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Anna Maria Island Waterfront Vacation Rentals, Beach Rentals & More - 60 Rentals Available.

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60 Vacation rentals

Filters applied: Waterfront

1 / 4

Bradenton Beach Cottage

  • 1
  • 3
  • 1 night min
  • Air conditioning

$175

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from $175 / night

1 / 21

Anna Maria House

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

$500

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from $500 / night

(1)

1 / 20

Bradenton Beach Cottage

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

$150

Very Good (1 reviews)

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from $150 / night

(18)

1 / 27

Anna Maria House

  • 4
  • 10
  • 21 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
“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

$200

Very Good (18 reviews)

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from $200 / night

(3)

1 / 25

Anna Maria Island Condo

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“We had a wonderful week at the tropical sunset condo I count the days to go back with my husband and two little kids (4.5 & 1.5) We loved everything in this condo and the beach was so beautiful! We saw Manatees at the road and reel Pier and Dolphins...”
- Review left on 05/24/2016

$142

Excellent (3 reviews)

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from $142 / night

1 / 24

Bradenton Beach House

  • 6
  • 13
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $500 / night

(5)

1 / 29

Anna Maria Island House

  • 4
  • 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“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

$390

Excellent (5 reviews)

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from $390 / night

1 / 20

Bradenton Beach Condo

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$343

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from $343 / night

(1)

1 / 13

Holmes Beach House

  • 2
  • 5
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“My boyfriend and I came to this beautiful property in the middle of October. The Weather was perfect! No rain, no humidity. I must say I really really enjoyed staying at this property. We stayed in the upper level of the duplex and it was very clean...”
- Review left on 11/28/2016

$143

Excellent (1 reviews)

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from $143 / night

(1)

1 / 44

Holmes Beach House

  • 6
  • 13
  • Min stay varies
  • Ask about children
  • Air conditioning
“We are a family of 13 and had a great Christmas holiday in this house. The location is great and the house is lovely. I would highly recommend it to anyone...”
- Review left on 01/02/2017

$500

Excellent (1 reviews)

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from $500 / night

1 / 38

Bradenton Beach House

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

from $500 / night

1 / 34

Holmes Beach House

  • 5
  • 11
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $429 / night

1 / 24

Holmes Beach House

  • 6
  • 14
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $350 / night

(2)

1 / 24

Bradenton Beach House

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“My family and friends and I rented this property to celebrate my bachelorette weekend and we picked the most perfect house possible! The layout of the house was ideal for accommodating a large number of guests in addition to providing comfortable...”
- Review left on 09/06/2016

$400

Excellent (2 reviews)

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from $400 / night

(2)

1 / 22

Anna Maria House

  • 8
  • 16
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“This house is simply amazing. There is nothing that could be improved upon. The house is gorgeous, clean, and very welcoming. The pool was the bomb as was the hot tub in the evenings! The best part of the pool is that it has all day sun which...”
- Review left on 04/22/2016

$599

Excellent (2 reviews)

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from $599 / night

(1)

1 / 24

Holmes Beach Townhouse

  • 5
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“Slept 13 comfortably. Great location and pool was a lifesaver with smaller children. I would highly recommend this property...”
- Review left on 07/21/2016

$300

Excellent (1 reviews)

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from $300 / night

(9)

1 / 22

Bradenton Beach Cottage

  • 1
  • 4
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning
“Good location. Clean, well supplied, good daily maid service. Not much area for being pet friendly for bathroom and for walking dog. Parking lot flooded with minimal rain. No overhang on porch at door or over chairs to get out of rain to even enjoy...”
- Review left on 08/08/2016

$155

Very Good (9 reviews)

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from $155 / night

1 / 19

Holmes Beach House

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $199 / night

1 / 70

Anna Maria Island Condo

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

from $214 / night

1 / 70

Anna Maria House

  • 4
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $350 / night

(2)

1 / 18

Holmes Beach House

  • 3
  • 7
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“We had a wonderful vacation. Absolutely loved this rental home. Everything you need is there. My family loved the pool and having beach chairs & sand toys on hand was an added bonus. Can't wait to book our next vacation in the same home...”
- Review left on 05/04/2016

$250

Excellent (2 reviews)

