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Anna Maria Island Vacation Rentals

Anna Maria Island 2-bedroom Vacation Rentals, Beach Rentals & More - 84 Rentals Available.

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Air conditioning (29)
Balcony or terrace (6)
DVD player (9)
Dishwasher (8)
Garden (3)
Grill (27)
Heated pool (9)
High Speed Internet (29)
High chair (1)
Hot tub/Jacuzzi (1)
Private pool (5)
Swimming pool (19)
Washing machine (28)
Wi-Fi available (28)

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Condo (4)
Cottage (3)
House (19)
Townhouse (1)
Villa (3)

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84 Vacation rentals

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Filters applied: 2+ Bedrooms

Distance calculated in a straight line, road distances may differ. Confirm exact location with the property owner/manager.

1 / 31

" Fish Tales"- A two bedroom adorable cottage minutes walking to beach

Bradenton Beach Cottage

2 bedrooms 2
1 bathroom
sleeps 5 5
2 nights min

Beach/lakeside relaxation
Nearest beach 0 mi
Child friendly

Responds fast! Avg. 3 hours 17 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)

from $189.00 / night

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1 / 21

Songbird Cottage

Anna Maria Island Cottage

2 bedrooms 2
1 bathroom
sleeps 5 5
min stay varies

Child friendly
Air conditioning
Private garden

Responds fast! Avg. 1 hour 9 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

$218.00

Excellent (27 reviews)

from $218.00 / night

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1 / 33

Beach Dreams " Sweet Dreams Villa"

Anna Maria Island Villa

2 bedrooms 2
2 bathrooms
sleeps 5 5
2 nights min

Child friendly

Responds fast! Avg. 3 hours 17 minutes

$304.00

Excellent (1 reviews)

from $304.00 / night

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1 / 44

4 Bdrm, 3 Bath, Private Heated Saltwater Pool, Private Elevator, Sleeps 10!

Anna Maria Island House

4 bedrooms 4
3 bathrooms
sleeps 10 10
min stay varies

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 2 hours 1 minutes

Travelers’ Choice award

“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

$344.00

Excellent (23 reviews)

from $344.00 / night

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1 / 16

Beach House on Anna Maria Island-Rental Openings

Holmes Beach Villa

3 bedrooms 3
3 bathrooms
sleeps 6 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)

from $229.00 / night

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1 / 72

"Island Oasis" A single family North end canal home with pool

Anna Maria House

2 bedrooms 2
2 bathrooms
sleeps 6 6
2 nights min

Swimming pool
Air conditioning
Private garden

Responds fast! Avg. 3 hours 17 minutes

$383.00

Excellent (2 reviews)

from $383.00 / night

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1 / 20

Amazing Beach Front Condo-Ocean views throughout!

Bradenton Beach Condo

3 bedrooms 3
2 bathrooms
sleeps 8 8
7 nights min

Beach/lakeside relaxation
Nearest beach 0 mi
Swimming pool

$655.00

from $655.00 / night

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1 / 36

"Sea Story" A two bedroom cottage minutes walking to beach.

Bradenton Beach Cottage

2 bedrooms 2
1 bathroom
sleeps 4 4
2 nights min

Beach/lakeside relaxation
Child friendly
Air conditioning

Responds fast! Avg. 3 hours 17 minutes

$189.00

Excellent (3 reviews)

from $189.00 / night

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1 / 17

Gulf View Townhouse (Unit 2) remodeled, granite counters, new tile and carpet

Holmes Beach Townhouse

2 bedrooms 2
3 bathrooms
sleeps 6 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

$184.00

Very Good (21 reviews)

from $184.00 / night

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1 / 27

Sandy Pointe #205

Holmes Beach Condo

2 bedrooms 2
2 bathrooms
sleeps 4 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)

