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Anna Maria 2-bedroom Vacation Rentals, Beach Rentals & More - 157 Rentals Available.

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157 Vacation rentals

Filters applied: 2+ Bedrooms

(23)

1 / 29

Anna Maria House

  • 4
  • 8
  • 28 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

Responds fast! Avg. 2 hours 3 minutes

“Whether you are a couple or three families under one roof, the layout of this home fits the bill. Three eating areas, three gathering areas plus the pool area is amazing. Newer homes on the island have five bedrooms....great...right but there is...”
- Review left on 06/25/2015

$201.00

Very Good (23 reviews)

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from $201.00 / night

(1)

1 / 21

Anna Maria House

  • 3
  • 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly

Responds fast! Avg. 1 hour 21 minutes

$573.00

Excellent (1 reviews)

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from $573.00 / night

1 / 51

Anna Maria Apartment

  • 5
  • 12
  • 4 nights min
  • Child friendly

$800.00

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from $800.00 / night

1 / 14

Anna Maria House

  • 2
  • 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly

Responds fast! Avg. 1 hour 21 minutes

$573.00

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from $573.00 / night

(2)

1 / 47

Anna Maria House

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Air conditioning
  • Private garden

Responds fast! Avg. 3 hours 22 minutes

$383.00

Excellent (2 reviews)

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from $383.00 / night

1 / 55

Anna Maria House

  • 4
  • 8
  • 4 nights min
  • Child friendly
  • Pet friendly

Responds fast! Avg. 1 hour 21 minutes

$687.00

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from $687.00 / night

Your search has been expanded 19.8 miles to include more rentals

(18)

1 / 33

St. Pete Beach Condo - 13 miles away

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

Responds fast! Avg. 2 hours 7 minutes

“The views from the patio are incredible! The sunsets are so beautiful and you can hang out and watch the dolphins go by. Only a short walk to the ocean. Paradise at St Pete Beach...”
- Review left on 03/16/2017

$187.00

Very Good (18 reviews)

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from $187.00 / night

1 / 13

Lakewood Ranch House - 18.9 miles away

  • 2
  • 4
  • 14 nights min
  • Swimming pool
  • Air conditioning
  • Private garden

$279.00

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from $279.00 / night

(1)

1 / 66

Redington Beach House - 19.8 miles away

  • 5
  • 14
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$343.00

Excellent (1 reviews)

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from $343.00 / night

(4)

1 / 19

Bradenton Villa - 17.4 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“House was a great location for our Needs. Very Clean and spacious. Heated Pool was a great asset.. Would have liked a bigger more useable grill...”
- Review left on 02/23/2017

$180.00

Excellent (4 reviews)

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from $180.00 / night

(25)

1 / 24

Bradenton House - 14.3 miles away

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

Responds fast! Avg. 1 hour 35 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 (25 reviews)

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from $150.00 / night

1 / 26

Bradenton House - 6.6 miles away

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

$158.00

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from $158.00 / night

(2)

1 / 16

Sarasota Condo - 12.6 miles away

  • 2
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool
“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 (2 reviews)

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from $114.00 / night

1 / 8

Anna Maria Island Apartment - 5 miles away

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

$252.00

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from $252.00 / night

(2)

1 / 25

Holmes Beach Townhouse - 0.1 miles away

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$299.00

Excellent (2 reviews)

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from $299.00 / night

(6)

1 / 16

Holmes Beach Villa - 2.2 miles away

  • 3
  • 6
  • 3 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

$287.00

Excellent (6 reviews)

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from $287.00 / night

(3)

1 / 16

Bradenton House - 17.1 miles away

  • 3
  • 6
  • min stay varies
  • Nearest beach 20 mi
  • Swimming pool
  • Child friendly
“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

$144.00

Excellent (3 reviews)

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from $144.00 / night

1 / 29

Cortez Townhouse - 4.8 miles away

  • 4
  • 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 22 minutes

$338.00

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from $338.00 / night

(9)

1 / 15

Madeira Beach Townhouse - 18.1 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

$118.00

Very Good (9 reviews)

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from $118.00 / night

(24)

