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Anna Maria Island Waterfront Vacation Rentals, Beach Rentals & More - 37 Rentals Available.

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37 Vacation rentals

Filters applied: Waterfront

(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

(31)

1 / 24

Anna Maria Island Cottage

  • 2
  • 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 51 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

$102.00

Excellent (31 reviews)

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from $102.00 / night

(23)

1 / 44

Anna Maria Island House

  • 4
  • 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 19 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

(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

$458.00

Very Good (7 reviews)

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from $458.00 / night

(2)

1 / 72

Anna Maria House

  • 2
  • 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning

$418.00

Excellent (2 reviews)

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from $418.00 / night

(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

(3)

1 / 36

Bradenton Beach Cottage

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

$327.00

Excellent (3 reviews)

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from $327.00 / night

(6)

1 / 24

Holmes Beach Condo

  • 2
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • 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

1 / 26

Bradenton Beach Villa

  • 4
  • 12
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$458.00

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from $458.00 / night

Your search has been expanded 19.4 miles to include more rentals

(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

$229.00

Excellent (20 reviews)

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from $229.00 / night

(1)

1 / 16

Bradenton Condo - 6.3 miles away

  • 3
  • 6
  • 120 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
“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

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. 3 hours 43 minutes

$57.00

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from $57.00 / night

(1)

1 / 24

St. Petersburg Manor house - 18.9 miles away

  • 5
  • 10
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$1,718.00

Excellent (1 reviews)

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from $1,718.00 / night

(1)

1 / 26

Sarasota Cottage - 16.8 miles away

  • 1
  • 3
  • 7 nights min
  • Beach/lakeside relaxation
  • Air conditioning
  • Private garden

$149.00

Excellent (1 reviews)

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from $149.00 / night

(3)

1 / 11

Sarasota Condo - 16.8 miles away

  • 2
  • 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 20 mi
  • Swimming pool

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

(8)

1 / 17

St. Petersburg Condo - 13.1 miles away

  • 2
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning
“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

(20)

1 / 50

Treasure Island Condo - 15.6 miles away

  • 2
  • 5
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 2 hours 15 minutes

“We absolutely loved our stay at sunset cove. The condo is very clean and has everything you could possibly need. Plenty of room for 2 adults and 2 teen girls. The location is great very close to restaurants and activities. We will definitely be...”
- Review left on 01/09/2017

$115.00

Excellent (20 reviews)

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from $115.00 / night

(1)

1 / 16

Bradenton House - 10.2 miles away

  • 3
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool

$201.00

Excellent (1 reviews)

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from $201.00 / night

(40)

1 / 16

Sarasota Guest house - 17.5 miles away

  • 1
  • 2
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary
“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

(4)

1 / 14

Madeira Beach Condo - 19.4 miles away

  • 2
  • 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Enjoyed the vacation. Rented 2 condos for family of10 for the week of July 4. Nice rooms, great beach, and amazing 4th of July fireworks on the beach from 8:30 until nearly 11:00. never seen fireworks like that before...”
- Review left on 07/18/2015

$201.00

Very Good (4 reviews)

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from $201.00 / night

(29)

1 / 26

Treasure Island Cottage - 15 miles away

  • 1
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“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

(3)

1 / 34

Bradenton Condo - 17.1 miles away

  • 2
  • 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 12 mi
  • Swimming pool

$144.00

Excellent (3 reviews)

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from $144.00 / night

(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

(11)

1 / 20

Bradenton House - 6.6 miles away

  • 3
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“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

$367.00

Very Good (11 reviews)

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from $367.00 / night

(7)

1 / 28

Treasure Island Condo - 16.6 miles away

  • 2
  • 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“The location is perfect! Your backyard is the bay. Morning Views are breathtaking!!!! My husband fished there every morning and every night. (condo has 3 fishing poles, a few beach chairs and towels) The beach is a short walk away. Publix is right...”
- Review left on 01/03/2017

$205.00

Very Good (7 reviews)

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from $205.00 / night

(3)

1 / 5

Bradenton House - 17.2 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 20 mi
  • Swimming pool
“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

(25)

1 / 28

St. Pete Beach Condo - 13.1 miles away

  • 2
  • 5
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

Responds fast! Avg. 1 hour 59 minutes

“Donna was so easy to work with and their condo was very nice. The king master bed was so comfortable and their bedroom dresser was big enough for all our clothes. Great TV and comfortable sofa and side chairs. Kitchen was nicely equipped with...”
- Review left on 02/17/2019

$225.00

Excellent (25 reviews)

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from $225.00 / night

(3)

1 / 16

Sarasota Condo - 12.7 miles away

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool

Responds fast! Avg. 3 hours 43 minutes

“We rented this two bedroom listed as a Condo, it is really two adjoining hotel rooms with kitchenettes. Nice accommodations, however the shower heads could be a little higher not convenient for taller people. Great view, right on Marina, close to the...”
- Review left on 01/23/2015

$171.00

Very Good (3 reviews)

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from $171.00 / night

(28)

1 / 20

Bradenton House - 14.5 miles away

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 15 mi
  • Child friendly

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

(79)

1 / 26

Treasure Island Condo - 15.4 miles away

  • 2
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“First and foremost, Nick was easily the most wonderful owner we have ever dealt with. He was quick to get back with us on any email and very pleasant. The condo is perfectly located on the beach, minutes from everything and walking distance to Caddy'...”
- Review left on 04/05/2017

$180.00

Excellent (79 reviews)

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from $180.00 / night

(2)

1 / 8

Sarasota Condo - 12.7 miles away

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

Responds fast! Avg. 3 hours 43 minutes

$63.00

Average (2 reviews)

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from $63.00 / night

(22)

1 / 31

St. Pete Beach House - 12.1 miles away

  • 1
  • 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly

Responds fast! Avg. 2 hours 45 minutes

$184.00

Excellent (22 reviews)

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from $184.00 / night

(10)

1 / 15

Madeira Beach Townhouse - 18.2 miles away

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 30 mi
  • Swimming pool

Responds fast! Avg. 2 hours 51 minutes

“I have stayed at Townhouse 343 for several years and have recommended it to several of my friends and co-workers. Neither I, nor any of my friends have ever been disappointed. The owners are hospitable and think of every detail to make your stay...”
- Review left on 10/08/2016

$140.00

Very Good (10 reviews)

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from $140.00 / night

(2)

1 / 13

Madeira Beach Condo - 18.2 miles away

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

Responds fast! Avg. 1 hour 4 minutes

$164.00

Excellent (2 reviews)

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from $164.00 / night

(1)

1 / 13

St. Pete Beach Condo - 14.6 miles away

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

$210.00

Very Good (1 reviews)

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from $210.00 / night

(11)

1 / 13

Treasure Island Condo - 17 miles away

  • 1
  • 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“Wonderful property at the Malyn. Very personable owner, attentive to all our needs. Went above and beyond to help us out of a tight situation. The unit is designed in a delightful manner, views from our sliding door was gorgeous, sunsets to die for....”
- Review left on 07/25/2016

$167.00

Excellent (11 reviews)

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from $167.00 / night

(9)

1 / 59

St. Pete Beach House - 12.1 miles away

  • 2
  • 7
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly

Responds fast! Avg. 2 hours 45 minutes

$204.00

Excellent (9 reviews)

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from $204.00 / night