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Anna Maria Island 2-bedroom Vacation Rentals, Beach Rentals & More - 41 Rentals Available.

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41 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

$373.00

Very Good (3 reviews)

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from $373.00 / night

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(33)

1 / 22

Anna Maria Island Cottage

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 16 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

$147.00

Excellent (33 reviews)

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from $147.00 / night

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(1)

1 / 33

Anna Maria Island Villa

  • 2
  • 5
  • 2 nights min
  • Child friendly
  • Car not necessary

$458.00

Excellent (1 reviews)

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from $458.00 / 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
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning

$745.00

Excellent (2 reviews)

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from $745.00 / night

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(3)

1 / 36

Bradenton Beach Cottage

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

$373.00

Excellent (3 reviews)

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from $373.00 / night

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(6)

1 / 24

Holmes Beach Condo

  • 2
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • 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 / 27

Bradenton Beach Villa

  • 4
  • 12
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$458.00

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from $458.00 / night

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Your search has been expanded 19.6 miles to include more rentals

(10)

1 / 15

Madeira Beach Townhouse - 18.2 miles away

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 30 mi
  • Swimming pool

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

$164.00

Very Good (10 reviews)

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from $164.00 / night

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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

Responds fast! Avg. 3 hours 59 minutes

“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

$229.00

Very Good (4 reviews)

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from $229.00 / night

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(11)

1 / 20

Bradenton House - 6.6 miles away

  • 3
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“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

$367.00

Very Good (11 reviews)

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from $367.00 / 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 25 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

$258.00

Excellent (20 reviews)

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from $258.00 / night

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(1)

1 / 16

Bradenton Condo - 6.3 miles away

  • 3
  • 6
  • 120 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
“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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(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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from $205.00 / night

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(3)

1 / 5

Bradenton House - 17.2 miles away

  • 3
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 20 mi
  • Swimming pool
“we rented this home for a week in July, the home is beautiful, it is equipped with every thing you could possibly need. the pool area was very relaxing and enjoyable. we loved the hone and would rent again...”
- Review left on 07/13/2014

$167.00

Excellent (3 reviews)

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from $167.00 / night

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(3)

1 / 16

Sarasota Condo - 12.7 miles away

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool

Responds fast! Avg. 3 hours 28 minutes

“We rented this two bedroom listed as a Condo, it is really two adjoining hotel rooms with kitchenettes. Nice accommodations, however the shower heads could be a little higher not convenient for taller people. Great view, right on Marina, close to the...”
- Review left on 01/23/2015

$171.00

Very Good (3 reviews)

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from $171.00 / night

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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)

1 / 16

Bradenton House - 10.2 miles away

  • 3
  • 4
  • 12 nights min
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool

$201.00

Excellent (1 reviews)

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from $201.00 / night

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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. 2 hours 40 minutes

$262.00

Excellent (2 reviews)

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from $262.00 / night

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(3)

1 / 28

Bradenton Condo - 17.1 miles away

  • 2
  • 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 12 mi
  • Swimming pool

Responds fast! Avg. 3 hours 42 minutes

$144.00

Excellent (3 reviews)

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from $144.00 / night

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(1)

1 / 24

St. Petersburg Manor house - 18.9 miles away

  • 5
  • 10
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 44 minutes

$1,145.00

Excellent (1 reviews)

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from $1,145.00 / night

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1 / 21

Madeira Beach Condo - 19.2 miles away

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

$264.00

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(3)

1 / 11

Sarasota Condo - 16.8 miles away

  • 2
  • 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 20 mi
  • Swimming pool
“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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(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

$197.00

Very Good (24 reviews)

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1 / 22

Madeira Beach Condo - 19 miles away

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

$197.00

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(3)

1 / 27

Madeira Beach Condo - 19 miles away

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

$197.00

Excellent (3 reviews)

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(1)

1 / 25

Madeira Beach Condo - 19 miles away

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

$197.00

Excellent (1 reviews)

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from $197.00 / 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

$197.00

Excellent (1 reviews)

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1 / 36

St. Petersburg House - 17.9 miles away

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

Responds fast! Avg. 3 hours 44 minutes

$1,374.00

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from $1,374.00 / night

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1 / 12

Madeira Beach Apartment - 18.1 miles away

  • 2
  • 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$338.00

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1 / 23

Madeira Beach Condo - 18.4 miles away

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

$229.00

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1 / 27

Madeira Beach House - 18.7 miles away

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

$201.00

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1 / 20

Madeira Beach Cottage - 18.7 miles away

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

$131.00

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1 / 19

Madeira Beach Condo - 19 miles away

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

$254.00

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from $254.00 / night

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(25)

1 / 28

St. Pete Beach Condo - 13.1 miles away

  • 2
  • 5
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

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

$344.00

Excellent (25 reviews)

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from $344.00 / night

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(79)

1 / 41

Treasure Island Condo - 15.4 miles away

  • 2
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“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

$300.00

Excellent (79 reviews)

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from $300.00 / night

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(9)

1 / 59

St. Pete Beach House - 12.1 miles away

  • 2
  • 7
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly

$264.00

Excellent (9 reviews)

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from $264.00 / night

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1 / 42

Madeira Beach Apartment - 18.1 miles away

  • 2
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$327.00

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1 / 37

Madeira Beach Condo - 18.1 miles away

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

$135.00

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from $135.00 / night

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1 / 41

Madeira Beach Condo - 19.6 miles away

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

$118.00

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from $118.00 / night

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