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Anna Maria Vacation Rentals & Beach Rentals with Swimming Pool - 130 Rentals Available.

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130 Vacation rentals

Filters applied: Swimming pool

(23)

1 / 49

Anna Maria House

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

Responds fast! Avg. 2 hours 32 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

(2)

1 / 47

Anna Maria House

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

Responds fast! Avg. 2 hours 54 minutes

$383.00

Excellent (2 reviews)

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from $383.00 / night

Your search has been expanded 19.4 miles to include more rentals

(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

(9)

1 / 13

Ellenton House - 15.3 miles away

  • 2
  • 4
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning

Responds fast! Avg. 3 hours 54 minutes

“Lovely house great setting 5 minute walk to the pool. Quiet complex friendly people. 5 minute drive to 301 for start of shops k Mart, Public, Brand name outlets and Wal-Mart, Post Office and Banks. Many restaurants on door step too. Beach approx 40...”
- Review left on 11/11/2016

$115.00

Excellent (9 reviews)

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from $115.00 / 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 39 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

(10)

1 / 8

Madeira Beach Cottage - 18.9 miles away

  • 1
  • 2
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Car not necessary

Responds fast! Avg. 35 minutes

“Newly renovated with one bedroom queen and two sleepers. One bath and fully equipped kitchen. No dishwasher and on site laundry is very clean. Direct beach access and trolley stopsl Very well maintained private pool. BBQ grill area very clean. We...”
- Review left on 08/30/2016

$115.00

Very Good (10 reviews)

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from $115.00 / 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

(18)

1 / 12

Bradenton House - 17.1 miles away

  • 4
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Superbly equipped villa in a great location. Immaculately clean with high spec kitchen which was equipped extremely well with good quality appliances. Pool area nice with fab spa overlooking lake and big outside dining area which was used all the...”
- Review left on 08/07/2016

$279.00

Excellent (18 reviews)

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from $279.00 / night

(18)

1 / 50

Treasure Island Condo - 15.5 miles away

  • 2
  • 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

Responds fast! Avg. 3 hours 6 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

$110.00

Excellent (18 reviews)

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from $110.00 / night

(12)

1 / 21

Madeira Beach Cottage - 18.9 miles away

  • 1
  • 4
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 2 hours 18 minutes

“i stayed in this darling cottage for nearly 4 months and it felt like home. cottage is decorated with lots of color and beachy cheer, has a little porch, private yard and cute picket fence, with parking just outside the fence and a friendly coffee...”
- Review left on 01/31/2017

$98.00

Excellent (12 reviews)

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from $98.00 / night

(5)

1 / 24

Bradenton Cottage - 12.2 miles away

  • 1
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“While visiting my youngest daughter in Bradenton I booked a week stay at Arbor Terrance in one of their one bedroom cottage. The one bedroom cottage was very nice, well maintained and conveniently located to shopping centers and points of interest...”
- Review left on 10/16/2015

$101.00

Excellent (5 reviews)

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from $101.00 / night

(2)

1 / 13

Treasure Island Condo - 15.5 miles away

  • 1
  • 4
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

Responds fast! Avg. 3 hours 6 minutes

$92.00

Very Good (2 reviews)

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from $92.00 / night

(4)

1 / 14

Madeira Beach Condo - 19.3 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

$148.00

Very Good (4 reviews)

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from $148.00 / night

(2)

1 / 34

Bradenton Condo - 17 miles away

  • 2
  • 6
  • min stay varies
  • Nearest beach 12 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 9 minutes

$144.00

Excellent (2 reviews)

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from $144.00 / night

(60)

1 / 28

Treasure Island Condo - 15.3 miles away

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

$144.00

Excellent (60 reviews)

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from $144.00 / night

1 / 27

Madeira Beach Condo - 19 miles away

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

$164.00

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from $164.00 / night

(3)

1 / 16

Bradenton House - 17.1 miles away

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

Responds fast! Avg. 3 hours 50 minutes

“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

(27)

1 / 11

Bradenton House - 17.2 miles away

  • 4
  • 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“The home was a great place for our group to stay. It was clean and well maintained. The location was ideal, close to golf courses and shopping and many good restaurants. We would definitely stay there again. The owner, Larry was very good to work...”
- Review left on 02/01/2017

$210.00

Excellent (27 reviews)

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from $210.00 / night

1 / 22

Madeira Beach Condo - 19 miles away

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

$152.00

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from $152.00 / 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

(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

(3)

1 / 25

Anna Maria Island Condo - 2.9 miles away

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“We had a wonderful week at the tropical sunset condo I count the days to go back with my husband and two little kids (4.5 & 1.5) We loved everything in this condo and the beach was so beautiful! We saw Manatees at the road and reel Pier and Dolphins...”
- Review left on 05/24/2016

$200.00

Excellent (3 reviews)

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from $200.00 / night

(6)

1 / 40

Bradenton House - 17.5 miles away

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

$137.00

Excellent (6 reviews)

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from $137.00 / night

1 / 15

Sarasota Apartment - 16.2 miles away

  • 3
  • 3
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$115.00

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from $115.00 / night

(15)

1 / 19

Sarasota House - 13.8 miles away

  • 3
  • 5
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“I have been traveling for a long time and stayed in many Hotels but there is nothing like staying in this home. The owner Jaye has made this place so much like home. There was every possible amenity you could think of. She did not leave any stone...”
- Review left on 05/09/2016

$126.00

Excellent (15 reviews)

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from $126.00 / night

(7)

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 (7 reviews)

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Pricing unknown

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 / 20

Madeira Beach Condo - 18.1 miles away

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

$126.00

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from $126.00 / night

1 / 42

Madeira Beach Apartment - 18 miles away

  • 2
  • 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 30 minutes

$229.00

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from $229.00 / night

1 / 15

Madeira Beach Condo - 19.4 miles away

  • 2
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$287.00

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from $287.00 / 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 / 34

St. Petersburg Condo - 12.3 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)

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

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

(1)

1 / 33

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)

1 / 36

St. Petersburg Apartment - 12.6 miles away

  • 2
  • 6
  • 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)

1 / 38

St. Petersburg Apartment - 12.3 miles away

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

$85.00

Excellent (1 reviews)

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from $85.00 / 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 / 25

St. Petersburg Apartment - 12.4 miles away

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

$114.00

Excellent (1 reviews)

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from $114.00 / 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