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Anna Maria Island 2-bedroom Vacation Rentals, Beach Rentals & More - 219 Rentals Available.

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219 Vacation rentals

Filters applied: 2+ Bedrooms

1 / 32

Bradenton Beach House

  • 6
  • 13
  • min stay varies
  • Child friendly

$399.00

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from $399.00 / night

(23)

1 / 29

Anna Maria House

  • 4
  • 8
  • 28 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

Responds fast! Avg. 2 hours 3 minutes

$175.00

Very Good (23 reviews)

Book

from $175.00 / night

(5)

1 / 92

Anna Maria Island Condo

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$157.00

Very Good (5 reviews)

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from $157.00 / night

(3)

1 / 33

Bradenton Beach Cottage

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

$150.00

Very Good (3 reviews)

Book

from $150.00 / night

(1)

1 / 21

Anna Maria House

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

Responds fast! Avg. 1 hour 21 minutes

$500.00

Excellent (1 reviews)

Book

from $500.00 / night

(8)

1 / 84

Anna Maria Island Condo

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

$157.00

Excellent (8 reviews)

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from $157.00 / night

(2)

1 / 25

Holmes Beach Townhouse

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

$299.00

Excellent (2 reviews)

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from $299.00 / night

(23)

1 / 23

Anna Maria Island Cottage

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

Responds fast! Avg. 2 hours 28 minutes

$90.00

Excellent (23 reviews)

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from $90.00 / night

(16)

Certificate of Excellence

1 / 26

Anna Maria Island House

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

Responds fast! Avg. 1 hour 12 minutes

Certificate of Excellence

$450.00

Excellent (16 reviews)

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from $450.00 / night

1 / 34

Bradenton Beach Condo

  • 2
  • 6
  • min stay varies
  • Child friendly

$150.00

Book

from $150.00 / night

1 / 8

Anna Maria Island Apartment

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

$220.00

Book

from $220.00 / night

(29)

1 / 87

Bradenton Beach Condo

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$145.00

Very Good (29 reviews)

Book

from $145.00 / night

1 / 14

Anna Maria House

  • 2
  • 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly

Responds fast! Avg. 1 hour 21 minutes

$500.00

Book

from $500.00 / night

(5)

1 / 93

Anna Maria Island House

  • 4
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$360.00

Excellent (5 reviews)

Book

from $360.00 / night

1 / 53

Holmes Beach House

  • 6
  • 14
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$499.00

Book

from $499.00 / night

1 / 34

Holmes Beach House

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$399.00

Book

from $399.00 / night

1 / 70

Anna Maria Island Condo

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary

$200.00

Book

from $200.00 / night

(1)

1 / 33

Anna Maria Island Villa

  • 2
  • 3
  • min stay varies
  • Child friendly

$175.00

Excellent (1 reviews)

Book

from $175.00 / night

(6)

1 / 16

Holmes Beach Villa

  • 3
  • 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$250.00

Excellent (6 reviews)

Book

from $250.00 / night

(2)

1 / 47

Anna Maria House

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Air conditioning
  • Private garden

$334.00

Excellent (2 reviews)

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from $334.00 / night

1 / 51

Anna Maria Apartment

  • 5
  • 12
  • 4 nights min
  • Child friendly

$799.00

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from $799.00 / night

1 / 48

Anna Maria Island House

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

$130.00

Book

from $130.00 / night

1 / 81

Anna Maria Island Condo

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$165.00

Book

from $165.00 / night

(2)

1 / 19

Holmes Beach House

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

$500.00

Excellent (2 reviews)

Book

from $500.00 / night

1 / 33

Bradenton Beach House

  • 6
  • 14
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$399.00

Book

from $399.00 / night

1 / 24

Holmes Beach House

  • 4
  • 10
  • 4 nights min
  • Nearest beach 0.01 mi
  • Swimming pool
  • Child friendly

$750.00

Book

from $750.00 / night

1 / 19

Holmes Beach Townhouse

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

$199.00

Book

from $199.00 / night

1 / 45

Anna Maria Island Condo

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

$171.00

Book

from $171.00 / night

1 / 20

Bradenton Beach Condo

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

$572.00

Book

from $572.00 / night

1 / 79

Bradenton Beach Condo

  • 2
  • 6
  • min stay varies
  • Child friendly

$150.00

Book

from $150.00 / night

1 / 14

Bradenton Beach Townhouse

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

$220.00

Book

from $220.00 / night

(2)

1 / 36

Bradenton Beach Cottage

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

$150.00

Excellent (2 reviews)

Book

from $150.00 / night

(2)

1 / 20

Holmes Beach Townhouse

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

$500.00

Excellent (2 reviews)

Book

from $500.00 / night

1 / 24

Holmes Beach House

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

$700.00

Book

from $700.00 / night

(1)

1 / 8

Anna Maria Island Condo

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

$150.00

Excellent (1 reviews)

Book

from $150.00 / night

(3)

1 / 25

Anna Maria Island Condo

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

$143.00

Excellent (3 reviews)

Inquire

from $143.00 / night

1 / 19

Holmes Beach House

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

$259.00

Book

from $259.00 / night

1 / 55

Anna Maria House

  • 4
  • 8
  • 4 nights min
  • Child friendly
  • Pet friendly

Responds fast! Avg. 1 hour 21 minutes

$600.00

Book

from $600.00 / night

(21)

1 / 11

Holmes Beach Townhouse

  • 2
  • 6
  • 7 nights min
  • Nearest beach 0.05 mi
  • Swimming pool
  • Child friendly

$150.00

Very Good (21 reviews)

Book

from $150.00 / night

1 / 13

Anna Maria Island Apartment

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

$220.00

Book

from $220.00 / night