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Siesta Key 2-bedroom Beach Rentals, Vacation Rentals & More - 322 Rentals Available.

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322 Vacation rentals

Filters applied: 2+ Bedrooms

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 / 38

Siesta Key House

  • 4
  • 12
  • 4 nights min
  • Child friendly

$380.00

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from $380.00 / 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

(2)

1 / 41

Siesta Key Condo

  • 2
  • 4
  • Min stay varies
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child friendly

$143.00

Excellent (2 reviews)

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from $143.00 / 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)

1 / 24

Siesta Key Condo

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

$170.00

Excellent (1 reviews)

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from $170.00 / 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

(5)

1 / 18

Siesta Key Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

$307.00

Excellent (5 reviews)

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from $307.00 / 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

1 / 33

Siesta Key House

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

$380.00

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from $380.00 / night

(9)

1 / 18

Siesta Key Condo

  • 2
  • 4
  • Min stay varies
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child friendly
“Great property, beautiful pool, super close to the beach and the village - will totally be back! Awesome property management as well...”
- Review left on 06/13/2016

$143.00

Excellent (9 reviews)

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from $143.00 / 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 / 21

Siesta Key House

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

$495.00

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from $495.00 / night

(3)

1 / 34

Siesta Key House

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

$200.00

Excellent (3 reviews)

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from $200.00 / 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

$115.00

Excellent (25 reviews)

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from $115.00 / 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

$146.00

Excellent (6 reviews)

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from $146.00 / night

1 / 20

Siesta Key Villa

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

$300.00

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from $300.00 / night

(4)

1 / 9

Siesta Key Condo

  • 2
  • 6
  • 7 nights min
  • Child friendly
  • Air conditioning
“I loved this condo a lot, it was so close to the beach, it was clean and everything was there for you”
- Review left on 11/04/2016

$99.00

Very Good (4 reviews)

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from $99.00 / night

1 / 43

Siesta Key House

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

$310.00

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from $310.00 / 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 / 24

Siesta Key Condo

  • 2
  • 5
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$180.00

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from $180.00 / night

(1)

1 / 24

Siesta Key Condo

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

$272.00

Excellent (1 reviews)

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from $272.00 / 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

$1,000.00

Excellent (7 reviews)

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from $1,000.00 / 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 / 66

Siesta Key House

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

$712.00

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from $712.00 / night

1 / 10

Siesta Key House

  • 4
  • 10
  • Min stay varies
  • Child friendly

$256.00

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from $256.00 / night

(1)

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

$200.00

Excellent (1 reviews)

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from $200.00 / night

(1)

1 / 24

Siesta Key Condo

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

$272.00

Excellent (1 reviews)

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from $272.00 / night

(3)

1 / 38

Siesta Key House

  • 5
  • 13
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$625.00

Excellent (3 reviews)

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from $625.00 / night

1 / 25

Siesta Key House

  • 3
  • 6
  • Min stay varies
  • Child friendly
  • Pet friendly

$170.00

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from $170.00 / night

(5)

1 / 33

Siesta Key Condo

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.001 mi
  • Swimming pool
“My family of 3 stumbled across Fish Cove while searching for a vacation destination in Florida. It really looked too good to be true, but I can assure you that it did delivered and surpassed every expectation we had set! I worked to plan our visit...”
- Review left on 12/26/2016

$165.00

Excellent (5 reviews)

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from $165.00 / night

1 / 24

Siesta Key Condo

  • 2
  • 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$170.00

Inquire

from $170.00 / night

1 / 24

Siesta Key House

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

$214.00

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from $214.00 / night

(7)

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

$458.00

Excellent (7 reviews)

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from $458.00 / night

(2)

1 / 41

Siesta Key Condo

  • 2
  • 5
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“Our stay at Siesta Palms was great. The condo was very clean and up to date. We enjoyed the beautiful pool and proximity to the beach. The owners couldn't have been kinder or more accommodating. I highly recommend this condo...”
- Review left on 04/15/2016

$257.00

Excellent (2 reviews)

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from $257.00 / night

1 / 24

Siesta Key Condo

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$229.00

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from $229.00 / night

1 / 24

Siesta Key Condo

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

$243.00

Inquire

from $243.00 / night

(3)

1 / 15

Siesta Key Villa

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“This property was beautiful. Clean, spacious, close to the gulf and the pool. The beach was amazing! I definitely see why it was voted #1 beach in USA. We rented bikes - what a great deal ... the rental was located just before entrance to Siesta key...”
- Review left on 01/05/2013

$154.00

Excellent (3 reviews)

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from $154.00 / night

1 / 40

Siesta Key House

  • 4
  • 12
  • Min stay varies
  • Child friendly

$380.00

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from $380.00 / night

1 / 24

Siesta Key Condo

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

$158.00

Inquire

from $158.00 / night