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Siesta Key Beach Beach Rentals, Vacation Rentals & More - 44 Rentals Available.

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44 Vacation rentals

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(5)

1 / 51

Siesta Key House

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

$516.00

Excellent (5 reviews)

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from $516.00 / 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

(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

(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

(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

(8)

1 / 31

Siesta Key Condo

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“This condo is beautifully decorated with top notch fixtures and is very clean. It is a 2 minute walk from the beach, and even though the pool and hot tub are a 30 second walk from the patio, we were never bothered by any noise from the pool. The...”
- Review left on 04/26/2019

$236.00

Excellent (8 reviews)

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from $236.00 / 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

(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

Your search has been expanded 19 miles to include more rentals

(57)

1 / 13

Longboat Key House - 12.3 miles away

  • 4
  • 10
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly

Responds fast! Avg. 3 hours 29 minutes

“Great family vacation in a spacious and clean home with kids in their own rooms, full kitchen and close to the beach and to restaurants and activities. The January weather was awesome, 75-80 each day without rain.Likely return next year.Resort has...”
- Review left on 01/22/2017

$224.00

Very Good (57 reviews)

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from $224.00 / night

(3)

1 / 33

Bradenton Beach Cottage - 16.7 miles away

  • 2
  • 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly

Responds fast! Avg. 1 hour 36 minutes

“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

$172.00

Very Good (3 reviews)

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from $172.00 / 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

$134.00

Very Good (2 reviews)

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from $134.00 / night

(10)

1 / 6

Venice Condo - 18.9 miles away

  • 2
  • 5
  • 7 nights min
  • 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

$114.00

Very Good (10 reviews)

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from $114.00 / night

(2)

1 / 16

Sarasota Condo - 10.1 miles away

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

Responds fast! Avg. 3 hours 21 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

$114.00

Very Good (2 reviews)

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from $114.00 / night

(1)

1 / 40

Sarasota House - 1.1 miles away

  • 6
  • 12
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

Responds fast! Avg. 2 hours 50 minutes

$646.00

Very Good (1 reviews)

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from $646.00 / night

(2)

1 / 36

Bradenton Beach Cottage - 16.7 miles away

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

Responds fast! Avg. 1 hour 36 minutes

$172.00

Excellent (2 reviews)

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from $172.00 / night

1 / 59

Sarasota Condo - 0.1 miles away

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

Responds fast! Avg. 2 hours 35 minutes

$212.00

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from $212.00 / 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

(4)

1 / 19

Bradenton Villa - 17.6 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“House was a great location for our Needs. Very Clean and spacious. Heated Pool was a great asset.. Would have liked a bigger more useable grill...”
- Review left on 02/23/2017

$180.00

Excellent (4 reviews)

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from $180.00 / night

1 / 20

Bradenton Beach Condo - 16.3 miles away

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

$655.00

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from $655.00 / 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 48 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

1 / 29

Cortez Townhouse - 16.4 miles away

  • 4
  • 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 36 minutes

$338.00

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from $338.00 / night

(2)

1 / 22

Longboat Key Condo - 11.4 miles away

  • 3
  • 6
  • 14 nights min
  • 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

(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

$458.00

Very Good (3 reviews)

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from $458.00 / 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

(4)

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. 3 hours 13 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

$98.00

Very Good (4 reviews)

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from $98.00 / night

(5)

1 / 125

Anna Maria Island Condo - 16.8 miles away

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

Responds fast! Avg. 2 hours 25 minutes

“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

$344.00

Very Good (5 reviews)

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from $344.00 / night

(7)

1 / 15

Bradenton Apartment - 11.8 miles away

  • 1
  • 2
  • 5 nights min
  • 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

(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

$109.00

Very Good (33 reviews)

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from $109.00 / night

(6)

1 / 17

Sarasota Apartment - 1.1 miles away

  • 1
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary

Responds fast! Avg. 3 hours 16 minutes

“This was perfect for a 1 person quick getaway. It would also be great for an extended stay. Very clean and tastefully furnished. Easy walk to dining and shopping. Very easy drive to Sarasota attractions. But, once you're on Siesta, there's really no...”
- Review left on 02/24/2014

$287.00

Very Good (6 reviews)

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from $287.00 / night

(15)

Certificate of Excellence

1 / 24

Venice House - 16.5 miles away

  • 3
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool

Responds fast! Avg. 1 hour 49 minutes

Certificate of Excellence

“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

$102.00

Excellent (15 reviews)

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from $102.00 / night

(1)

1 / 8

Sarasota Condo - 10.1 miles away

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

Responds fast! Avg. 3 hours 21 minutes

$63.00

Very Good (1 reviews)

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from $63.00 / night

(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

$229.00

Very Good (7 reviews)

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from $229.00 / night

(1)

1 / 28

Sarasota House - 1.1 miles away

  • 3
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 16 minutes

“The Beach House was exactly what we anticipated: clean, comfortable, cute and perfectly located on the beach. The lawn, fire ring, hammocks, children's play area and lawn furniture were extras that added a lot. The kitchen was large enough for...”
- Review left on 03/06/2014

$584.00

Excellent (1 reviews)

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from $584.00 / night

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 21 minutes

$57.00

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from $57.00 / night

(1)

1 / 31

Anna Maria Island Cottage - 16.3 miles away

  • 1
  • 3
  • 2 nights min
  • Beach/lakeside relaxation

Responds fast! Avg. 2 hours 3 minutes

$224.00

Excellent (1 reviews)

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from $224.00 / night

(9)

1 / 100

Anna Maria Island Condo - 16.6 miles away

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

Responds fast! Avg. 2 hours 25 minutes

“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

$401.00

Excellent (9 reviews)

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from $401.00 / night

1 / 81

Anna Maria Island Condo - 16.8 miles away

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

Responds fast! Avg. 2 hours 25 minutes

$396.00

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from $396.00 / night

(5)

1 / 93

Anna Maria Island House - 16.6 miles away

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

Responds fast! Avg. 2 hours 25 minutes

“We enjoyed our stay at this property. The home is well decorated and all rooms are very spacious. The master bedroom is enormous with jacuzzi and large walk-in shower. The other bedrooms are very spacious too. Our manager resolved a few minor...”
- Review left on 08/10/2016

$516.00

Excellent (5 reviews)

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from $516.00 / 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

Responds fast! Avg. 2 hours 25 minutes

“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

$164.00

Excellent (1 reviews)

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from $164.00 / night

1 / 70

Anna Maria Island Condo - 15.8 miles away

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary

Responds fast! Avg. 2 hours 25 minutes

$344.00

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from $344.00 / night