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Anna Maria Vacation Rentals & Beach Rentals with Swimming Pool - 167 Rentals Available.

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167 Vacation rentals

Filters applied: Swimming pool

(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

“Whether you are a couple or three families under one roof, the layout of this home fits the bill. Three eating areas, three gathering areas plus the pool area is amazing. Newer homes on the island have five bedrooms....great...right but there is...”
- Review left on 06/25/2015

$201.00

Very Good (23 reviews)

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from $201.00 / night

(2)

1 / 47

Anna Maria House

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

$383.00

Excellent (2 reviews)

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from $383.00 / night

1 / 26

Anna Maria House

  • 2
  • 6
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly

$201.00

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from $201.00 / night

(1)

1 / 26

Anna Maria House

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

$315.00

Excellent (1 reviews)

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from $315.00 / night

1 / 35

Anna Maria House

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

$186.00

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from $186.00 / night

(2)

1 / 35

Anna Maria House

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

$286.00

Excellent (2 reviews)

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from $286.00 / night

1 / 35

Anna Maria House

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

$172.00

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from $172.00 / night

(1)

1 / 29

Anna Maria House

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

$215.00

Excellent (1 reviews)

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from $215.00 / night

1 / 16

Anna Maria House

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

$207.00

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from $207.00 / night

Your search has been expanded 19.2 miles to include more rentals

(2)

1 / 27

Madeira Beach Condo - 19 miles away

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

$164.00

Excellent (2 reviews)

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from $164.00 / night

1 / 13

Lakewood Ranch House - 18.9 miles away

  • 2
  • 4
  • 14 nights min
  • Swimming pool
  • Air conditioning
  • Private garden

$279.00

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from $279.00 / night

1 / 32

Bradenton Villa - 9.1 miles away

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

Responds fast! Avg. 1 hour 38 minutes

$115.00

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from $115.00 / night

1 / 53

Holmes Beach House - 2.5 miles away

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

$500.00

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from $500.00 / night

(11)

1 / 21

Madeira Beach Cottage - 18.9 miles away

  • 1
  • 4
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 2 hours 17 minutes

“i stayed in this darling cottage for nearly 4 months and it felt like home. cottage is decorated with lots of color and beachy cheer, has a little porch, private yard and cute picket fence, with parking just outside the fence and a friendly coffee...”
- Review left on 01/31/2017

$98.00

Excellent (11 reviews)

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from $98.00 / night

(2)

1 / 13

Treasure Island Condo - 15.5 miles away

  • 1
  • 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

Responds fast! Avg. 3 hours 53 minutes

$92.00

Very Good (2 reviews)

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from $92.00 / night

1 / 20

Bradenton Beach Condo - 4.9 miles away

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

$655.00

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from $655.00 / 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 / 19

Holmes Beach Townhouse - 1.1 miles away

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

$199.00

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from $199.00 / night

(24)

1 / 30

Madeira Beach Condo - 19 miles away

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Gulf front condo in Madeira Beach; location/view is outstanding and condo was fully equipped. Convenient to restaurants, shopping and attractions. Only two complaints were the carpet in unit was dirty, stained and worn and needed to be cleaned or...”
- Review left on 11/28/2016

$229.00

Very Good (24 reviews)

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from $229.00 / night

(2)

1 / 19

Holmes Beach House - 0.1 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 / 45

Anna Maria Island Condo - 2.5 miles away

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

$196.00

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from $196.00 / night

1 / 22

Madeira Beach Condo - 19 miles away

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

$129.00

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from $129.00 / night

1 / 43

Sarasota House - 19.2 miles away

  • 5
  • 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 42 minutes

$326.00

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from $326.00 / night

1 / 24

Holmes Beach House - 0.1 miles away

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

$701.00

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from $701.00 / night

(21)

1 / 11

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

$150.00

Very Good (21 reviews)

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from $150.00 / night

1 / 31

Siesta Key House - 19.1 miles away

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

Responds fast! Avg. 3 hours 42 minutes

$310.00

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from $310.00 / night

1 / 19

Holmes Beach House - 1.1 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 / 18

Madeira Beach Condo - 19 miles away

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

$213.00

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from $213.00 / night

(3)

1 / 11

Sarasota Condo - 16.7 miles away

  • 2
  • 6
  • 30 nights min
  • Nearest beach 20 mi
  • Swimming pool
  • Ask about children
“This condo was extremely well appointed and had everything that we needed. We stayed 3 months and enjoyed every minute. The owners were gracious and responsive to every question. The view was outstanding. How much did we like it -we are renting it...”
- Review left on 03/30/2015

$101.00

Excellent (3 reviews)

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from $101.00 / night

1 / 25

Bradenton House - 16.7 miles away

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

$275.00

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from $275.00 / night

1 / 26

Bradenton Beach Villa - 3.7 miles away

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

Responds fast! Avg. 1 hour 45 minutes

$262.00

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from $262.00 / night

(6)

1 / 40

Bradenton House - 17.5 miles away

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

$125.00

Excellent (6 reviews)

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from $125.00 / night

1 / 12

Madeira Beach Apartment - 18 miles away

  • 2
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$220.00

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from $220.00 / night

1 / 20

Palma Sola House - 6.4 miles away

  • 6
  • 19
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$293.00

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from $293.00 / night

1 / 21

Madeira Beach Condo - 19.1 miles away

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

$264.00

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from $264.00 / night

1 / 22

Bradenton Villa - 9.2 miles away

  • 2
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 38 minutes

$101.00

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from $101.00 / night

(1)

1 / 30

St. Petersburg Condo - 12.4 miles away

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

$70.00

Excellent (1 reviews)

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from $70.00 / 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

1 / 37

St. Petersburg Condo - 12.5 miles away

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

$80.00

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from $80.00 / night

1 / 35

St. Petersburg Condo - 12.3 miles away

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

$84.00

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from $84.00 / night