100 / night

(6)

1 / 18

Siesta Key Condo

  • 2
  • 6
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“just got back from a great vacation in siesta key . The condo was clean and the beds were extremely comfortable. The owner also provided all the necessary items needed to go and enjoy the beautiful beach !!!! The condo is located close to the beach...”
- Review left on 05/09/2016

$154

Very Good (6 reviews)

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from $154 / night

(25)

1 / 24

Siesta Key Condo

  • 2
  • 6
  • 7 nights min
  • Nearest beach 0.08 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

$142

Excellent (25 reviews)

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from $142 / night

1 / 24

Siesta Key Condo

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

from $180 / night

1 / 24

Siesta Key Condo

  • 2
  • 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $243 / night

1 / 29

Siesta Key House

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

from $310 / night

(2)

1 / 20

Siesta Key Townhouse

  • 3
  • 10
  • 7 nights min
  • Ask about children
  • Air conditioning
“The home was beautiful and thank God for the functional elevator. It's proximity to the beach and Siesta Key Village was perfect...”
- Review left on 07/18/2016

$200

Very Good (2 reviews)

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from $200 / night

(1)

1 / 34

Siesta Key House

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

$179

Excellent (1 reviews)

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from $179 / night

1 / 24

Siesta Key House

  • 4
  • 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $214 / night

(2)

1 / 19

Siesta Key House

  • 5
  • 12
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Beautiful home with so many added features! We are definitely coming back and staying at The Grand Canal...”
- Review left on 10/20/2015

$250

Excellent (2 reviews)

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from $250 / night

1 / 24

Siesta Key Condo

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

from $229 / night

(8)

1 / 30

Siesta Key Condo

  • 2
  • 4
  • Min stay varies
  • Child friendly
  • Air conditioning
“My husband & I chose this condo on-line. It was immaculate, very nicely renovated, had a wonderful view of the boat docks and pool, and an owner who could not have been nicer. Midnight Cove II community is a gem. People & staff are friendly, the...”
- Review left on 01/30/2017

$119

Excellent (8 reviews)

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from $119 / night

1 / 35

Siesta Key House

  • 4
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $179 / night

(7)

1 / 23

Siesta Key Condo

  • 2
  • 6
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“Unfortunately my wife and I could only stay a few days. The condo is well kept, well equipped. Short 300 yard walk to the beach was awesome. We have stayed many times in Siesta Key and were impressed with our first visit to this condo. Would...”
- Review left on 03/04/2016

$135

Very Good (7 reviews)

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from $135 / night

(1)

1 / 28

Siesta Key House

  • 2
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“My family and I had the best time! We enjoyed the house and the pool so much we didn't even go out. Spent 3 days of bliss. This was a last minute reservation and the management company and the owner were fantastic in dealing with my request. My...”
- Review left on 06/23/2016

$179

Excellent (1 reviews)

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from $179 / 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

Excellent (12 reviews)

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from $89 / night

1 / 24

Siesta Key Condo

  • 2
  • 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $186 / night

1 / 36

Siesta Key Condo

  • 4
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $400 / night

1 / 24

Siesta Key Condo

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

from $150 / night

1 / 24

Siesta Key Condo

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

from $180 / night

1 / 24

Siesta Key Condo

  • 2
  • 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $243 / night

1 / 24

Siesta Key Condo

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

from $129 / night

1 / 31

Siesta Key House

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

from $300 / night

(2)

1 / 18

Siesta Key Cottage

  • 4
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • 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

$286

Very Good (2 reviews)

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from $286 / night

(2)

1 / 18

Siesta Key Condo

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$229

Excellent (2 reviews)

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from $229 / night

(1)

1 / 25

Siesta Key House

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

$326

Excellent (1 reviews)

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from $326 / night

1 / 24

Siesta Key Condo

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

from $215 / night

(5)

1 / 24

Siesta Key Condo

  • 2
  • 4
  • 7 nights min
  • Nearest beach 0.24 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

$79

Excellent (5 reviews)

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from $79 / night

1 / 24

Siesta Key Condo

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

from $229 / night

1 / 24

Siesta Key Condo

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

from $180 / night

(6)

1 / 20

Siesta Key House

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

$146

Excellent (6 reviews)

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from $146 / night

1 / 24

Siesta Key Condo

  • 2
  • 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $243 / night

1 / 24

Siesta Key Condo

  • 2
  • 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $243 / night