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Anna Maria 2-bedroom Vacation Rentals, Beach Rentals & More - 167 Rentals Available.

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167 Vacation rentals

Filters applied: 2+ Bedrooms

(2)

1 / 72

Anna Maria House

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Air conditioning
  • Private garden

$383.00

Excellent (2 reviews)

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from $383.00 / night

1 / 19

Anna Maria House

  • 2
  • 6
  • 7 nights min
  • Ask about children
  • Ask about pets

$93.00

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from $93.00 / night

(1)

1 / 27

Anna Maria House

  • 4
  • 8
  • 7 nights min
  • Ask about children
  • Ask about pets

$244.00

Excellent (1 reviews)

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from $244.00 / night

(1)

1 / 22

Anna Maria House

  • 2
  • 4
  • 7 nights min
  • Ask about children
  • Air conditioning

$104.00

Excellent (1 reviews)

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from $104.00 / night

1 / 26

Anna Maria House

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

$286.00

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from $286.00 / night

(6)

1 / 16

Anna Maria House

  • 2
  • 4
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

$108.00

Very Good (6 reviews)

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from $108.00 / night

(2)

1 / 25

Anna Maria House

  • 2
  • 4
  • min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly

$150.00

Excellent (2 reviews)

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from $150.00 / night

1 / 24

Anna Maria House

  • 2
  • 6
  • 7 nights min
  • Ask about children
  • Ask about pets

$104.00

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from $104.00 / night

(2)

1 / 31

Anna Maria House

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

$315.00

Excellent (2 reviews)

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from $315.00 / night

1 / 38

Anna Maria House

  • 4
  • 8
  • min stay varies
  • Ask about children
  • Air conditioning
  • Ask about pets

$158.00

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from $158.00 / night

(3)

1 / 35

Anna Maria House

  • 3
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$286.00

Excellent (3 reviews)

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from $286.00 / night

1 / 29

Anna Maria House

  • 2
  • 6
  • 7 nights min
  • Ask about children
  • Ask about pets

$108.00

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from $108.00 / night

(3)

1 / 32

Anna Maria House

  • 2
  • 8
  • 7 nights min
  • Ask about children

$156.00

Very Good (3 reviews)

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from $156.00 / night

1 / 44

Anna Maria House

  • 3
  • 8
  • 7 nights min
  • Ask about children
  • Ask about pets

$186.00

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from $186.00 / night

1 / 14

Anna Maria House

  • 2
  • 4
  • 30 nights min
  • Ask about children
  • Ask about pets

$86.00

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from $86.00 / night

(1)

1 / 26

Anna Maria House

  • 2
  • 6
  • 7 nights min
  • Ask about children
  • Ask about pets

$260.00

Excellent (1 reviews)

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from $260.00 / night

1 / 13

Anna Maria House

  • 2
  • 6
  • 30 nights min
  • Ask about children
  • Ask about pets

$125.00

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from $125.00 / night

(1)

1 / 21

Anna Maria House

  • 2
  • 6
  • 7 nights min
  • Ask about children
  • Ask about pets

$150.00

Excellent (1 reviews)

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from $150.00 / night

(1)

1 / 22

Anna Maria House

  • 2
  • 4
  • 7 nights min
  • Ask about children
  • Ask about pets

$115.00

Very Good (1 reviews)

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from $115.00 / night

(5)

1 / 30

Anna Maria House

  • 2
  • 6
  • 7 nights min
  • Ask about children
  • Ask about pets

$118.00

Very Good (5 reviews)

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from $118.00 / night

(1)

1 / 19

Anna Maria House

  • 3
  • 6
  • 7 nights min
  • Ask about children
  • Ask about pets

$142.00

Average (1 reviews)

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from $142.00 / night

(1)

1 / 15

Anna Maria House

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

$108.00

Very Good (1 reviews)

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from $108.00 / night

(1)

1 / 35

Anna Maria House

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$172.00

Excellent (1 reviews)

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from $172.00 / night

(4)

1 / 23

Anna Maria House

  • 2
  • 4
  • 7 nights min
  • Ask about children
  • Ask about pets

$115.00

Excellent (4 reviews)

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from $115.00 / night

(1)

1 / 33

Anna Maria House

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

$186.00

Excellent (1 reviews)

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from $186.00 / night

1 / 16

Anna Maria House

  • 3
  • 6
  • 28 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$206.00

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from $206.00 / night

(1)

1 / 24

Anna Maria House

  • 2
  • 4
  • min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly

$150.00

Very Good (1 reviews)

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from $150.00 / night

(2)

1 / 26

Anna Maria House

  • 2
  • 4
  • 7 nights min
  • Ask about children
  • Ask about pets

$115.00

Excellent (2 reviews)

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from $115.00 / night

1 / 10

Anna Maria House

  • 3
  • 6
  • 30 nights min
  • Ask about children
  • Ask about pets

$150.00

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from $150.00 / night

1 / 13

Anna Maria House

  • 3
  • 8
  • min stay varies
  • Ask about children
  • Ask about pets

$236.00

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from $236.00 / night

1 / 40

Anna Maria House

  • 3
  • 8
  • min stay varies
  • Child friendly

$258.00

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from $258.00 / night

1 / 24

Anna Maria House

  • 3
  • 6
  • 28 nights min
  • Ask about children
  • Ask about pets

$136.00

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from $136.00 / night

Your search has been expanded 19 miles to include more rentals

(3)

1 / 33

Bradenton Beach Cottage - 4.5 miles away

  • 2
  • 5
  • 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

$189.00

Very Good (3 reviews)

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from $189.00 / night

1 / 37

St. Petersburg Apartment - 12.5 miles away

  • 2
  • 4
  • min stay varies
  • Nearest beach 3 mi
  • Swimming pool
  • Child friendly

$72.00

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from $72.00 / night

(6)

1 / 40

Bradenton House - 17.5 miles away

  • 3
  • 6
  • min stay varies
  • Nearest beach 25 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 24 minutes

“As soon as I unlocked the door to this property and looked in, I turned to my wife and said, "you're definitely going to be impressed" and needless to say she was!The home was by far the best we ever rented and I would have even rated it higher than...”
- Review left on 06/17/2016

$110.00

Excellent (6 reviews)

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from $110.00 / night

1 / 34

St. Petersburg Condo - 12.3 miles away

  • 2
  • 4
  • min stay varies
  • Nearest beach 4 mi
  • Swimming pool
  • Child friendly

$82.00

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from $82.00 / night

(21)

1 / 17

Holmes Beach Townhouse - 2.7 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

1 / 19

Madeira Beach Condo - 19 miles away

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

$258.00

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from $258.00 / night

1 / 14

Madeira Beach Condo - 18.3 miles away

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

$172.00

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from $172.00 / night

1 / 19

Palma Sola House - 6.6 miles away

  • 6
  • 18
  • 7 nights min
  • Child friendly

$293.00

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from $293.00 / night