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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

(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

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(31)

1 / 25

Anna Maria Island Cottage

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

Responds fast! Avg. 2 hours 6 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

$153.00

Excellent (31 reviews)

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from $153.00 / night

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(1)

1 / 33

Anna Maria Island Villa

  • 2
  • 5
  • 2 nights min
  • Child friendly

$304.00

Excellent (1 reviews)

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from $304.00 / night

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(23)

1 / 44

Anna Maria Island House

  • 4
  • 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 30 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

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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

$458.00

Very Good (7 reviews)

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from $458.00 / night

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(2)

1 / 72

Anna Maria House

  • 2
  • 6
  • 2 nights min
  • Swimming pool
  • Air conditioning
  • Private garden

$418.00

Excellent (2 reviews)

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from $418.00 / night

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(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

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(6)

1 / 24

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

$155.00

Excellent (6 reviews)

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from $155.00 / night

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1 / 26

Bradenton Beach Villa

  • 4
  • 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 21 minutes

$458.00

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from $458.00 / night

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Your search has been expanded 19.4 miles to include more rentals

(1)

1 / 16

Bradenton Condo - 6.3 miles away

  • 3
  • 6
  • 120 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
“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

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1 / 36

St. Petersburg House - 17.9 miles away

  • 4
  • 10
  • 3 nights min
  • Child friendly
  • Air conditioning

$1,374.00

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from $1,374.00 / night

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1 / 24

St. Petersburg Manor house - 18.9 miles away

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,374.00

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from $1,374.00 / night

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(3)

1 / 34

Bradenton Condo - 17.1 miles away

  • 2
  • 6
  • 3 nights min
  • Nearest beach 12 mi
  • Swimming pool
  • Child friendly

$144.00

Excellent (3 reviews)

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from $144.00 / night

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1 / 23

Madeira Beach Condo - 18.4 miles away

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

$172.00

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from $172.00 / night

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(1)

1 / 16

Bradenton House - 10.2 miles away

  • 3
  • 4
  • min stay varies
  • Nearest beach 10 mi
  • Swimming pool
  • Air conditioning

$201.00

Excellent (1 reviews)

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from $201.00 / night

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(11)

1 / 20

Bradenton House - 6.6 miles away

  • 3
  • 4
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden
“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

$287.00

Very Good (11 reviews)

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from $287.00 / night

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1 / 20

Madeira Beach Cottage - 18.7 miles away

  • 2
  • 4
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

$123.00

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from $123.00 / night

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(8)

1 / 17

St. Petersburg Condo - 13.1 miles away

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Air conditioning
  • Pet friendly
“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

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(3)

1 / 11

Sarasota Condo - 16.8 miles away

  • 2
  • 6
  • 30 nights min
  • Nearest beach 20 mi
  • Swimming pool
  • Child friendly

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

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1 / 18

Madeira Beach House - 18.7 miles away

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

$164.00

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1 / 34

Madeira Beach House - 19.3 miles away

  • 3
  • 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden

$205.00

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1 / 22

Madeira Beach Condo - 19 miles away

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

$148.00

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(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

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1 / 19

Madeira Beach Condo - 19 miles away

  • 2
  • 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$148.00

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(1)

1 / 25

Madeira Beach Condo - 19 miles away

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

$221.00

Excellent (1 reviews)

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from $221.00 / night

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(1)

1 / 27

Madeira Beach Condo - 19 miles away

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

$156.00

Excellent (1 reviews)

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(3)

1 / 27

Madeira Beach Condo - 19 miles away

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

$180.00

Excellent (3 reviews)

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from $180.00 / night

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(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

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(25)

1 / 28

St. Pete Beach Condo - 13.1 miles away

  • 2
  • 5
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 1 hour 58 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

$241.00

Excellent (25 reviews)

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from $241.00 / night

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(20)

1 / 50

Treasure Island Condo - 15.6 miles away

  • 2
  • 5
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

Responds fast! Avg. 1 hour 28 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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(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

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(10)

1 / 15

Madeira Beach Townhouse - 18.2 miles away

  • 2
  • 4
  • 7 nights min
  • Nearest beach 30 mi
  • Swimming pool
  • Child friendly

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

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(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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(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

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(5)

1 / 29

Bradenton Condo - 9.1 miles away

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

$138.00

Very Good (5 reviews)

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from $138.00 / night

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(79)

1 / 26

Treasure Island Condo - 15.4 miles away

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“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

$169.00

Excellent (79 reviews)

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(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

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1 / 24

Bradenton Villa - 9.3 miles away

  • 2
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$138.00

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1 / 32

Bradenton Villa - 9.2 miles away

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

$132.00

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from $132.00 / night

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1 / 30

Bradenton Villa - 9.2 miles away

  • 2
  • 7
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$138.00

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from $138.00 / night

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