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Siesta Key Waterfront Beach Rentals, Vacation Rentals & More - 146 Rentals Available.

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146 Vacation rentals

Filters applied: Waterfront

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

from $129 / night

(10)

1 / 16

Siesta Key Condo

  • 1
  • 4
  • Min stay varies
  • 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

$144

Very Good (10 reviews)

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from $144 / night

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

1 / 29

Siesta Key House

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

$525

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from $525 / 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

(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

$266

Very Good (5 reviews)

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from $266 / night

1 / 24

Siesta Key Condo

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

from $186 / night

1 / 5

Siesta Key House

  • 3
  • 7
  • Min stay varies
  • 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

$229

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from $229 / night

1 / 24

Siesta Key Condo

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

from $150 / 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

$75

Excellent (33 reviews)

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from $75 / 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 / 24

Siesta Key Condo

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

from $229 / 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

$186

Excellent (1 reviews)

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from $186 / 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 / 24

Siesta Key Condo

  • 1
  • 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

from $160 / 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

(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

(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

Very Good (4 reviews)

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from $99 / night

1 / 24

Siesta Key Condo

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

from $243 / night

1 / 31

Siesta Key House

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

from $300 / night

1 / 36

Siesta Key Condo

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

from $400 / night

(3)

1 / 18

Siesta Key Condo

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

$229

Excellent (3 reviews)

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from $229 / 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

Excellent (25 reviews)

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from $115 / night

1 / 29

Siesta Key House

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

from $310 / night

1 / 26

Siesta Key House

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

from $266 / 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

(8)

1 / 30

Siesta Key Condo

  • 2
  • 4
  • Min stay varies
  • Nearest beach 0.25 mi
  • 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

$118

Excellent (8 reviews)

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from $118 / night

1 / 24

Siesta Key Condo

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

from $215 / night

1 / 35

Siesta Key House

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

from $179 / night

1 / 24

Siesta Key Condo

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

from $180 / 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

Excellent (5 reviews)

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from $165 / 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

(9)

1 / 10

Siesta Key Apartment

  • 1
  • 3
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
“The place was in the perfect spot and couldn't have been better. Very clean, great location. Would definitely stay again...”
- Review left on 04/22/2016

$140

Very Good (9 reviews)

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from $140 / night

1 / 24

Siesta Key Condo

  • 1
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $195 / night

(2)

1 / 24

Siesta Key Condo

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“We had a larger group but with the 3 beds and plenty of living space never felt cramped. It's a super short walk to the beach and having a full kitchen with a lot of accessories made for an easy and fun trip! We had one of the showers draining slow...”
- Review left on 08/01/2016

$195

Average (2 reviews)

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from $195 / night

(3)

1 / 11

Siesta Key Villa

  • 2
  • 6
  • 7 nights min
  • 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

$144

Excellent (3 reviews)

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from $144 / night

1 / 24

Siesta Key Condo

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

from $180 / night

(5)

1 / 21

Siesta Key Condo

  • 1
  • 3
  • Min stay varies
  • 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

$195

Excellent (5 reviews)

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from $195 / night

(1)

1 / 24

Siesta Key Condo

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

$180

Excellent (1 reviews)

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from $180 / night