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Longboat Key 2-bedroom Vacation Rentals, Apartments & More - 369 Rentals Available.

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369 Vacation rentals

Filters applied: 2+ Bedrooms

1 / 17

Longboat Key House

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

$1,260.00

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from $1,260.00 / night

(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

1 / 14

Longboat Key House

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Pet friendly

$166.00

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from $166.00 / night

1 / 20

Longboat Key Apartment

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children

$84.00

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from $84.00 / night

1 / 21

Longboat Key House

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Pet friendly

$133.00

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from $133.00 / night

1 / 24

Longboat Key House

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Ask about children
  • Pet friendly

$217.00

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from $217.00 / night

1 / 27

Longboat Key Apartment

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children

$134.00

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from $134.00 / night

1 / 28

Longboat Key Apartment

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Ask about children

$600.00

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from $600.00 / night

1 / 26

Longboat Key Condo

  • 2
  • 8
  • min stay varies
  • Swimming pool
  • Ask about children

$150.00

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from $150.00 / night

1 / 24

Longboat Key House

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Pet friendly

$150.00

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from $150.00 / night

1 / 47

Longboat Key Apartment

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children

$84.00

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from $84.00 / night

1 / 34

Longboat Key House

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Pet friendly

$166.00

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from $166.00 / night

1 / 24

Longboat Key House

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Ask about children

$500.00

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from $500.00 / night

Your search has been expanded 14.4 miles to include more rentals

(38)

1 / 24

Siesta Key Condo - 9.7 miles away

  • 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

(5)

1 / 24

Siesta Key Condo - 9.7 miles away

  • 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 (5 reviews)

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from $85.00 / night

(3)

1 / 33

Bradenton Beach Cottage - 8.4 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

$172.00

Very Good (3 reviews)

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from $172.00 / night

1 / 25

Sarasota House - 10.9 miles away

  • 3
  • 6
  • 7 nights min
  • Nearest beach 2 mi
  • Child friendly
  • Air conditioning

$197.00

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from $197.00 / 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 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

1 / 21

Sarasota House - 7.7 miles away

  • 3
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 42 minutes

$125.00

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from $125.00 / 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

(7)

1 / 55

Sarasota House - 10.9 miles away

  • 2
  • 4
  • min stay varies
  • Nearest beach 3 mi
  • Swimming pool
  • Ask about children
“This is our fourth or fifth year that we have come to the villa in December we absolutely love it . There is so much to do there are tennis courts & communal pool, there is a mall around the corner plenty of publix & a short drive to the beach. The...”
- Review left on 12/29/2016

$93.00

Very Good (7 reviews)

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from $93.00 / 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. 2 hours 28 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

(9)

1 / 24

Siesta Key Condo - 9.7 miles away

  • 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

(18)

1 / 12

Bradenton House - 14.4 miles away

  • 4
  • 8
  • 7 nights min
  • 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

(11)

1 / 20

Bradenton House - 7.7 miles away

  • 3
  • 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
“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

$164.00

Very Good (11 reviews)

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from $164.00 / night

(6)

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

Excellent (6 reviews)

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from $287.00 / night

1 / 27

Siesta Key House - 11.2 miles away

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 42 minutes

$150.00

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from $150.00 / night

1 / 19

Holmes Beach Townhouse - 11.8 miles away

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$199.00

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from $199.00 / night

(21)

1 / 11

Holmes Beach Townhouse - 10.1 miles away

  • 2
  • 6
  • 7 nights min
  • Nearest beach 0.05 mi
  • Swimming pool
  • Child friendly
“This was my family's first visit to Anna Maria Island and it won't be our last. We loved the beaches, restaurants, and amazing sunsets. The Gulf View Townhouse was clean and centrally located, and it was an added bonus to have a pool on the...”
- Review left on 07/19/2016

$172.00

Very Good (21 reviews)

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from $172.00 / night

(2)

1 / 19

Holmes Beach House - 12.3 miles away

  • 5
  • 12
  • min stay varies
  • Nearest beach 0.02 mi
  • Swimming pool
  • Child friendly

$500.00

Excellent (2 reviews)

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from $500.00 / night

1 / 27

Siesta Key House - 7.3 miles away

  • 4
  • 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 42 minutes

$235.00

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from $235.00 / 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. 3 hours 50 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

$567.00

Excellent (7 reviews)

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from $567.00 / 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 42 minutes

$235.00

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from $235.00 / night

1 / 14

Bradenton Beach Townhouse - 7.9 miles away

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

$252.00

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from $252.00 / night

(8)

1 / 15

Sarasota Condo - 8 miles away

  • 2
  • 6
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning
“I can't say enough good things about this property. The location was great, close to the beach and an easy walk into the village. I don't think I have ever stayed anywhere that was so clean! They have every amenity available. We stayed for an...”
- Review left on 02/25/2015

$245.00

Excellent (8 reviews)

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from $245.00 / night

(3)

1 / 25

Anna Maria Island Condo - 10 miles away

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“We had a wonderful week at the tropical sunset condo I count the days to go back with my husband and two little kids (4.5 & 1.5) We loved everything in this condo and the beach was so beautiful! We saw Manatees at the road and reel Pier and Dolphins...”
- Review left on 05/24/2016

$143.00

Excellent (3 reviews)

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from $143.00 / night

1 / 51

Siesta Key House - 10.2 miles away

  • 8
  • 24
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 42 minutes

$713.00

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from $713.00 / night

1 / 19

Holmes Beach House - 11.8 miles away

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$259.00

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from $259.00 / night

1 / 15

Sarasota House - 12.6 miles away

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

Responds fast! Avg. 2 hours 45 minutes

$144.00

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from $144.00 / 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 42 minutes

$450.00

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from $450.00 / night