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Longboat Key 2-bedroom Vacation Rentals, Apartments & More - 328 Rentals Available.

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328 Vacation rentals

Filters applied: 2+ Bedrooms

(2)

1 / 22

Longboat Key Condo

  • 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

(57)

1 / 13

Longboat Key House

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

Your search has been expanded 14.4 miles to include more rentals

(26)

1 / 24

Siesta Key Condo - 9.8 miles away

  • 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

(4)

1 / 19

Bradenton Villa - 14.4 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

(12)

1 / 23

Bradenton House - 14.1 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 / 24

Sarasota Cottage - 12.4 miles away

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

$190.00

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from $190.00 / night

(12)

1 / 40

Siesta Key Condo - 8.6 miles away

  • 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

(4)

1 / 51

Siesta Key House - 8 miles away

  • 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

(8)

1 / 38

Siesta Key House - 8.3 miles away

  • 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

(25)

1 / 24

Bradenton House - 11.1 miles away

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

Responds fast! Avg. 1 hour 39 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

(2)

1 / 16

Siesta Key Condo - 9.5 miles away

  • 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)

1 / 21

Anna Maria House - 13.6 miles away

  • 3
  • 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly

Responds fast! Avg. 1 hour 15 minutes

$573.00

Excellent (1 reviews)

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from $573.00 / night

1 / 19

Palma Sola House - 10 miles away

  • 4
  • 8
  • 7 nights min
  • Child friendly

$158.00

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from $158.00 / night

1 / 12

Bradenton House - 9.8 miles away

  • 5
  • 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$246.00

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from $246.00 / night

(23)

1 / 23

Anna Maria Island Cottage - 11.4 miles away

  • 2
  • 5
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden

Responds fast! Avg. 1 hour 26 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

$104.00

Excellent (23 reviews)

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from $104.00 / night

1 / 26

Bradenton House - 9.6 miles away

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

$158.00

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from $158.00 / night

1 / 8

Anna Maria Island Apartment - 7.9 miles away

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

$252.00

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from $252.00 / night

(18)

1 / 12

Bradenton House - 14.4 miles away

  • 4
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Superbly equipped villa in a great location. Immaculately clean with high spec kitchen which was equipped extremely well with good quality appliances. Pool area nice with fab spa overlooking lake and big outside dining area which was used all the...”
- Review left on 08/07/2016

$279.00

Excellent (18 reviews)

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from $279.00 / night

1 / 39

Siesta Key House - 7.9 miles away

  • 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

(6)

1 / 31

Siesta Key Condo - 9.4 miles away

  • 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

(2)

1 / 18

Sarasota Villa - 12 miles away

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

Responds fast! Avg. 3 hours 48 minutes

“The condo was perfect for our stay. Plenty of room to spread out and everyone had their own space. Highly recommend...”
- Review left on 07/22/2015

$98.00

Excellent (2 reviews)

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from $98.00 / night

(4)

1 / 41

Siesta Key Condo - 7.6 miles away

  • 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

1 / 29

Siesta Key House - 10.2 miles away

  • 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

(3)

1 / 16

Bradenton House - 10.4 miles away

  • 3
  • 6
  • min stay varies
  • Nearest beach 20 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 50 minutes

“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

$144.00

Excellent (3 reviews)

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from $144.00 / night

(7)

1 / 16

Holmes Beach Villa - 10.7 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

1 / 39

Siesta Key House - 10.6 miles away

  • 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

1 / 29

Cortez Townhouse - 8.1 miles away

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

Responds fast! Avg. 3 hours 48 minutes

$338.00

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from $338.00 / night

1 / 33

Siesta Key House - 10.2 miles away

  • 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

(2)

1 / 41

Siesta Key Condo - 8.3 miles away

  • 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 / 27

Sarasota House - 7.3 miles away

  • 4
  • 11
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 2 hours 25 minutes

“It doesn't get any better! We rented the property for a week of wedding adventures and it was lovely! Low key enough, beautifully maintained, clean, fresh and beach front! Easy to hang out on the property and cook your own meals, enjoy the hammock,...”
- Review left on 01/16/2015

$516.00

Excellent (7 reviews)

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from $516.00 / night

1 / 18

Siesta Key House - 7.7 miles away

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

Responds fast! Avg. 3 hours 27 minutes

$260.00

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from $260.00 / night

(1)

1 / 76

Siesta Key House - 7.7 miles away

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

Responds fast! Avg. 3 hours 27 minutes

$280.00

Excellent (1 reviews)

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from $280.00 / night

1 / 43

Siesta Key House - 8.2 miles away

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

Responds fast! Avg. 3 hours 27 minutes

$466.00

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from $466.00 / night

1 / 16

Siesta Key House - 10.3 miles away

  • 3
  • 8
  • 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

1 / 15

Sarasota Apartment - 6.9 miles away

  • 3
  • 3
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$115.00

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from $115.00 / night

(21)

1 / 27

Sarasota Villa - 12.1 miles away

  • 2
  • 6
  • min stay varies
  • Nearest beach 3 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 26 minutes

“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

$107.00

Excellent (21 reviews)

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from $107.00 / night

1 / 15

Sarasota House - 12.5 miles away

  • 2
  • 6
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

Responds fast! Avg. 3 hours 9 minutes

$144.00

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from $144.00 / night

1 / 25

Bradenton House - 13.4 miles away

  • 4
  • 8
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$315.00

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from $315.00 / night

1 / 29

Siesta Key House - 10.2 miles away

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

Responds fast! Avg. 3 hours 27 minutes

$220.00

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from $220.00 / night

1 / 29

Siesta Key House - 7.4 miles away

  • 4
  • 13
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 45 minutes

$295.00

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from $295.00 / night