from $126.00 / night

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1 / 26

Family Reunion Villa on Anna Maria Island, Florida

Bradenton Beach Villa

2 bedrooms 2
2 bathrooms
sleeps 6 6
7 nights min

Swimming pool
Child friendly
Air conditioning

$262.00

from $262.00 / night

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1 / 34

4102GD-6. Modern 2 Bedroom Condo with Pool and Patio

Anna Maria Island House

2 bedrooms 2
2 bathrooms
sleeps 6 6
7 nights min

Swimming pool
Child friendly
Air conditioning

$429.00

from $429.00 / night

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1 / 34

4102GD-5. Renovated 2 Bedroom Condo with Private Pool

Anna Maria Island House

2 bedrooms 2
2 bathrooms
sleeps 6 6
7 nights min

Swimming pool
Child friendly
Air conditioning

$374.00

from $374.00 / night

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1 / 34

601GDN-203. Anna Maria Island 2 Bedroom Condo with Resort Amenities

Bradenton Beach House

2 bedrooms 2
2 bathrooms
sleeps 4 4
min stay varies

Child friendly
Air conditioning

$299.00

from $299.00 / night

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1 / 34

1304BDN-R. Anna Maria Island Retreat is a Gorgeous Two Bedroom Condo

Anna Maria Island House

2 bedrooms 2
2 bathrooms
sleeps 6 6
min stay varies

Swimming pool
Child friendly
Air conditioning

$410.00

from $410.00 / night

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1 / 31

1304BDN-6B. Gorgeous 2 Bedroom Condo on Anna Maria Island. Call for Pricing !

Anna Maria Island House

2 bedrooms 2
2 bathrooms
sleeps 6 6
7 nights min

Swimming pool
Child friendly
Air conditioning

$273.00

from $273.00 / night

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1 / 34

601GDN-ABS. Anna Maria Island 2 Bedroom Condo with Ocean View. Call for Pricing

Bradenton Beach House

2 bedrooms 2
2 bathrooms
sleeps 5 5
min stay varies

Swimming pool
Child friendly
Air conditioning

$291.00

from $291.00 / night

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1 / 33

1303GDS. Gorgeous 2 Bedroom Condo in Anna Maria Island Beach

Anna Maria Island House

2 bedrooms 2
1 bathroom
sleeps 6 6
7 nights min

Child friendly
Air conditioning

$223.00

from $223.00 / night

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1 / 34

1304BDN-2B. Anna Maria Island Gorgeous 2 Bedroom Second Floor Condo

Anna Maria Island House

2 bedrooms 2
2 bathrooms
sleeps 6 6
7 nights min

Swimming pool
Child friendly
Air conditioning

$375.00

from $375.00 / night

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1 / 34

109-6STN. Gorgeous Anna Maria Island 4 Bedroom Pool Home

Anna Maria Island House

4 bedrooms 4
3 bathrooms
sleeps 8 8
7 nights min

Swimming pool
Child friendly
Air conditioning

$650.00

from $650.00 / night

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1 / 35

1304BDN-2A. Anna Maria Island Gorgeous 2 Bedroom First Floor Condo

Anna Maria Island House

2 bedrooms 2
2 bathrooms
sleeps 6 6
7 nights min

Swimming pool
Child friendly
Air conditioning

$345.00

from $345.00 / night

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1 / 35

601GDN-101. Anna Maria Island 2 Bedroom Condo with Ocean View

Bradenton Beach House

2 bedrooms 2
2 bathrooms
sleeps 6 6
min stay varies

Child friendly
Air conditioning

$381.00

from $381.00 / night

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1 / 35

1304BDN-5B. Lovely Updated Anna Maria Condo with Bay View

Anna Maria Island House

2 bedrooms 2
2 bathrooms
sleeps 6 6
7 nights min

Swimming pool
Child friendly
Air conditioning

$377.00

from $377.00 / night

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1 / 35

601GDN-IBS. Anna Maria Island 2 Bedroom Condo with Gulf View

Bradenton Beach Condo

2 bedrooms 2
2 bathrooms
sleeps 5 5
7 nights min

Child friendly
Air conditioning

$260.00

from $260.00 / night

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1 / 34

601GDN-209. Beautiful Anna Maria Island 2 Bedroom Condo. Call for Pricing !

Anna Maria Island House

2 bedrooms 2
2 bathrooms
sleeps 6 6
7 nights min

Swimming pool
Child friendly
Air conditioning

$258.00

from $258.00 / night

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1 / 24

4501GD. Lovely 2 Bedroom Condo on Anna Marie Island. Call for Pricing !

Holmes Beach Condo

2 bedrooms 2
1 bathroom
sleeps 6 6
min stay varies

Child friendly
Air conditioning

$365.00

from $365.00 / night

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1 / 33

1304BDN-7A. Bay Area Anna Maria 2 Bedroom Condo

Anna Maria Island House

2 bedrooms 2
2 bathrooms
sleeps 6 6
min stay varies

Swimming pool
Child friendly
Air conditioning

$294.00

from $294.00 / night

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1 / 24

1203BDN. Modern 2 Bedroom Condo on Anna Marie Island

Anna Maria Island House

2 bedrooms 2
2 bathrooms
sleeps 6 6
min stay varies

Swimming pool
Child friendly
Air conditioning

$410.00

from $410.00 / night

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1 / 32

601GDN-207. Lovely Anna Maria Island 2 Bedroom Condo. Call for Pricing !

