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Siesta Key Waterfront Beach Rentals, Vacation Rentals & More - 41 Rentals Available.

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41 Vacation rentals

Filters applied: Waterfront

(8)

1 / 22

Siesta Key Condo

  • 1
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“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 (8 reviews)

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from $147.00 / night

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(41)

1 / 24

Siesta Key Condo

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.25 mi
  • Swimming pool
“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

$104.00

Very Good (41 reviews)

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from $104.00 / night

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(27)

1 / 24

Siesta Key Condo

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
“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

$206.00

Excellent (27 reviews)

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from $206.00 / night

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(22)

1 / 31

Siesta Key Condo

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“My wife and I spent 2 weeks at this well kept and wonderfully located condominium. We loved that it is a garden style complex and not a high rise building. This unit being on the 1st floor makes it even better. Being able to walk right out to the...”
- Review left on 02/05/2021

$258.00

Excellent (22 reviews)

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(1)

1 / 23

Siesta Key Condo

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$352.00

Excellent (1 reviews)

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from $352.00 / night

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(7)

1 / 24

Siesta Key Condo

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.25 mi
  • Swimming pool
“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

$104.00

Excellent (7 reviews)

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from $104.00 / night

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(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

$104.00

Excellent (2 reviews)

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(2)

1 / 22

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

$373.00

Very Good (2 reviews)

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from $373.00 / 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

$243.00

Excellent (2 reviews)

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from $243.00 / night

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(6)

1 / 53

Siesta Key House

  • 3
  • 9
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly

$682.00

Excellent (6 reviews)

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from $682.00 / night

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(4)

1 / 25

Siesta Key Condo

  • 1
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

Responds fast! Avg. 2 hours 59 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

$161.00

Very Good (4 reviews)

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from $161.00 / night

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Your search has been expanded 19.7 miles to include more rentals

(40)

1 / 16

Sarasota Guest house - 3.7 miles away

  • 1
  • 2
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary
“My husband and I stayed in Joyce and Jeff's beautiful guest apartment for two weeks. Everything was perfect inside and out. The property was immaculate and the owners included extra touches that went above and beyond. While we spent most of our time...”
- Review left on 08/09/2017

$180.00

Excellent (40 reviews)

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(11)

1 / 20

Bradenton House - 15.6 miles away

  • 3
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“The location of this property is a perfect area. Just as described by the owner. House is fully equipped including a hand mixer. We enjoyed watching the water sports on the bay from the patio. Lots of parks and popular beaches within 5 mile radius...”
- Review left on 04/07/2017

$367.00

Very Good (11 reviews)

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from $367.00 / night

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(28)

1 / 20

Bradenton House - 15.4 miles away

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 15 mi
  • Child friendly

Responds fast! Avg. 1 hour 32 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 (28 reviews)

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from $150.00 / night

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1 / 28

Venice House - 18.3 miles away

  • 4
  • 8
  • 90 nights min
  • Beach/lakeside relaxation
  • Nearest beach 6 mi
  • Swimming pool

$191.00

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(1)

1 / 16

Bradenton Condo - 16.7 miles away

  • 3
  • 6
  • 120 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
“We vacationed at this villa during February and March 2011. It is spacious and quite nicely furnished. We especially enjoyed the setting - the view from every window is of trees and shrubs with no other dwellings visible. One minor drawback of its...”
- Review left on 04/28/2011

$107.00

Very Good (1 reviews)

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from $107.00 / night

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(9)

1 / 17

Sarasota Condo - 0.1 miles away

  • 2
  • 5
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“We had such a wonderful trip to Siesta Key! The condo was very nice. Beautifully decorated, very clean, and great location! Everything from booking it to checking out was very easy. Everything we needed was available to us, and more! Everybody...”
- Review left on 08/02/2016

$152.00

Excellent (9 reviews)

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(25)

1 / 42

Sarasota Condo - 0.1 miles away

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Not only is the location perfect, but the condo is more then perfect! Everything we needed for a week at the beach including beach chairs... towels etc! Couldn't have been a better vacation! Can't wait to book again... THANKYOU STEVE...”
- Review left on 10/17/2017

$172.00

Excellent (25 reviews)

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(21)

1 / 20

Sarasota Condo - 0.1 miles away

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“Found this property on the website and I'm glad I did. Ms Kathy is great! The property was beautiful. From the minute we walked in, the place is very nice and relaxing. Everything you need in the comfort of your home including beach equipments. Felt...”
- Review left on 07/20/2016

$114.00

Excellent (21 reviews)

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(3)

1 / 5

Bradenton House - 12.6 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 20 mi
  • Swimming pool
“we rented this home for a week in July, the home is beautiful, it is equipped with every thing you could possibly need. the pool area was very relaxing and enjoyable. we loved the hone and would rent again...”
- Review left on 07/13/2014

$167.00

Excellent (3 reviews)

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(4)

1 / 12

Bradenton House - 18.3 miles away

  • 3
  • 3
  • 13 nights min
  • Beach/lakeside relaxation
  • Nearest beach 30 mi
  • Swimming pool
“We enjoyed this house, and it was the warmest December on record! Went to the beach 3 times and the ocean was warm enough to swim in this year! Look forward to more trips to Florida...”
- Review left on 01/08/2016

