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Anna Maria Island Waterfront Vacation Rentals, Beach Rentals & More - 66 Rentals Available.

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66 Vacation rentals

Filters applied: Waterfront

(5)

1 / 26

Bradenton Beach Apartment

  • 1
  • 5
  • 2 nights min
  • Air conditioning

$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
“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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(31)

1 / 25

Anna Maria Island Cottage

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

Responds fast! Avg. 59 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

$153.00

Excellent (31 reviews)

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from $153.00 / 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 12 minutes

$230.00

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from $230.00 / night

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(1)

1 / 33

Anna Maria Island Villa

  • 2
  • 5
  • 2 nights min
  • Child friendly

$304.00

Excellent (1 reviews)

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from $304.00 / night

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(23)

1 / 44

Anna Maria Island House

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

Responds fast! Avg. 3 hours 30 minutes

“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

$343.00

Excellent (23 reviews)

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from $343.00 / 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

$459.00

Very Good (7 reviews)

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from $459.00 / night

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(2)

1 / 72

Anna Maria House

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

$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

$327.00

Very Good (2 reviews)

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from $327.00 / 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 12 minutes

$327.00

Excellent (3 reviews)

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from $327.00 / night

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(6)

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

$155.00

Excellent (6 reviews)

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from $155.00 / night

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1 / 26

Bradenton Beach Villa

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

Responds fast! Avg. 3 hours 21 minutes

$459.00

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from $459.00 / night

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Your search has been expanded 19.6 miles to include more rentals

(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 / 36

St. Petersburg House - 17.9 miles away

  • 4
  • 10
  • 3 nights min
  • Child friendly
  • Air conditioning

$1,374.00

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from $1,374.00 / night

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1 / 24

St. Petersburg Manor house - 18.9 miles away

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,374.00

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from $1,374.00 / night

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1 / 8

Sarasota Condo - 12.7 miles away

  • 1
  • 2
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 9 mi
  • Swimming pool

Responds fast! Avg. 2 hours 22 minutes

$57.00

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from $57.00 / night

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(3)

1 / 34

Bradenton Condo - 17.1 miles away

  • 2
  • 6
  • 3 nights min
  • Nearest beach 12 mi
  • Swimming pool
  • Child friendly

$144.00

Excellent (3 reviews)

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from $144.00 / night

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1 / 23

Madeira Beach Condo - 18.4 miles away

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

$172.00

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from $172.00 / night

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1 / 19

Palma Sola House - 6.7 miles away

  • 6
  • 18
  • 7 nights min
  • Child friendly

$300.00

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from $300.00 / night

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(1)

1 / 16

Bradenton House - 10.2 miles away

  • 3
  • 4
  • min stay varies
  • Nearest beach 10 mi
  • Swimming pool
  • Air conditioning

$201.00

Excellent (1 reviews)

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from $201.00 / night

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(11)

1 / 20

Bradenton House - 6.6 miles away

  • 3
  • 4
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden
“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

$287.00

Very Good (11 reviews)

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from $287.00 / night

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1 / 20

Madeira Beach Cottage - 18.7 miles away

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

$123.00

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from $123.00 / night

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(1)

1 / 26

Sarasota Cottage - 16.8 miles away

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

$149.00

Excellent (1 reviews)

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from $149.00 / night

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(8)

1 / 17

St. Petersburg Condo - 13.1 miles away

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Air conditioning
  • Pet friendly
“We thoroughly enjoyed our stay in this beautiful condo overlooking Boca Ciega Bay.. Very clean, comfortable home, what a nice view of the bay with dolphins regularly swimming by! The owner, Ken, was stellar to deal with, all our needs were totally...”
- Review left on 05/21/2016

$86.00

Excellent (8 reviews)

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from $86.00 / night

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(3)

1 / 11

Sarasota Condo - 16.8 miles away

  • 2
  • 6
  • 30 nights min
  • Nearest beach 20 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 30 minutes

“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

$115.00

Excellent (3 reviews)

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from $115.00 / night

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1 / 25

Madeira Beach Condo - 19.6 miles away

  • 1
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$131.00

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from $131.00 / night

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1 / 18

Madeira Beach House - 18.7 miles away

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

$164.00

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from $164.00 / night

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1 / 34

Madeira Beach House - 19.3 miles away

  • 3
  • 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden

$205.00

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from $205.00 / night

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(5)

1 / 13

Treasure Island Condo - 15.6 miles away

  • 1
  • 4
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

Responds fast! Avg. 1 hour 25 minutes

$109.00

Excellent (5 reviews)

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from $109.00 / night

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1 / 22

Madeira Beach Condo - 19 miles away

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

$148.00

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from $148.00 / night

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(24)

1 / 33

Madeira Beach Condo - 19 miles away

  • 2
  • 6
  • 7 nights min
  • 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

$180.00

Very Good (24 reviews)

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from $180.00 / night

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1 / 19

Madeira Beach Condo - 19 miles away

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

$148.00

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from $148.00 / night

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(1)

1 / 25

Madeira Beach Condo - 19 miles away

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

$221.00

Excellent (1 reviews)

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from $221.00 / night

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(29)

1 / 26

Treasure Island Cottage - 15 miles away

  • 1
  • 4
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
“This was such a fun cottage to stay in for the week. It was very clean, had everything that we needed, and it was close to so many fun places in Treasure Island and Madeira Beach with John's Pass. Michael and Gitta made sure that we had everything...”
- Review left on 07/13/2016

$92.00

Very Good (29 reviews)

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from $92.00 / night

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(40)

1 / 16

Sarasota Guest house - 17.5 miles away

  • 1
  • 2
  • 7 nights min
  • Swimming pool
  • Car not necessary
  • Air conditioning
“My husband and I stayed in Joyce and Jeff's beautiful guest apartment for two weeks. Everything was perfect inside and out. The property was immaculate and the owners included extra touches that went above and beyond. While we spent most of our time...”
- Review left on 08/09/2017

$180.00

Excellent (40 reviews)

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from $180.00 / night

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(1)

1 / 27

Madeira Beach Condo - 19 miles away

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

$156.00

Excellent (1 reviews)

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from $156.00 / night

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(3)

1 / 27

Madeira Beach Condo - 19 miles away

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

$180.00

Excellent (3 reviews)

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from $180.00 / night

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(20)

1 / 120

St. Petersburg Condo - 12.5 miles away

  • 2
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool

Responds fast! Avg. 1 hour 57 minutes

“We had stayed all around Florida , but Never had a view like this, water everywhere, from all the windows. When you see the pictures they are gorgeous but in real life Wow. I think this is one of the best condo's we have stayed in. The owners are...”
- Review left on 05/30/2017

$230.00

Excellent (20 reviews)

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from $230.00 / night

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(28)

1 / 20

Bradenton House - 14.5 miles away

  • 4
  • 8
  • 7 nights min
  • Nearest beach 15 mi
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 32 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 (28 reviews)

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from $150.00 / night

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(3)

1 / 5

Bradenton House - 17.2 miles away

  • 3
  • 6
  • 7 nights min
  • Nearest beach 20 mi
  • Swimming pool
  • Child friendly
“we rented this home for a week in July, the home is beautiful, it is equipped with every thing you could possibly need. the pool area was very relaxing and enjoyable. we loved the hone and would rent again...”
- Review left on 07/13/2014

$167.00

Excellent (3 reviews)

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from $167.00 / night

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