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Anna Maria Island Waterfront Vacation Rentals, Beach Rentals & More - 99 Rentals Available.

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99 Vacation rentals

Filters applied: Waterfront

(5)

1 / 26

Bradenton Beach Apartment

  • 1
  • 5
  • min stay varies
  • Air conditioning

Responds fast! Avg. 3 hours 17 minutes

$338.00

Excellent (5 reviews)

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from $338.00 / night

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(3)

1 / 31

Bradenton Beach Cottage

  • 2
  • 5
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly

Responds fast! Avg. 3 hours 17 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

$189.00

Very Good (3 reviews)

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from $189.00 / night

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(28)

1 / 21

Anna Maria Island Cottage

  • 2
  • 5
  • min stay varies
  • Child friendly
  • Air conditioning
  • Private garden

Responds fast! Avg. 1 hour 9 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

$218.00

Excellent (28 reviews)

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from $218.00 / night

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1 / 19

Bradenton Beach Cottage

  • 1
  • 3
  • 2 nights min
  • Car not necessary
  • Air conditioning

Responds fast! Avg. 3 hours 17 minutes

$229.00

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from $229.00 / night

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(1)

1 / 33

Anna Maria Island Villa

  • 2
  • 5
  • 2 nights min
  • Child friendly

Responds fast! Avg. 3 hours 17 minutes

$304.00

Excellent (1 reviews)

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from $304.00 / night

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(23)

Certificate of Excellence

1 / 44

Anna Maria Island House

  • 4
  • 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 1 minutes

Travelers’ Choice award

“Gorgeous, beautiful home away from home. This home has everything you and your family will need. The granite kitchen is fully equipped and beautiful. I was able to make a full Thanksgiving dinner with everything that was supplied in the home! Our...”
- Review left on 11/30/2016

$487.00

Excellent (23 reviews)

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from $487.00 / night

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(7)

1 / 16

Holmes Beach Villa

  • 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

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(2)

1 / 72

Anna Maria House

  • 2
  • 6
  • 2 nights min
  • Swimming pool
  • Air conditioning
  • Private garden

Responds fast! Avg. 3 hours 17 minutes

$418.00

Excellent (2 reviews)

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from $418.00 / night

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(2)

1 / 31

Anna Maria Island Cottage

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

Responds fast! Avg. 3 hours 17 minutes

$189.00

Very Good (2 reviews)

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from $189.00 / night

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1 / 20

Bradenton Beach Condo

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

$655.00

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from $655.00 / night

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(3)

1 / 36

Bradenton Beach Cottage

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

Responds fast! Avg. 3 hours 17 minutes

$189.00

Excellent (3 reviews)

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from $189.00 / night

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(21)

1 / 17

Holmes Beach Townhouse

  • 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

$184.00

Very Good (21 reviews)

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from $184.00 / night

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(5)

1 / 24

Holmes Beach Condo

  • 2
  • 4
  • min stay varies
  • 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

$144.00

Excellent (5 reviews)

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from $144.00 / night

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1 / 26

Bradenton Beach Villa

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$262.00

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from $262.00 / night

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1 / 34

Anna Maria Island House

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$429.00

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from $429.00 / night

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1 / 32

Anna Maria Island House

  • 1
  • 4
  • 7 nights min
  • Child friendly
  • Air conditioning

$345.00

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from $345.00 / night

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1 / 34

Anna Maria Island House

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$373.00

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from $373.00 / night

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1 / 34

Bradenton Beach House

  • 2
  • 4
  • min stay varies
  • Child friendly
  • Air conditioning

$299.00

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from $299.00 / night

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1 / 34

Anna Maria Island House

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

$411.00

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from $411.00 / night

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1 / 31

Anna Maria Island House

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$273.00

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from $273.00 / night

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1 / 34

Bradenton Beach House

  • 2
  • 5
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$291.00

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from $291.00 / night

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1 / 33

Anna Maria Island House

  • 2
  • 6
  • 7 nights min
  • Child friendly
  • Air conditioning

$223.00

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from $223.00 / night

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1 / 34

Anna Maria Island House

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$375.00

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from $375.00 / night

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1 / 34

Anna Maria Island House

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

$650.00

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from $650.00 / night

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1 / 35

Anna Maria Island House

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$345.00

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from $345.00 / night

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1 / 35

Bradenton Beach House

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

$381.00

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from $381.00 / night

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1 / 35

Anna Maria Island House

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$377.00

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from $377.00 / night

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1 / 35

Bradenton Beach Condo

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

$260.00

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from $260.00 / night

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1 / 34

Anna Maria Island House

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$258.00

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from $258.00 / night

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1 / 33

Anna Maria Island House

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

$294.00

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from $294.00 / night

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1 / 24

Anna Maria Island House

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

$411.00

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from $411.00 / night

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1 / 32

Anna Maria Island House

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

$280.00

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from $280.00 / night

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1 / 32

Bradenton Beach House

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

$350.00

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from $350.00 / night

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Your search has been expanded 19.3 miles to include more rentals

1 / 33

Bradenton House - 8.4 miles away

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

Responds fast! Avg. 54 minutes

$138.00

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from $138.00 / night

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(1)

1 / 26

Sarasota Cottage - 16.8 miles away

  • 1
  • 3
  • 7 nights min
  • Air conditioning
  • Private garden

$116.00

Excellent (1 reviews)

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from $116.00 / night

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1 / 15

Bradenton House - 9.7 miles away

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

Responds fast! Avg. 54 minutes

$457.00

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from $457.00 / night

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(1)

1 / 16

Bradenton Condo - 6.3 miles away

  • 3
  • 6
  • 120 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
“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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1 / 9

Lakewood Ranch Cottage - 19.3 miles away

  • 1
  • 2
  • 5 nights min
  • Nearest beach 10 mi
  • Air conditioning
  • Private garden

Responds fast! Avg. 3 hours 10 minutes

$126.00

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from $126.00 / night

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(7)

1 / 15

Bradenton Apartment - 19.3 miles away

  • 1
  • 2
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Air conditioning

Responds fast! Avg. 3 hours 10 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

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1 / 8

Sarasota Condo - 12.7 miles away

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

Responds fast! Avg. 2 hours 14 minutes

$57.00

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from $57.00 / night

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