$167.00

Excellent (4 reviews)

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(21)

1 / 28

Sarasota Villa - 4.1 miles away

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
“We really like this place. The beaches are the best ever!!! We had great time in family. 5 min walk to Costco and other store. House very clean, good for a familly of 6. We appreciate having a pool near the house for an evening activity after the...”
- Review left on 09/14/2016

$126.00

Excellent (21 reviews)

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(6)

1 / 24

Holmes Beach Condo - 18.3 miles away

  • 2
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“My Husband ,Son & I had a wonderful time at the Condo,it was clean ,comfortable & near the beach ,shops & the bus stops.I could not ask for anything better ,will be looking to rent again in the future”
- Review left on 09/01/2015

$155.00

Excellent (6 reviews)

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(1)

1 / 20

Venice House - 17.9 miles away

  • 2
  • 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
“This was a perfect retreat. Loved the set up, thete was plenty of room and had everything we needed. The boat even fit. Angie and Gary were awesome people and so were the neighbors. We truly felt as if we were iold friends. A couple of...”
- Review left on 06/19/2015

$136.00

Very Good (1 reviews)

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1 / 8

Sarasota Condo - 10.1 miles away

  • 1
  • 2
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 9 mi
  • Swimming pool

Responds fast! Avg. 3 hours 33 minutes

$57.00

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(2)

1 / 8

Sarasota Condo - 10.1 miles away

  • 1
  • 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 9 mi
  • Swimming pool

Responds fast! Avg. 3 hours 33 minutes

$63.00

Average (2 reviews)

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(7)

1 / 16

Holmes Beach Villa - 19 miles away

  • 3
  • 6
  • 7 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

$458.00

Very Good (7 reviews)

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(18)

1 / 24

Venice House - 16.5 miles away

  • 3
  • 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
“We stayed at this home for the month of March and were very happy with our stay. The home had everything we needed and the owner was very quick to respond to any of our questions both before and during our stay.The house is furnished in a bright...”
- Review left on 04/07/2015

$264.00

Excellent (18 reviews)

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(1)

1 / 16

Bradenton House - 11.9 miles away

  • 3
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool

$201.00

Excellent (1 reviews)

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(3)

1 / 34

Bradenton Condo - 12.8 miles away

  • 2
  • 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 12 mi
  • Swimming pool

$144.00

Excellent (3 reviews)

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(3)

1 / 31

Bradenton Beach Cottage - 16.7 miles away

  • 2
  • 5
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
“My husband and I spent the weekend in this cottage to celebrate his milestone birthday. We found it to be very comfortable and welcoming. I especially love the sunroom for my morning coffee and yoga. We were pleasantly surprised at how comfortable...”
- Review left on 11/23/2017

$189.00

Very Good (3 reviews)

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(3)

1 / 36

Bradenton Beach Cottage - 16.7 miles away

  • 2
  • 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$327.00

Excellent (3 reviews)

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from $327.00 / night

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(33)

1 / 86

Venice Condo - 13.7 miles away

  • 1
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“This place had everything you needed to feel right at home. Comfortable and cozy, when we walked in you could smell it was clean and it was very neat and tidy!!! TV's in all the rooms, AC worked great and it was quite along with the ceiling fans....”
- Review left on 05/02/2016

$161.00

Very Good (33 reviews)

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1 / 6

Venice House - 16 miles away

  • 2
  • 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$136.00

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(1)

1 / 26

Sarasota Cottage - 5.8 miles away

  • 1
  • 3
  • 7 nights min
  • Beach/lakeside relaxation
  • Air conditioning
  • Private garden

$172.00

Excellent (1 reviews)

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(3)

1 / 11

Sarasota Condo - 10.7 miles away

  • 2
  • 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 20 mi
  • Swimming pool

Responds fast! Avg. 3 hours 30 minutes

“This condo was extremely well appointed and had everything that we needed. We stayed 3 months and enjoyed every minute. The owners were gracious and responsive to every question. The view was outstanding. How much did we like it -we are renting it...”
- Review left on 03/30/2015

$115.00

Excellent (3 reviews)

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(31)

1 / 24

Anna Maria Island Cottage - 19.7 miles away

  • 2
  • 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 51 minutes

“Songbird is a little slice of heaven with everything we needed to have a comfortable stay. We stayed for one week. Joel, the owner, is very thoughtful, and accommodating, and he makes it known that he is there for you if you need him. Which is so...”
- Review left on 05/20/2017

$153.00

Excellent (31 reviews)

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1 / 26

Bradenton Beach Villa - 17.4 miles away

  • 4
  • 12
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$458.00

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(3)

1 / 16

Sarasota Condo - 10.1 miles away

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool

Responds fast! Avg. 3 hours 33 minutes

“We rented this two bedroom listed as a Condo, it is really two adjoining hotel rooms with kitchenettes. Nice accommodations, however the shower heads could be a little higher not convenient for taller people. Great view, right on Marina, close to the...”
- Review left on 01/23/2015

$171.00

Very Good (3 reviews)

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(2)

1 / 31

Anna Maria Island Cottage - 16.3 miles away

  • 1
  • 3
  • 2 nights min
  • Beach/lakeside relaxation
  • Car not necessary

$327.00

Very Good (2 reviews)

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from $327.00 / night

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