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Anna Maria Vacation Rentals & Beach Rentals with Swimming Pool - 122 Rentals Available.

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122 Vacation rentals

Filters applied: Swimming pool

(2)

1 / 72

Anna Maria House

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Air conditioning
  • Private garden

$383.00

Excellent (2 reviews)

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from $383.00 / night

1 / 26

Anna Maria House

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Pet friendly

$286.00

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from $286.00 / night

(2)

1 / 31

Anna Maria House

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

$315.00

Excellent (2 reviews)

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from $315.00 / night

(3)

1 / 35

Anna Maria House

  • 3
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$286.00

Excellent (3 reviews)

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from $286.00 / night

(1)

1 / 35

Anna Maria House

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$172.00

Excellent (1 reviews)

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from $172.00 / night

(1)

1 / 33

Anna Maria House

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$186.00

Excellent (1 reviews)

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from $186.00 / night

1 / 16

Anna Maria House

  • 3
  • 6
  • 28 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$206.00

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from $206.00 / night

Your search has been expanded 19.7 miles to include more rentals

(6)

1 / 40

Bradenton House - 17.5 miles away

  • 3
  • 6
  • min stay varies
  • Nearest beach 25 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 24 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

$111.00

Excellent (6 reviews)

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from $111.00 / night

(7)

1 / 17

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 (7 reviews)

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Pricing unknown

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 / 19

Madeira Beach Condo - 19 miles away

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

$258.00

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from $258.00 / 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 0 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)

1 / 30

St. Petersburg Condo - 12.4 miles away

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

$72.00

Excellent (1 reviews)

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from $72.00 / night

(20)

1 / 108

St. Petersburg Condo - 12.4 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

$228.00

Excellent (20 reviews)

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from $228.00 / night

(22)

1 / 15

Bradenton Condo - 15.1 miles away

  • 2
  • 6
  • 6 nights min
  • Nearest beach 8 mi
  • Swimming pool
  • Child friendly
“Anita and Joe were great hosts and wonderful people! The condo is in a secure location close to lots of entertainment, attractions, and shopping. The neighborhood was quiet and friendly with lots of exercise walkers and dog walkers. We spent most...”
- Review left on 02/02/2017

$144.00

Very Good (22 reviews)

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from $144.00 / night

(33)

1 / 16

Sarasota Guest house - 17.5 miles away

  • 1
  • 2
  • 7 nights min
  • Swimming pool
  • Car not necessary
  • Air conditioning
“My husband and I stayed in Joyce and Jeff's beautiful guest apartment for two weeks. Everything was perfect inside and out. The property was immaculate and the owners included extra touches that went above and beyond. While we spent most of our time...”
- Review left on 08/09/2017

$132.00

Excellent (33 reviews)

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from $132.00 / night

(3)

1 / 27

Madeira Beach Condo - 19 miles away

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

$152.00

Excellent (3 reviews)

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from $152.00 / night

1 / 46

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

(5)

1 / 29

Bradenton Condo - 9.1 miles away

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

Responds fast! Avg. 57 minutes

$138.00

Very Good (5 reviews)

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from $138.00 / 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

(21)

1 / 17

Holmes Beach Townhouse - 2.7 miles away

  • 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

$172.00

Very Good (21 reviews)

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from $172.00 / night

1 / 22

Madeira Beach Condo - 19 miles away

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

$148.00

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from $148.00 / 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

$207.00

Excellent (4 reviews)

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from $207.00 / night

(1)

1 / 16

Bradenton Condo - 6.2 miles away

  • 3
  • 6
  • min stay varies
  • 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 / 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

1 / 21

Bradenton Apartment - 9.3 miles away

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

Responds fast! Avg. 57 minutes

$149.00

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from $149.00 / 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

1 / 20

Bradenton Beach Condo - 4.9 miles away

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

$655.00

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from $655.00 / night

1 / 24

Bradenton Beach Condo - 4.6 miles away

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$344.00

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from $344.00 / night

1 / 12

Madeira Beach Apartment - 18 miles away

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

$315.00

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from $315.00 / night

(3)

1 / 43

Redington Beach Manor house - 19.7 miles away

  • 5
  • 13
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“This home was amazing. We brought three generations and had plenty of space--both for together times and when we wanted privacy! Three teenage girls enjoyed the privacy of the garage suite. We called it the bachelorette pad! The pool and patio area...”
- Review left on 10/22/2017

$1,145.00

Excellent (3 reviews)

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from $1,145.00 / night

(7)

1 / 28

Treasure Island Condo - 16.5 miles away

  • 2
  • 5
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 25 minutes

“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

$148.00

Very Good (7 reviews)

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from $148.00 / night

1 / 26

Bradenton Beach Villa - 3.7 miles away

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

$262.00

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from $262.00 / night

(1)

1 / 34

St. Petersburg Condo - 12.5 miles away

  • 2
  • 5
  • min stay varies
  • Nearest beach 4 mi
  • Swimming pool
  • Child friendly

$72.00

Excellent (1 reviews)

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from $72.00 / night

(1)

1 / 13

Lakewood Ranch House - 18.9 miles away

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

$279.00

Average (1 reviews)

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from $279.00 / 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 / 36

St. Petersburg Apartment - 12.6 miles away

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

$82.00

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from $82.00 / night

(22)

Certificate of Excellence

1 / 44

Anna Maria Island House - 4 miles away

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 59 minutes

Certificate of Excellence

“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

$205.00

Excellent (22 reviews)

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from $205.00 / night

1 / 8

Sarasota Condo - 12.6 miles away

  • 1
  • 2
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 9 mi
  • Swimming pool

Responds fast! Avg. 2 hours 41 minutes

$57.00

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from $57.00 / night

1 / 15

Bradenton House - 9.7 miles away

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 57 minutes

$343.00

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from $343.00 / night