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Anna Maria Island 2-bedroom Vacation Rentals, Beach Rentals & More - 56 Rentals Available.

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56 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

Responds fast! Avg. 3 hours 14 minutes

“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

(28)

1 / 21

Anna Maria Island Cottage

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

Responds fast! Avg. 1 hour 19 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

$106.00

Excellent (28 reviews)

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from $106.00 / night

(1)

1 / 33

Anna Maria Island Villa

  • 2
  • 5
  • 2 nights min
  • Child friendly

Responds fast! Avg. 3 hours 14 minutes

$304.00

Excellent (1 reviews)

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from $304.00 / night

(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

$441.00

Excellent (23 reviews)

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from $441.00 / night

(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

$459.00

Very Good (7 reviews)

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from $459.00 / night

(2)

1 / 72

Anna Maria House

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

Responds fast! Avg. 2 hours 35 minutes

$418.00

Excellent (2 reviews)

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from $418.00 / night

(3)

1 / 36

Bradenton Beach Cottage

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

Responds fast! Avg. 3 hours 14 minutes

$327.00

Excellent (3 reviews)

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from $327.00 / night

(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

(5)

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 (5 reviews)

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from $155.00 / night

1 / 26

Bradenton Beach Villa

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

$459.00

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from $459.00 / night

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

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

(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

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

(8)

1 / 17

St. Petersburg Condo - 13.1 miles away

  • 2
  • 4
  • 2 nights min
  • 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

(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 27 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

1 / 16

Bradenton House - 10.2 miles away

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

$201.00

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from $201.00 / night

1 / 34

Madeira Beach House - 19.3 miles away

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

$164.00

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from $164.00 / night

(11)

1 / 20

Bradenton House - 6.6 miles away

  • 3
  • 6
  • 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

(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

1 / 19

Madeira Beach Condo - 19 miles away

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

$205.00

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from $205.00 / night

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

1 / 14

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

(1)

1 / 25

Madeira Beach Condo - 19 miles away

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

$344.00

Excellent (1 reviews)

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from $344.00 / night

1 / 22

Madeira Beach Condo - 19 miles away

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

$205.00

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from $205.00 / night

1 / 18

Madeira Beach House - 18.7 miles away

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

$135.00

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from $135.00 / night

(3)

1 / 27

Madeira Beach Condo - 19 miles away

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

$205.00

Excellent (3 reviews)

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from $205.00 / night

(1)

1 / 27

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

1 / 19

Palma Sola House - 6.7 miles away

  • 6
  • 18
  • 7 nights min
  • Child friendly

$300.00

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from $300.00 / night

1 / 26

Bradenton House - 6.7 miles away

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

$165.00

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from $165.00 / night

(20)

1 / 120

St. Petersburg Condo - 12.5 miles away

  • 2
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
“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

$230.00

Excellent (20 reviews)

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from $230.00 / night

(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

1 / 21

Bradenton Apartment - 9.4 miles away

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

Responds fast! Avg. 52 minutes

$148.00

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from $148.00 / night

(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

$159.00

Excellent (79 reviews)

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from $159.00 / night

(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. 2 hours 22 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

$114.00

Very Good (3 reviews)

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from $114.00 / night

(28)

1 / 21

Bradenton House - 14.5 miles away

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 15 mi
  • Swimming pool

Responds fast! Avg. 1 hour 17 minutes

“The location of this house is really outstanding. We enjoyed being on the river, watching the beautiful sunsets daily, watching birds come and go into the inlets. It is a private place within a lovely subdivision with lakes and riverfront. We also...”
- Review left on 02/02/2017

$150.00

Excellent (28 reviews)

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from $150.00 / night

(12)

1 / 23

Bradenton House - 17.6 miles away

  • 3
  • 6
  • min stay varies
  • Nearest beach 15 mi
  • Swimming pool
  • Child friendly
“My stay was from July 2- July 16 and I absolutely loved it. The rooms and bathrooms were super clean. Kitchen has all the appliances you needed it, home came with shower towels and amazing air conditioning through the vents. The neighborhood was...”
- Review left on 07/17/2016

$230.00

Excellent (12 reviews)

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from $230.00 / night

1 / 21

Madeira Beach Condo - 19.2 miles away

  • 3
  • 8
  • 5 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

$264.00

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from $264.00 / night

(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 10 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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from $115.00 / night

(10)

1 / 15

Madeira Beach Townhouse - 18.2 miles away

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