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Siesta Key Beach Beach Rentals, Vacation Rentals & More - 52 Rentals Available.

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52 Vacation rentals

Filters applied: Beach

(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

$120.00

Very Good (13 reviews)

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from $120.00 / 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

(4)

1 / 33

Siesta Key House

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

$395.00

Excellent (4 reviews)

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from $395.00 / 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

$125.00

Excellent (9 reviews)

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from $125.00 / 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

(1)

1 / 31

Siesta Key House

  • 3
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 42 minutes

$380.00

Excellent (1 reviews)

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from $380.00 / night

(6)

1 / 17

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

(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

(2)

1 / 28

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

$229.00

Very Good (2 reviews)

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from $229.00 / night

(3)

1 / 52

Siesta Key House

  • 5
  • 12
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.75 mi
  • Swimming pool

Responds fast! Avg. 3 hours 42 minutes

“Beautiful home with so many added features! We are definitely coming back and staying at The Grand Canal...”
- Review left on 10/20/2015

$375.00

Excellent (3 reviews)

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from $375.00 / night

(7)

1 / 15

Siesta Key House

  • 4
  • 14
  • min stay varies
  • 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

$750.00

Excellent (7 reviews)

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from $750.00 / night

(2)

1 / 56

Siesta Key Villa

  • 4
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 42 minutes

$310.00

Average (2 reviews)

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from $310.00 / night

Your search has been expanded 18.9 miles to include more rentals

(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

$243.00

Excellent (12 reviews)

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from $243.00 / 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 35 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

(3)

1 / 33

Bradenton Beach Cottage - 16.7 miles away

  • 2
  • 4
  • min stay varies
  • 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

$150.00

Very Good (3 reviews)

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from $150.00 / night

(10)

1 / 8

Venice Condo - 18.9 miles away

  • 2
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“we had a good time, condo has been nice, pool close by . All together we enjoyed it, not to fare from the beach...”
- Review left on 11/27/2016

$100.00

Very Good (10 reviews)

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from $100.00 / night

1 / 8

Sarasota Condo - 10.1 miles away

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

$49.00

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from $49.00 / night

(5)

1 / 92

Anna Maria Island Condo - 16.8 miles away

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“The unit was well equipped with a good kitchen and lots of seating. TV's where great. We have two kids so we needed a place that could work for at home cooking as well. The location was perfect for us. The balcony was a perfect place for having a...”
- Review left on 01/05/2016

$157.00

Very Good (5 reviews)

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from $157.00 / night

(2)

1 / 16

Sarasota Condo - 10.1 miles away

  • 2
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool
“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

$99.00

Very Good (2 reviews)

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from $99.00 / night

1 / 17

Longboat Key House - 14.4 miles away

  • 6
  • 20
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary

$1,100.00

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from $1,100.00 / night

1 / 53

Holmes Beach House - 18.6 miles away

  • 6
  • 14
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$499.00

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from $499.00 / night

(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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from $152.00 / night

(1)

1 / 31

Anna Maria Island Cottage - 16.3 miles away

  • 1
  • 3
  • min stay varies
  • Beach/lakeside relaxation

$195.00

Excellent (1 reviews)

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from $195.00 / night

1 / 81

Anna Maria Island Condo - 16.8 miles away

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

$165.00

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from $165.00 / night

1 / 70

Anna Maria Island Condo - 15.8 miles away

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary

$200.00

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from $200.00 / night

1 / 29

Cortez Townhouse - 16.4 miles away

  • 4
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$295.00

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from $295.00 / night

(1)

1 / 78

Anna Maria Island Condo - 18.6 miles away

  • 1
  • 3
  • 6 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“As this was my first time to Anna Maria I was pleasantly surprised how very nice it is. My accommodations were above what I expected. The location is perfect for going to the beach, shopping, dining, or just relaxing by the pool. I enjoyed my stay so...”
- Review left on 03/10/2015

$143.00

Excellent (1 reviews)

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from $143.00 / night

(3)

1 / 18

Sarasota Condo - 3.1 miles away

  • 2
  • 6
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool

Responds fast! Avg. 2 hours 29 minutes

“We came to Sarasota for the first time in June and couldn't have picked a better condo! Location is great, condo was clean and spacious, and parking was easy. Overall very pleased and would definitely stay again...”
- Review left on 08/24/2017

$85.00

Very Good (3 reviews)

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from $85.00 / night

(1)

1 / 8

Sarasota Condo - 10.1 miles away

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

$55.00

Very Good (1 reviews)

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from $55.00 / night

(2)

1 / 36

Bradenton Beach Cottage - 16.7 miles away

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

$150.00

Excellent (2 reviews)

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from $150.00 / night

(2)

1 / 22

Longboat Key Condo - 11.4 miles away

  • 3
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
“This was a family holiday including 2 grandchildren, who loved every minute of the holiday and did not want to leave. Lovely 3 bedrooms condo in garden grounds, which lead to the beach, family swimming pool and adult pool and spa. 8 tennis courts....”
- Review left on 01/26/2017

$215.00

Very Good (2 reviews)

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from $215.00 / night

(33)

1 / 180

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

$70.00

Very Good (33 reviews)

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from $70.00 / night

(2)

1 / 11

Cortez Cottage - 16.4 miles away

  • 2
  • 4
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.25 mi
  • Air conditioning
“This apartment had a beautiful open concept, nicely decorated. The place was supplied with nice quality furniture and cooking apparatus. Quiet and right on the canal, close to everything. Owners were above and beyond for help, and just a click...”
- Review left on 01/02/2015

$117.00

Very Good (2 reviews)

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from $117.00 / night

(5)

1 / 21

Sarasota Condo - 2.6 miles away

  • 2
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 6 mi
  • Swimming pool

Responds fast! Avg. 2 hours 41 minutes

“Centrally located in Sarasota, near to everything. The Siesta Key Beach is just few minutes driving. The condo is directly on a lake, plenty of wild birds are patrolling the area, and early morneing even a sweet otter family walked by. The place is...”
- Review left on 02/26/2018

$79.00

Excellent (5 reviews)

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from $79.00 / night

(9)

1 / 100

Anna Maria Island Condo - 16.6 miles away

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Hidden Oasis is a lovely property - nicely decorated, very clean, very well-kept, and equipped with pretty much everything you might need or want. It also has a fantastic view of the gulf and the beach; and this view is visible from the living room...”
- Review left on 03/16/2017

$200.00

Excellent (9 reviews)

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from $200.00 / night

(7)

1 / 15

Bradenton Apartment - 11.8 miles away

  • 1
  • 2
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Ask about children

Responds fast! Avg. 1 hour 47 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

$125.00

Very Good (7 reviews)

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from $125.00 / night

(21)

1 / 20

Sarasota Condo - 0.1 miles away

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • 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

$105.00

Excellent (21 reviews)

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from $105.00 / night

1 / 59

Sarasota Condo - 0.1 miles away

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

$135.00

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from $135.00 / night

(3)

1 / 24

Sarasota Townhouse - 0.1 miles away

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“The house was nice but a little out dated. A few things went wrong, but the owner really helped out immediately to rectify all the problems. It had all the things you wanted for the beach except an umbrella, which if we had one, we would have...”
- Review left on 06/04/2013

$358.00

Very Good (3 reviews)

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from $358.00 / night

1 / 24

Bradenton Beach Condo - 16.6 miles away

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

$200.00

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from $200.00 / night