Anna Maria Island House

2 bedrooms 2
2 bathrooms
sleeps 6 6
min stay varies

Swimming pool
Child friendly
Air conditioning

$280.00

from $280.00 / night

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1 / 32

601GDN-201. Anna Maria Island 2 Bedroom Condo with Ocean View

Bradenton Beach House

2 bedrooms 2
2 bathrooms
sleeps 6 6
min stay varies

Child friendly
Air conditioning

$351.00

from $351.00 / night

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Your search has been expanded 19.3 miles to include more rentals

1 / 33

4620 enclosed lania shorewalk close to IMG and beach

Bradenton House - 8.4 miles away

3 bedrooms 3
2 bathrooms
sleeps 6 6
2 nights min

Child friendly
Air conditioning

Responds fast! Avg. 54 minutes

$138.00

from $138.00 / night

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1 / 15

LUXURY LAKEFRONT 4 BEDROOM HOUSE CLOSE TO BRADENTON BEACH AND IMG

Bradenton House - 9.7 miles away

4 bedrooms 4
3 bathrooms
sleeps 8 8
7 nights min

Swimming pool
Child friendly
Air conditioning

Responds fast! Avg. 54 minutes

$457.00

from $457.00 / night

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1 / 16

Pool & Hot Tub-Pine Bay Forest 3-Bedroom Condo, Near AMI Beaches 3 month min

Bradenton Condo - 6.3 miles away

3 bedrooms 3
2 bathrooms
sleeps 6 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)

from $107.00 / night

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1 / 36

BAY BEAUTY

St. Petersburg House - 17.9 miles away

4 bedrooms 4
3 bathrooms
sleeps 10 10
3 nights min

Child friendly
Air conditioning

$1,374.00

from $1,374.00 / night

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1 / 40

Executive Retreat Beautifully Appointed Pool Home in desirable Heritage Harbour

Bradenton House - 17.6 miles away

3 bedrooms 3
2 bathrooms
sleeps 6 6
30 nights min

Nearest beach 25 mi
Swimming pool
Child friendly

Responds fast! Avg. 53 minutes

“As soon as I unlocked the door to this property and looked in, I turned to my wife and said, "you're definitely going to be impressed" and needless to say she was!The home was by far the best we ever rented and I would have even rated it higher than...”

- Review left on 06/17/2016

$100.00

Excellent (6 reviews)

from $100.00 / night

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1 / 24

SUNSHINE HOLIDAY

St. Petersburg Manor house - 18.9 miles away

5 bedrooms 5
6 bathrooms
sleeps 10 10
min stay varies

Swimming pool
Child friendly
Air conditioning

$1,145.00

from $1,145.00 / night

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1 / 20

Starfish Cottages One Bedroom

Madeira Beach Cottage - 18.7 miles away

2 bedrooms 2
1 bathroom
sleeps 4 4
7 nights min

Child friendly
Air conditioning
Pet friendly

$99.00

from $99.00 / night

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1 / 34

Tropical Palms Duplex

Madeira Beach House - 19.3 miles away

3 bedrooms 3
2 bathrooms
sleeps 8 8
7 nights min

Child friendly
Air conditioning
Private garden

$131.00

from $131.00 / night

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1 / 33

Kima 503 Madeira Beach Front 2bd/2bath Condo Top Floor WHITE SANDY BEACHES!

Madeira Beach Condo - 19 miles away

2 bedrooms 2
2 bathrooms
sleeps 6 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

$152.00

Very Good (24 reviews)

from $152.00 / night

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1 / 16

IMG golf private 3 bed home

Bradenton House - 10.2 miles away

3 bedrooms 3
2 bathrooms
sleeps 4 4
min stay varies

Nearest beach 10 mi
Swimming pool
Air conditioning

$189.00

from $189.00 / night

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Page 1 of 3

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Anna Maria
Bradenton Beach
Holmes Beach

This is the estimated nightly price based on a weekly stay. Contact the advertiser to confirm the price - it varies depending on when you stay and how long for.

This is the estimated nightly price based on a weekly stay.

Estimated price per night based on a weekly stay. Owner fees of {FEE} per stay may apply.

This is the total cost of the stay for the dates and number of guests that you entered.

This price is an estimate based on the latest rate information available to us. Contact the advertiser to ask for the exact price, including any additional fees.

Rates for this rental are unknown, please contact the homeowner to confirm the rate.

What is Travelers’ Choice award?

Tripadvisor gives a Travelers’ Choice award to accommodations, attractions and restaurants that consistently earn great reviews from travellers and are ranked within the top 10% of properties on Tripadvisor.

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