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Anna Maria Island 2-bedroom Vacation Rentals, Beach Rentals & More - 50 Rentals Available.

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50 Vacation rentals

Filters applied: 2+ Bedrooms

(19)

1 / 27

Anna Maria House

  • 4
  • 10
  • Min stay varies
  • 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

$175

Very Good (19 reviews)

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from $175 / night

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(21)

1 / 11

Holmes Beach Townhouse

  • 2
  • 6
  • Min stay varies
  • 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

Very Good (21 reviews)

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from $150 / night

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(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

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1 / 34

Holmes Beach House

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

$300

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from $300 / night

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1 / 24

Bradenton Beach House

  • 6
  • 14
  • 4 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$500

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from $500 / night

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(68)

1 / 67

Bradenton Beach Cottage

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“We were suppose to go to West Palm Beach and the hurricane at that time changed our plans and we decided to look around at a place I had been to before--Anna Maria Island. We found this ad on the Sugar Shack and we were lucky it was not rented the...”
- Review left on 02/22/2017

$214

Excellent (68 reviews)

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from $214 / night

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(1)

1 / 19

Holmes Beach Cottage

  • 3
  • 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“We couldn't have asked for a better AMI rental. I've stayed at others, but have finally found one I will stay at again (and again!) Don't worry about not being directly on the beach, because you are just a few steps away! It was wonderful to have our...”
- Review left on 04/07/2016

$271

Excellent (1 reviews)

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from $271 / night

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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

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1 / 47

Bradenton Beach House

  • 11
  • 32
  • 7 nights min
  • Ask about children
  • Air conditioning

$229

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from $229 / night

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(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

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1 / 24

Holmes Beach House

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

$400

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from $400 / night

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(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

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(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

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1 / 20

Bradenton Beach Condo

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

$272

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from $272 / night

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1 / 20

Holmes Beach House

  • 5
  • 10
  • Min stay varies
  • Child friendly

$400

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from $400 / night

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(6)

1 / 41

Bradenton Beach Condo

  • 2
  • 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • 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

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(2)

1 / 25

Holmes Beach Townhouse

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

$225

Excellent (2 reviews)

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from $225 / night

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1 / 81

Anna Maria Island Condo

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

$200

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from $200 / night

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(20)

1 / 24

Anna Maria Island Cottage

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

$87

Excellent (20 reviews)

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from $87 / night

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(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

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(5)

1 / 92

Anna Maria Island Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“The unit was well equipped with a good kitchen and lots of seating. TV's where great. We have two kids so we needed a place that could work for at home cooking as well. The location was perfect for us. The balcony was a perfect place for having a...”
- Review left on 01/05/2016

$250

Very Good (5 reviews)

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from $250 / night

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1 / 21

Anna Maria Island Villa

  • 2
  • 3
  • 1 night min
  • Child friendly

$175

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from $175 / night

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1 / 32

Anna Maria Island House

  • 3
  • 10
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$291

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from $291 / night

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1 / 38

Bradenton Beach House

  • 6
  • 16
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$500

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from $500 / night

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(5)

1 / 93

Anna Maria Island House

  • 4
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“We enjoyed our stay at this property. The home is well decorated and all rooms are very spacious. The master bedroom is enormous with jacuzzi and large walk-in shower. The other bedrooms are very spacious too. Our manager resolved a few minor...”
- Review left on 08/10/2016

$350

Excellent (5 reviews)

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from $350 / night

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(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

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(4)

1 / 46

Bradenton Beach Condo

  • 2
  • 4
  • 3 nights min
  • Ask about children
  • Air conditioning
“My family and I spent a week at this beautiful place. You never need to leave the island, it has everything. Trolleys and buses, but most everything is within walking distance. There are so many things to do, swimming, shelling, fishing, bike...”
- Review left on 07/06/2012

$170

Excellent (4 reviews)

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from $170 / night

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1 / 19

Holmes Beach House

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

$199

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from $199 / night

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(3)

1 / 25

Anna Maria Island Condo

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

$143

Excellent (3 reviews)

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from $143 / night

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(1)

1 / 19

Holmes Beach Townhouse

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

$99

Excellent (1 reviews)

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from $99 / night

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(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

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(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

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(1)

1 / 47

Holmes Beach House

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • 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

$555

Excellent (1 reviews)

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from $555 / night

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(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

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(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

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1 / 24

Holmes Beach House

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

$199

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from $199 / night

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1 / 53

Holmes Beach House

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

$350

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from $350 / night

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(3)

1 / 17

Holmes Beach House

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“I like to call the Coral Cottage our own little Shangri La, at least for the two weeks we were pleased to be its residents. From the lovely landscaping to the private HEATED pool in the enclosed backyard, to the well equipped kitchen, just about...”
- Review left on 04/01/2016

$159

Excellent (3 reviews)

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from $159 / night

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(2)

1 / 20

Bradenton Beach Cottage

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

$135

Excellent (2 reviews)

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from $135 / night

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(7)

1 / 84

Anna Maria Island Condo

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
“Impeccable beach house! All the amenities one would want. Great Weber gas grill, (almost) private pool, brand new kitchen, brand new front loader washer/dryer (free). Cross the street and you're on the public beach, or drive 10 min north or south...”
- Review left on 11/23/2016

$250

Excellent (7 reviews)

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from $250 / night

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