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Anna Maria Island 2-bedroom Vacation Rentals, Beach Rentals & More - 127 Rentals Available.

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127 Vacation rentals

Filters applied: 2+ Bedrooms

(3)

1 / 25

Bradenton Beach Cottage

  • 2
  • 5
  • min stay varies
  • 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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(5)

1 / 125

Anna Maria Island Condo

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 50 minutes

“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

$344.00

Very Good (5 reviews)

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from $344.00 / night

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(25)

1 / 21

Anna Maria Island Cottage

  • 2
  • 5
  • min stay varies
  • Child friendly
  • Air conditioning
  • Private garden

Responds fast! Avg. 1 hour 23 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

$131.00

Excellent (25 reviews)

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from $131.00 / night

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(8)

1 / 84

Anna Maria Island Condo

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

Responds fast! Avg. 3 hours 50 minutes

“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

$458.00

Excellent (8 reviews)

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from $458.00 / night

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(5)

1 / 93

Anna Maria Island House

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 50 minutes

“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

$516.00

Excellent (5 reviews)

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from $516.00 / night

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(29)

1 / 98

Bradenton Beach Condo

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 50 minutes

“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

$344.00

Very Good (29 reviews)

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from $344.00 / night

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(23)

Certificate of Excellence

1 / 44

Anna Maria Island House

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 12 minutes

Certificate of Excellence

“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

$263.00

Excellent (23 reviews)

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from $263.00 / night

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(1)

1 / 33

Anna Maria Island Villa

  • 2
  • 5
  • min stay varies
  • Child friendly

$304.00

Excellent (1 reviews)

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from $304.00 / night

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1 / 34

Bradenton Beach Condo

  • 2
  • 6
  • 7 nights min
  • Child friendly

Responds fast! Avg. 3 hours 50 minutes

$396.00

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from $396.00 / night

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(2)

1 / 72

Anna Maria House

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Air conditioning
  • Private garden

$383.00

Excellent (2 reviews)

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from $383.00 / night

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1 / 70

Anna Maria Island Condo

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary

Responds fast! Avg. 3 hours 50 minutes

$344.00

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from $344.00 / night

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1 / 48

Anna Maria Island House

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

Responds fast! Avg. 3 hours 50 minutes

$344.00

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from $344.00 / 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

$229.00

Very Good (7 reviews)

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from $229.00 / night

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1 / 45

Anna Maria Island Condo

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

Responds fast! Avg. 3 hours 50 minutes

$344.00

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from $344.00 / night

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(2)

1 / 8

Anna Maria Island Condo

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

Responds fast! Avg. 3 hours 50 minutes

$344.00

Excellent (2 reviews)

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from $344.00 / night

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1 / 81

Anna Maria Island Condo

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 50 minutes

$396.00

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from $396.00 / night

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1 / 20

Bradenton Beach Condo

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

$655.00

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from $655.00 / night

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1 / 79

Bradenton Beach Condo

  • 2
  • 6
  • 7 nights min
  • Child friendly

Responds fast! Avg. 3 hours 50 minutes

$344.00

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from $344.00 / night

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(21)

1 / 17

Holmes Beach Townhouse

  • 2
  • 6
  • 7 nights min
  • 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

$201.00

Very Good (21 reviews)

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from $201.00 / night

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(3)

1 / 36

Bradenton Beach Cottage

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

$189.00

Excellent (3 reviews)

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from $189.00 / night

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1 / 43

Bradenton Beach Condo

  • 2
  • 6
  • 7 nights min
  • Child friendly

Responds fast! Avg. 3 hours 50 minutes

$344.00

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from $344.00 / night

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(5)

1 / 27

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

$126.00

Excellent (5 reviews)

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from $126.00 / night

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1 / 26

Bradenton Beach Villa

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

$262.00

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from $262.00 / night

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(9)

1 / 100

Anna Maria Island Condo

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 50 minutes

“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

$401.00

Excellent (9 reviews)

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from $401.00 / night

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1 / 24

Bradenton Beach Condo

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 50 minutes

$344.00

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from $344.00 / night

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1 / 34

Anna Maria Island House

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

Responds fast! Avg. 3 hours 13 minutes

$429.00

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from $429.00 / night

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1 / 34

Anna Maria Island House

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

Responds fast! Avg. 3 hours 13 minutes

$373.00

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from $373.00 / night

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1 / 34

Bradenton Beach House

  • 2
  • 4
  • min stay varies
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 13 minutes

$299.00

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from $299.00 / night

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1 / 31

Anna Maria Island House

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

Responds fast! Avg. 3 hours 13 minutes

$273.00

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from $273.00 / night

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1 / 34

Anna Maria Island House

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

Responds fast! Avg. 3 hours 13 minutes

$410.00

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from $410.00 / night

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1 / 34

Anna Maria Island House

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

Responds fast! Avg. 3 hours 13 minutes

$293.00

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from $293.00 / night

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1 / 33

Anna Maria Island House

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

Responds fast! Avg. 3 hours 13 minutes

$223.00

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from $223.00 / night

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1 / 34

Anna Maria Island House

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 13 minutes

$650.00

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from $650.00 / night

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1 / 34

Bradenton Beach House

  • 2
  • 5
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 13 minutes

$291.00

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from $291.00 / night

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1 / 35

Anna Maria Island House

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

Responds fast! Avg. 3 hours 13 minutes

$345.00

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from $345.00 / night

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1 / 35

Anna Maria Island House

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

Responds fast! Avg. 3 hours 13 minutes

$377.00

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from $377.00 / night

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1 / 34

Anna Maria Island House

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

Responds fast! Avg. 3 hours 13 minutes

$258.00

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from $258.00 / night

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1 / 35

Bradenton Beach House

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

Responds fast! Avg. 3 hours 13 minutes

$381.00

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from $381.00 / night

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1 / 33

Anna Maria Island House

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

Responds fast! Avg. 3 hours 13 minutes

$294.00

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from $294.00 / night

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1 / 24

Holmes Beach Condo

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

Responds fast! Avg. 3 hours 13 minutes

$365.00

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from $365.00 / night

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