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Anna Maria Island 2-bedroom Vacation Rentals, Beach Rentals & More - 43 Rentals Available.

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43 Vacation rentals

Filters applied: 2 Bedrooms

(1)

1 / 20

Bradenton Beach Cottage

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

$151

Very Good (1 reviews)

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from $151 / 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

$143

Excellent (3 reviews)

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from $143 / 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

$144

Excellent (1 reviews)

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from $144 / night

1 / 70

Anna Maria Island Condo

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

from $215 / 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

$151

Very Good (20 reviews)

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from $151 / 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

(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

$151

Excellent (1 reviews)

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from $151 / 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

$160

Very Good (2 reviews)

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from $160 / night

1 / 28

Bradenton Beach Condo

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

from $115 / 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

$187

Excellent (17 reviews)

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from $187 / 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

$151

Excellent (6 reviews)

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from $151 / night

(1)

1 / 20

Bradenton Beach Cottage

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

$136

Excellent (1 reviews)

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from $136 / 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

$251

Very Good (28 reviews)

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from $251 / night

1 / 81

Anna Maria Island Condo

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

from $200 / night

(16)

1 / 24

Anna Maria Island Cottage

  • 2
  • 5
  • 7 nights min
  • Child friendly
  • Air conditioning
“We had a great time at this beautiful cottage Everything was so clean and most comfortable.Joel the owner was great to work with and very helpful.The house is so central for the beach,restaurants and amenities.We cycled on the bikes that are there...”
- Review left on 09/25/2016

$93

Excellent (16 reviews)

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from $93 / night

(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

$200

Excellent (3 reviews)

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from $200 / night

(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

$200

Very Good (5 reviews)

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from $200 / night

(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

$171

Excellent (4 reviews)

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from $171 / night

1 / 14

Anna Maria House

  • 2
  • 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly

$500

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from $500 / night

(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

$251

Excellent (7 reviews)

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from $251 / night

(7)

1 / 72

Anna Maria Island Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Hidden Oasis is a lovely property - nicely decorated, very clean, very well-kept, and equipped with pretty much everything you might need or want. It also has a fantastic view of the gulf and the beach; and this view is visible from the living room...”
- Review left on 03/16/2017

$251

Excellent (7 reviews)

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from $251 / night

(1)

1 / 47

Anna Maria House

  • 2
  • 4
  • 1 night min
  • Swimming pool
  • Air conditioning
  • Private garden

$335

Excellent (1 reviews)

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from $335 / 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 / 20

Bradenton Beach Condo

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

$344

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from $344 / night

1 / 19

Holmes Beach House

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

from $200 / 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

$251

Excellent (2 reviews)

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from $251 / night

1 / 19

Holmes Beach Townhouse

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

from $200 / 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

(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

(4)

1 / 30

Anna Maria Island House

  • 3
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“This home is exactly as pictured and the owners are so great to work with! We loved all the accommodations of the home and it was very, very clean and well maintained! It had everything we needed to enjoy both the pool and the beach. With 3...”
- Review left on 11/07/2016

$215

Excellent (4 reviews)

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from $215 / night

(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

$144

Excellent (1 reviews)

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from $144 / night

(67)

1 / 67

Bradenton Beach Cottage

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“We had a girlfriends getaway and stayed at the Sugar Shack; our second time to stay. Sheila has made great updates to the Sugar Shack, the bathrooms have been remodeled, the kitchen has been updated, the third bedroom has been remodeled and the...”
- Review left on 11/23/2014

$215

Excellent (67 reviews)

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from $215 / night

(5)

1 / 16

Holmes Beach Villa

  • 3
  • 16
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“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

$300

Excellent (5 reviews)

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from $300 / night

1 / 32

Anna Maria Island House

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

from $292 / 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

(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

$391

Excellent (5 reviews)

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from $391 / night

1 / 70

Anna Maria House

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

from $351 / night

1 / 24

Holmes Beach House

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

from $400 / 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