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Anna Maria Island Vacation Rentals & Beach Rentals with Swimming Pool - 80 Rentals Available.

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80 Vacation rentals

Filters applied: Swimming pool

(23)

Certificate of Excellence

1 / 44

Anna Maria Island House

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

Responds fast! Avg. 2 hours 5 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

$344.00

Excellent (23 reviews)

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from $344.00 / 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

$229.00

Very Good (7 reviews)

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from $229.00 / night

(2)

1 / 72

Anna Maria House

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

Responds fast! Avg. 3 hours 48 minutes

$383.00

Excellent (2 reviews)

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from $383.00 / night

1 / 20

Bradenton Beach Condo

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

$655.00

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from $655.00 / 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

$184.00

Very Good (21 reviews)

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from $184.00 / night

1 / 26

Bradenton Beach Villa

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

$262.00

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from $262.00 / night

1 / 34

Anna Maria Island House

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

$429.00

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from $429.00 / night

1 / 34

Anna Maria Island House

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

$373.00

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from $373.00 / night

1 / 34

Anna Maria Island House

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

$410.00

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from $410.00 / night

1 / 31

Anna Maria Island House

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

$273.00

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from $273.00 / night

1 / 34

Bradenton Beach House

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

$291.00

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from $291.00 / night

1 / 34

Anna Maria Island House

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

$375.00

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from $375.00 / night

1 / 34

Anna Maria Island House

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$650.00

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from $650.00 / night

1 / 35

Anna Maria Island House

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

$345.00

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from $345.00 / night

1 / 35

Anna Maria Island House

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

$377.00

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from $377.00 / night

1 / 34

Anna Maria Island House

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

$258.00

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from $258.00 / night

1 / 33

Anna Maria Island House

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

$294.00

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from $294.00 / night

1 / 24

Anna Maria Island House

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

$410.00

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from $410.00 / night

1 / 32

Anna Maria Island House

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

$280.00

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from $280.00 / night

Your search has been expanded 19.6 miles to include more rentals

(12)

1 / 23

Bradenton House - 16.9 miles away

  • 3
  • 6
  • 14 nights min
  • Beach/lakeside relaxation
  • 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

$279.00

Excellent (12 reviews)

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from $279.00 / night

(1)

1 / 13

Lakewood Ranch House - 19 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 / 15

Bradenton House - 9.7 miles away

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 54 minutes

$457.00

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from $457.00 / 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

Responds fast! Avg. 2 hours 14 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

$228.00

Excellent (20 reviews)

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from $228.00 / night

(6)

1 / 40

Bradenton House - 17.6 miles away

  • 3
  • 6
  • 30 nights min
  • Nearest beach 25 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 27 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)

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from $100.00 / night

1 / 24

St. Petersburg Manor house - 18.9 miles away

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,145.00

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from $1,145.00 / night

(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 / 20

Madeira Beach Condo - 18.1 miles away

  • 1
  • 3
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 52 minutes

$126.00

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from $126.00 / night

(22)

1 / 15

Bradenton Condo - 15.3 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

(3)

1 / 11

Sarasota Condo - 16.8 miles away

  • 2
  • 6
  • 30 nights min
  • Nearest beach 20 mi
  • Swimming pool
  • Ask about children

Responds fast! Avg. 3 hours 17 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

$104.00

Excellent (3 reviews)

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from $104.00 / night

(5)

1 / 29

Bradenton Condo - 9.1 miles away

  • 2
  • 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

Responds fast! Avg. 54 minutes

$138.00

Very Good (5 reviews)

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from $138.00 / 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 / 26

Bradenton House - 6.7 miles away

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

$165.00

Inquire

from $165.00 / night

(4)

1 / 19

Bradenton Villa - 17.6 miles away

  • 3
  • 6
  • 14 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

$161.00

Excellent (4 reviews)

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from $161.00 / night

(34)

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

$131.00

Excellent (34 reviews)

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from $131.00 / 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

$172.00

Very Good (4 reviews)

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from $172.00 / night

1 / 14

Madeira Beach Condo - 18.4 miles away

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

$229.00

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from $229.00 / night

1 / 25

Madeira Beach Condo - 19.6 miles away

  • 1
  • 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

$95.00

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from $95.00 / 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

(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

$152.00

Very Good (24 reviews)

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from $152.00 / night

(7)

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 (7 reviews)

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from $86.00 / night