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Siesta Key Waterfront Beach Rentals, Vacation Rentals & More - 160 Rentals Available.

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160 Vacation rentals

Filters applied: Waterfront

(6)

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

$85.00

Excellent (6 reviews)

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from $85.00 / night

(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

$85.00

Excellent (38 reviews)

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from $85.00 / night

(27)

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

$141.00

Excellent (27 reviews)

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from $141.00 / night

(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

(5)

1 / 51

Siesta Key House

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

$453.00

Excellent (5 reviews)

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from $453.00 / night

(9)

1 / 38

Siesta Key House

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

$516.00

Excellent (9 reviews)

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from $516.00 / 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

$89.00

Excellent (12 reviews)

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from $89.00 / night

(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

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

(2)

1 / 24

Siesta Key Apartment

  • 3
  • 8
  • min stay varies
  • Child friendly

Responds fast! Avg. 3 hours 16 minutes

$602.00

Excellent (2 reviews)

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from $602.00 / night

(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

(4)

1 / 23

Siesta Key House

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

$682.00

Excellent (4 reviews)

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from $682.00 / night

(2)

1 / 10

Siesta Key Condo

  • 1
  • 4
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“FIVE STARS!!!!! Terry the owner is a great guy that insured our stay in his condo went well. The condo has a great location just a couple of blocks from the Siesta Key Beach. The condo has everything you need for a great beach experience. The...”
- Review left on 01/24/2017

$87.00

Excellent (2 reviews)

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from $87.00 / night

(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

(7)

1 / 22

Siesta Key Condo

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

Responds fast! Avg. 3 hours 12 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

1 / 14

Siesta Key Condo

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

$114.00

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from $114.00 / night

(7)

1 / 31

Siesta Key Condo

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

$236.00

Excellent (7 reviews)

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from $236.00 / night

(6)

1 / 21

Siesta Key Condo

  • 1
  • 3
  • 14 nights min
  • 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

$272.00

Excellent (6 reviews)

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from $272.00 / night

1 / 14

Siesta Key Apartment

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

Responds fast! Avg. 3 hours 16 minutes

$258.00

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from $258.00 / night

(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

$175.00

Excellent (10 reviews)

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from $175.00 / night

(4)

1 / 41

Siesta Key Condo

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

$175.00

Excellent (4 reviews)

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from $175.00 / night

1 / 28

Siesta Key Apartment

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

Responds fast! Avg. 3 hours 16 minutes

$573.00

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from $573.00 / night

(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

(4)

1 / 24

Siesta Key Condo

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

(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

(7)

1 / 15

Siesta Key House

  • 4
  • 14
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • 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

$982.00

Excellent (7 reviews)

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from $982.00 / night

(2)

1 / 28

Siesta Key House

  • 3
  • 7
  • 14 nights min
  • 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

$262.00

Very Good (2 reviews)

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from $262.00 / night

(1)

1 / 23

Siesta Key Condo

  • 3
  • 6
  • min stay varies
  • Child friendly
  • Air conditioning

Responds fast! Avg. 42 minutes

$270.00

Excellent (1 reviews)

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from $270.00 / night

Your search has been expanded 19 miles to include more rentals

1 / 79

Bradenton Beach Condo - 16.8 miles away

  • 2
  • 6
  • min stay varies
  • Child friendly

Responds fast! Avg. 3 hours 29 minutes

$189.00

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from $189.00 / night

(7)

1 / 16

Holmes Beach Villa - 19 miles away

  • 3
  • 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Five of us and two dogs spent last week of July here, Great location, 8 iron golf shot to the beach from front yard, fantastic pool in back yard complete with all the toys you need for the beach or pool in garage, also refrigerator in garage to save...”
- Review left on 08/27/2015

$287.00

Very Good (7 reviews)

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from $287.00 / night

(22)

1 / 15

Bradenton Condo - 12.9 miles away

  • 2
  • 6
  • 6 nights min
  • Nearest beach 8 mi
  • Swimming pool
  • Child friendly
“Anita and Joe were great hosts and wonderful people! The condo is in a secure location close to lots of entertainment, attractions, and shopping. The neighborhood was quiet and friendly with lots of exercise walkers and dog walkers. We spent most...”
- Review left on 02/02/2017

$144.00

Very Good (22 reviews)

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from $144.00 / night

1 / 6

Venice House - 16 miles away

  • 2
  • 6
  • min stay varies
  • Ask about children
  • Air conditioning
  • Private garden

$129.00

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from $129.00 / night

(25)

1 / 24

Bradenton House - 15.4 miles away

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 15 mi
  • Swimming pool

Responds fast! Avg. 1 hour 36 minutes

“The location of this house is really outstanding. We enjoyed being on the river, watching the beautiful sunsets daily, watching birds come and go into the inlets. It is a private place within a lovely subdivision with lakes and riverfront. We also...”
- Review left on 02/02/2017

$150.00

Excellent (25 reviews)

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from $150.00 / night

(12)

1 / 23

Bradenton House - 17.7 miles away

  • 3
  • 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“My stay was from July 2- July 16 and I absolutely loved it. The rooms and bathrooms were super clean. Kitchen has all the appliances you needed it, home came with shower towels and amazing air conditioning through the vents. The neighborhood was...”
- Review left on 07/17/2016

$279.00

Excellent (12 reviews)

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from $279.00 / night

(1)

1 / 26

Sarasota House - 1.7 miles away

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“My wife, two boys and I stayed here for a week for my wife and sons birthday. We had a great time and everything was as advertised. The pool and beach are right there, the house was cozy and everything was great. We even had cupcakes waiting upon our...”
- Review left on 05/23/2016

$185.00

Excellent (1 reviews)

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from $185.00 / night

(3)

1 / 34

Bradenton Condo - 12.8 miles away

  • 2
  • 6
  • 3 nights min
  • Nearest beach 12 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 2 hours 26 minutes

$144.00

Excellent (3 reviews)

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from $144.00 / night

(27)

1 / 11

Bradenton House - 12.8 miles away

  • 4
  • 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“The home was a great place for our group to stay. It was clean and well maintained. The location was ideal, close to golf courses and shopping and many good restaurants. We would definitely stay there again. The owner, Larry was very good to work...”
- Review left on 02/01/2017

$210.00

Excellent (27 reviews)

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from $210.00 / night

1 / 15

Sarasota House - 6.2 miles away

  • 2
  • 4
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

Responds fast! Avg. 2 hours 26 minutes

$104.00

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from $104.00 / night

(7)

1 / 15

Bradenton Apartment - 11.8 miles away

  • 1
  • 2
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Air conditioning

Responds fast! Avg. 3 hours 15 minutes

“What a fantastic place. We had the pleasure of staying in Bob?s studio. Bob thought of everything to make our stay as close to home as possible. We couldn?t have asked for more. The surroundings are pure Florida. The grounds near the studio were well...”
- Review left on 11/19/2016

$144.00

Very Good (7 reviews)

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from $144.00 / night

(2)

1 / 35

Sarasota House - 3.2 miles away

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Loved the location of Casa Antigua. Very peaceful yet only a short drive to shops and beaches. Really enjoyed having a private pool and swam nearly every day (water little bit chilly at start of week but gradually warmed up once heater put on)....”
- Review left on 12/01/2016

$165.00

Very Good (2 reviews)

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from $165.00 / night