1 / 30

Madeira Beach Condo - 19 miles away

  • 2
  • 6
  • min stay varies
  • 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

$229.00

Very Good (24 reviews)

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from $229.00 / night

1 / 18

Madeira Beach Condo - 19 miles away

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

$152.00

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from $152.00 / night

1 / 79

Bradenton Beach Condo - 4.4 miles away

  • 2
  • 6
  • min stay varies
  • Child friendly

$189.00

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from $189.00 / night

1 / 31

Siesta Key House - 19.1 miles away

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

$325.00

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from $325.00 / night

(2)

1 / 22

Longboat Key Condo - 9.8 miles away

  • 3
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
“This was a family holiday including 2 grandchildren, who loved every minute of the holiday and did not want to leave. Lovely 3 bedrooms condo in garden grounds, which lead to the beach, family swimming pool and adult pool and spa. 8 tennis courts....”
- Review left on 01/26/2017

$215.00

Very Good (2 reviews)

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from $215.00 / night

1 / 24

St. Petersburg Manor house - 18.8 miles away

  • 5
  • 15
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,145.00

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from $1,145.00 / night

1 / 28

Madeira Beach Condo - 18.3 miles away

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

Responds fast! Avg. 3 hours 30 minutes

$201.00

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from $201.00 / night

(1)

1 / 13

Madeira Beach Condo - 18.1 miles away

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

$180.00

Excellent (1 reviews)

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from $180.00 / night

(6)

1 / 12

St. Petersburg Condo - 13 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

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Excellent (6 reviews)

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Pricing unknown

1 / 17

Madeira Beach Condo - 18.3 miles away

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

Responds fast! Avg. 3 hours 30 minutes

$218.00

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from $218.00 / night

(34)

1 / 46

St. Petersburg Manor house - 16 miles away

  • 7
  • 21
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 9 mi
  • Swimming pool
“We invited our extended family to spend Christmas together this year at The Petro Mansion, hoping that the house looked as good in person as it did online. The house is just as beautiful, if not more so, in person! Alex had the house beautifully...”
- Review left on 01/02/2017

$700.00

Excellent (34 reviews)

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from $700.00 / night

1 / 12

Madeira Beach Apartment - 18 miles away

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

Responds fast! Avg. 3 hours 30 minutes

$315.00

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from $315.00 / night

1 / 20

Palma Sola House - 6.4 miles away

  • 6
  • 19
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$293.00

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from $293.00 / night

(12)

1 / 47

Treasure Island Condo - 16.8 miles away

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 34 minutes

“We enjoyed everything about Whispers. It was very clean,beautifully decorated as were all the condos each with its own theme. Ours was the Artist theme.It was very quiet, private and the heated pool and the dock were wonderful - we spent a lot of...”
- Review left on 05/05/2017

$132.00

Very Good (12 reviews)

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from $132.00 / night

(1)

1 / 13

St. Pete Beach Condo - 14.5 miles away

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$202.00

Very Good (1 reviews)

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from $202.00 / night

1 / 37

St. Petersburg Apartment - 12.5 miles away

  • 2
  • 4
  • min stay varies
  • Nearest beach 3 mi
  • Swimming pool
  • Child friendly

$72.00

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from $72.00 / night

1 / 32

St. Petersburg Apartment - 12.5 miles away

  • 2
  • 4
  • min stay varies
  • Nearest beach 3 mi
  • Swimming pool
  • Child friendly

$72.00

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from $72.00 / night

(4)

1 / 32

St. Petersburg Apartment - 12.3 miles away

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool

$85.00

Excellent (4 reviews)

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from $85.00 / night

(1)

1 / 38

St. Petersburg Apartment - 12.5 miles away

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

$82.00

Excellent (1 reviews)

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from $82.00 / night

1 / 37

St. Petersburg Condo - 12.5 miles away

  • 2
  • 4
  • min stay varies
  • Nearest beach 4 mi
  • Swimming pool
  • Child friendly

$82.00

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from $82.00 / night

1 / 34

St. Petersburg Condo - 12.3 miles away

  • 2
  • 4
  • min stay varies
  • Nearest beach 4 mi
  • Swimming pool
  • Child friendly

$85.00

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from $85.00 / night