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from $250 / night

1 / 24

Holmes Beach House

  • 4
  • 11
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $400 / night

1 / 14

Bradenton Beach Townhouse

  • 2
  • 4
  • Min stay varies
  • Ask about children
  • Air conditioning

$220

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from $220 / night

(20)

1 / 11

Holmes Beach Townhouse

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“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

Very Good (20 reviews)

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from $150 / night

1 / 19

Holmes Beach Townhouse

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $199 / night

(5)

1 / 27

Holmes Beach Condo

  • 2
  • 4
  • Min stay varies
  • Ask about children
  • 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

$100

Excellent (5 reviews)

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from $100 / night

(6)

1 / 19

Holmes Beach Townhouse

  • 3
  • 8
  • 2 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
“This home is beautifully decorated and well maintained. The backyard is meticulously landscaped and provides for a private relaxing environment with a short 2 block walk to your private beach access. The owners provide lots of information on...”
- Review left on 06/29/2015

$157

Very Good (6 reviews)

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from $157 / night

(1)

1 / 44

Anna Maria Island Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“This was our first time renting, we usually stay at a hotel. The unit was exactly like the photos and clean as well. I had some trouble with the garbage disposal so I called the property management and they were very professional and offer to put...”
- Review left on 07/05/2016

$150

Excellent (1 reviews)

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from $150 / night

(1)

1 / 47

Holmes Beach House

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“As beautiful as it looks in the photos, I actually think it's better in person. I literally want to live there. The house is so spacious, features a great open floor plan for family time, and offers 4 master bedrooms, spread out on 2 floors to...”
- Review left on 04/26/2016

$600

Excellent (1 reviews)

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from $600 / night

(2)

1 / 5

Holmes Beach Condo

  • 2
  • 4
  • 14 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“It was in a great location although we had a room on the second floor and crows nest was kind of in front of us and blocked the beautiful view. If I rented there again I would want a different room. The room was nice and how nice to have a lanai...”
- Review left on 10/22/2015

$159

Very Good (2 reviews)

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from $159 / night

1 / 28

Bradenton Beach Condo

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

from $114 / night

(1)

1 / 24

Holmes Beach House

  • 4
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“We found this home clean and comfortable. All especially enjoyed the large open kitchen, dining, and family room areas. The very well-maintained pool and accessories were really appreciated, given red tide prohibited us from enjoying Holmes Beach...”
- Review left on 10/04/2016

$400

Very Good (1 reviews)

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from $400 / night

(17)

1 / 77

Anna Maria Island Cottage

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“My family and I spent a week in the cottage and surrounding Anna Maria Island.We had a very relaxing vacation by the sea and enjoyed every ammentity the cottage offered.The comforts were those of our own home. Sheila was a perfect host indeed for any...”
- Review left on 08/18/2016

$186

Excellent (17 reviews)

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from $186 / night

1 / 21

Anna Maria House

  • 5
  • 11
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly

$600

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from $600 / night

(6)

1 / 41

Bradenton Beach Condo

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“Mark, the owner, is very responsive in communications. He told us to just bring yourselves and everything is there, beach towel, beach chairs, towels, etc. Sure enough everything is there and in great condition. This condo complex has private...”
- Review left on 01/25/2016

$150

Excellent (6 reviews)

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from $150 / night

(2)

1 / 25

Holmes Beach Townhouse

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

$285

Excellent (2 reviews)

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from $285 / night

(2)

1 / 20

Holmes Beach Townhouse

  • 3
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“We enjoyed this house. It was just a short walk to the beach. It was the perfect size for our family of four. The decorations were very pretty and beachy! The pool and outside landscaping was gorgeous! It came supplied with a beach wagon which was a...”
- Review left on 04/21/2016

$236

Excellent (2 reviews)

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from $236 / night

(1)

1 / 20

Bradenton Beach Cottage

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

$135

Excellent (1 reviews)

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from $135 / night

(28)

1 / 97

Bradenton Beach Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“It was a great experience. The condo was close to perfect. It was a great spot close to the beach and many restuarants and shops. The Island was perfect with free trolly service and very clean roads and ammenities. The Ocean views and the white...”
- Review left on 06/05/2016

$250

Very Good (28 reviews)

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from $250 / night

1 / 81

Anna Maria Island Condo

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

from $200 / night