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Siesta Key Waterfront Beach Rentals, Vacation Rentals & More - 324 Rentals Available.

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324 Vacation rentals

Filters applied: Waterfront

(38)

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

$88.00

Excellent (38 reviews)

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from $88.00 / night

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(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

$88.00

Excellent (5 reviews)

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from $88.00 / night

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(26)

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

$147.00

Excellent (26 reviews)

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from $147.00 / night

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(13)

1 / 17

Siesta Key Condo

  • 1
  • 4
  • 7 nights min
  • 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

$135.00

Very Good (13 reviews)

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from $135.00 / night

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(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

$89.00

Excellent (12 reviews)

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from $89.00 / night

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(4)

1 / 51

Siesta Key House

  • 3
  • 9
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly

$453.00

Excellent (4 reviews)

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from $453.00 / night

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(8)

1 / 38

Siesta Key House

  • 5
  • 13
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$516.00

Excellent (8 reviews)

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from $516.00 / 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

$193.00

Excellent (2 reviews)

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from $193.00 / night

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(2)

1 / 24

Siesta Key Apartment

  • 3
  • 8
  • min stay varies
  • Child friendly

Responds fast! Avg. 2 hours 25 minutes

$602.00

Excellent (2 reviews)

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from $602.00 / night

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1 / 33

Siesta Key Condo

  • 1
  • 4
  • min stay varies
  • Nearest beach 0.09 mi
  • Swimming pool
  • Ask about children

$228.00

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from $228.00 / night

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(9)

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

$130.00

Excellent (9 reviews)

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from $130.00 / night

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(2)

1 / 23

Siesta Key House

  • 4
  • 12
  • 7 nights min
  • Nearest beach 0.2 mi
  • Swimming pool
  • Child friendly

$682.00

Excellent (2 reviews)

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from $682.00 / night

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(1)

1 / 39

Siesta Key House

  • 4
  • 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$395.00

Excellent (1 reviews)

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from $395.00 / night

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1 / 40

Siesta Key House

  • 4
  • 8
  • min stay varies
  • Child friendly
  • Pet friendly

$260.00

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from $260.00 / night

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1 / 39

Siesta Key House

  • 2
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 27 minutes

$225.00

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from $225.00 / night

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1 / 14

Siesta Key Condo

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$114.00

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from $114.00 / night

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(5)

1 / 24

Siesta Key Condo

  • 1
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“Thank you for a wonderful week! The room was beautiful and Mary Ann and staff were all so accommodating to anything that you may need! We would highly recommend Siesta Palms to everyone! We are looking forward to coming back as soon as possible,...”
- Review left on 07/13/2016

$228.00

Excellent (5 reviews)

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from $228.00 / night

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(7)

1 / 22

Siesta Key Condo

  • 1
  • 4
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 20 minutes

“We stayed for a week and had the best time ever. The accommodations are top notch, locals are very friendly, food delicious and breathtaking beaches. Definitely looking forward to coming back”
- Review left on 12/15/2015

$147.00

Excellent (7 reviews)

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from $147.00 / night

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(6)

1 / 31

Siesta Key Condo

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

$236.00

Excellent (6 reviews)

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from $236.00 / night

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1 / 40

Siesta Key House

  • 2
  • 6
  • min stay varies
  • Child friendly
  • Pet friendly

$185.00

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from $185.00 / night

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1 / 24

Siesta Key Cottage

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$185.00

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from $185.00 / night

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(4)

1 / 41

Siesta Key Condo

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

$144.00

Excellent (4 reviews)

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from $144.00 / night

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(6)

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

$200.00

Excellent (6 reviews)

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from $200.00 / night

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(1)

1 / 26

Siesta Key House

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

$325.00

Excellent (1 reviews)

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from $325.00 / night

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1 / 29

Siesta Key House

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 27 minutes

$185.00

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from $185.00 / night

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(1)

1 / 25

Siesta Key Cottage

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$168.00

Excellent (1 reviews)

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from $168.00 / night

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1 / 27

Siesta Key House

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 27 minutes

$150.00

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from $150.00 / night

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1 / 43

Siesta Key House

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

$325.00

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from $325.00 / night

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1 / 39

Siesta Key House

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

Responds fast! Avg. 3 hours 27 minutes

$250.00

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from $250.00 / night

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(8)

1 / 30

Siesta Key Condo

  • 2
  • 4
  • 7 nights min
  • 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

$121.00

Excellent (8 reviews)

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from $121.00 / night

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1 / 14

Siesta Key Apartment

  • 1
  • 4
  • min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning

Responds fast! Avg. 2 hours 25 minutes

$258.00

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from $258.00 / night

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(10)

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

$144.00

Excellent (10 reviews)

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from $144.00 / night

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1 / 33

Siesta Key Townhouse

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$255.00

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from $255.00 / night

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1 / 33

Siesta Key House

  • 3
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 27 minutes

$255.00

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from $255.00 / night

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(4)

1 / 24

Siesta Key Condo

  • 1
  • 4
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning

Responds fast! Avg. 3 hours 50 minutes

“This place is absolutely great. Me and my girlfriend spent two nights over the weekend at this condo. First of all this place has more stuff that we could imagine. It literally includes everything you need for having a pleasant and comfortable stay....”
- Review left on 07/26/2016

$104.00

Very Good (4 reviews)

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from $104.00 / night

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1 / 45

Siesta Key House

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$250.00

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from $250.00 / night

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1 / 40

Siesta Key House

  • 4
  • 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$395.00

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from $395.00 / night

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1 / 28

Siesta Key Apartment

  • 2
  • 8
  • min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning

Responds fast! Avg. 2 hours 25 minutes

$602.00

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from $602.00 / night

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1 / 31

Siesta Key House

  • 4
  • 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$325.00

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from $325.00 / night

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(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

$311.00

Excellent (2 reviews)

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from $311.00 / night

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