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Siesta Key Beach Rentals & Vacation Rentals with Swimming Pool - 221 Rentals Available.

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221 Vacation rentals

Filters applied: Swimming pool

(3)

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

$155

Excellent (3 reviews)

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from $155 / night

1 / 35

Siesta Key House

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

from $180 / 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

$136

Very Good (7 reviews)

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from $136 / night

1 / 33

Siesta Key House

  • 5
  • 13
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $251 / night

(1)

1 / 34

Siesta Key House

  • 3
  • 9
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$229

Excellent (1 reviews)

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from $229 / night

1 / 32

Siesta Key House

  • 5
  • 14
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $251 / 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

$180

Excellent (1 reviews)

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from $180 / night

(11)

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 (11 reviews)

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from $89 / night

1 / 33

Siesta Key Condo

  • 1
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $200 / night

1 / 35

Siesta Key House

  • 3
  • 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $207 / night

(1)

1 / 34

Siesta Key House

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

$180

Excellent (1 reviews)

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from $180 / night

1 / 24

Siesta Key House

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

from $215 / night

1 / 29

Siesta Key House

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

from $311 / night

(3)

1 / 11

Siesta Key Villa

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Great complex. Villa was very nice. Beds were comfortable. Had everything we needed. The beach is beautiful. Beach chairs provided. Didn't need to ever leave...”
- Review left on 07/05/2012

$144

Excellent (3 reviews)

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from $144 / night

1 / 25

Siesta Key House

  • 4
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $267 / night

1 / 24

Siesta Key Condo

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

from $129 / 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

$147

Excellent (6 reviews)

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from $147 / night

1 / 26

Siesta Key House

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

from $267 / night

(5)

1 / 37

Siesta Key House

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“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 (5 reviews)

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from $400 / night

(1)

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

$287

Very Good (1 reviews)

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from $287 / night

(8)

1 / 17

Siesta Key Condo

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“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

$144

Excellent (8 reviews)

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from $144 / night

(5)

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

$121

Excellent (5 reviews)

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from $121 / night

1 / 20

Siesta Key Villa

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

from $285 / night

1 / 30

Siesta Key House

  • 4
  • 14
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $267 / 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

$251

Excellent (2 reviews)

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from $251 / night

(1)

1 / 25

Siesta Key House

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

$327

Excellent (1 reviews)

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from $327 / night

1 / 31

Siesta Key House

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

from $300 / night

1 / 34

Siesta Key House

  • 4
  • 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $215 / night

1 / 24

Siesta Key Condo

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

from $180 / night

(4)

1 / 21

Siesta Key Condo

  • 1
  • 3
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“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

$196

Excellent (4 reviews)

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from $196 / night

1 / 24

Siesta Key Studio

  • -1
  • 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $100 / 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
  • Ask about children

from $243 / night

(5)

1 / 33

Siesta Key Condo

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

Excellent (5 reviews)

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from $165 / night

(33)

1 / 24

Siesta Key Condo

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“We stayed here with our three children. It surpassed our expectations. Very clean and up to date. The beach was just across the street a couple mins to walk to. The beach was just beautiful and the staff at Midnight Cove were very helpful...”
- Review left on 01/10/2012

$75

Excellent (33 reviews)

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from $75 / 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

$75

Excellent (5 reviews)

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from $75 / 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

$267

Very Good (5 reviews)

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from $267 / night

1 / 24

Siesta Key Villa

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

from $200 / 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
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $229 / night