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Anna Maria Island Vacation Rentals & Beach Rentals with Swimming Pool - 148 Rentals Available.

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148 Vacation rentals

Filters applied: Swimming pool

1 / 24

Holmes Beach House

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

$249.00

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from $249.00 / night

(2)

1 / 19

Holmes Beach Townhouse

  • 3
  • 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$199.00

Excellent (2 reviews)

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from $199.00 / night

(21)

1 / 11

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

$150.00

Very Good (21 reviews)

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from $150.00 / night

(2)

1 / 46

Holmes Beach House

  • 5
  • 12
  • Min stay varies
  • Nearest beach 0.02 mi
  • Swimming pool
  • Child friendly

$399.00

Excellent (2 reviews)

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from $399.00 / night

1 / 58

Anna Maria House

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

$499.00

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from $499.00 / night

(3)

1 / 25

Anna Maria Island Condo

  • 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

$143.00

Excellent (3 reviews)

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from $143.00 / night

(6)

1 / 41

Bradenton Beach Condo

  • 2
  • 5
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Mark, the owner, is very responsive in communications. He told us to just bring yourselves and everything is there, beach towel, beach chairs, towels, etc. Sure enough everything is there and in great condition. This condo complex has private...”
- Review left on 01/25/2016

$200.00

Excellent (6 reviews)

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from $200.00 / night

(11)

1 / 26

Anna Maria Island House

  • 4
  • 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“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

$440.00

Excellent (11 reviews)

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from $440.00 / night

(1)

1 / 53

Holmes Beach House

  • 6
  • 14
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$449.00

Excellent (1 reviews)

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from $449.00 / night

1 / 34

Holmes Beach House

  • 5
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$640.00

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from $640.00 / night

(2)

1 / 25

Holmes Beach Townhouse

  • 4
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$425.00

Excellent (2 reviews)

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from $425.00 / night

(3)

1 / 24

Holmes Beach Townhouse

  • 5
  • 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Slept 13 comfortably. Great location and pool was a lifesaver with smaller children. I would highly recommend this property...”
- Review left on 07/21/2016

$399.00

Excellent (3 reviews)

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from $399.00 / night

1 / 24

Holmes Beach House

  • 4
  • 10
  • 4 nights min
  • Nearest beach 0.01 mi
  • Swimming pool
  • Child friendly

$750.00

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from $750.00 / night

1 / 24

Bradenton Beach Condo

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

$200.00

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from $200.00 / night

(2)

1 / 20

Holmes Beach Townhouse

  • 3
  • 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“We enjoyed this house. It was just a short walk to the beach. It was the perfect size for our family of four. The decorations were very pretty and beachy! The pool and outside landscaping was gorgeous! It came supplied with a beach wagon which was a...”
- Review left on 04/21/2016

$226.00

Excellent (2 reviews)

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from $226.00 / night

(2)

1 / 22

Anna Maria House

  • 8
  • 16
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“This house is simply amazing. There is nothing that could be improved upon. The house is gorgeous, clean, and very welcoming. The pool was the bomb as was the hot tub in the evenings! The best part of the pool is that it has all day sun which...”
- Review left on 04/22/2016

$799.00

Excellent (2 reviews)

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from $799.00 / night

1 / 19

Holmes Beach House

  • 3
  • 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$249.00

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from $249.00 / night

(5)

1 / 93

Anna Maria Island House

  • 4
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“We enjoyed our stay at this property. The home is well decorated and all rooms are very spacious. The master bedroom is enormous with jacuzzi and large walk-in shower. The other bedrooms are very spacious too. Our manager resolved a few minor...”
- Review left on 08/10/2016

$360.00

Excellent (5 reviews)

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from $360.00 / night

(1)

1 / 19

Holmes Beach Cottage

  • 3
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“We couldn't have asked for a better AMI rental. I've stayed at others, but have finally found one I will stay at again (and again!) Don't worry about not being directly on the beach, because you are just a few steps away! It was wonderful to have our...”
- Review left on 04/07/2016

$300.00

Excellent (1 reviews)

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from $300.00 / night

1 / 45

Anna Maria Island Condo

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

$171.00

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from $171.00 / night

(9)

1 / 100

Anna Maria Island Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Hidden Oasis is a lovely property - nicely decorated, very clean, very well-kept, and equipped with pretty much everything you might need or want. It also has a fantastic view of the gulf and the beach; and this view is visible from the living room...”
- Review left on 03/16/2017

$200.00

Excellent (9 reviews)

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from $200.00 / night

(1)

1 / 47

Anna Maria House

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

$334.00

Excellent (1 reviews)

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from $334.00 / night

(5)

1 / 17

Holmes Beach House

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“I like to call the Coral Cottage our own little Shangri La, at least for the two weeks we were pleased to be its residents. From the lovely landscaping to the private HEATED pool in the enclosed backyard, to the well equipped kitchen, just about...”
- Review left on 04/01/2016

$189.00

Excellent (5 reviews)

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from $189.00 / night

(23)

1 / 27

Anna Maria House

  • 4
  • 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
“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

$175.00

Very Good (23 reviews)

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from $175.00 / night

1 / 38

Bradenton Beach House

  • 6
  • 14
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$399.00

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from $399.00 / night

(5)

1 / 92

Anna Maria Island Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“The unit was well equipped with a good kitchen and lots of seating. TV's where great. We have two kids so we needed a place that could work for at home cooking as well. The location was perfect for us. The balcony was a perfect place for having a...”
- Review left on 01/05/2016

$157.00

Very Good (5 reviews)

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from $157.00 / night

(29)

1 / 87

Bradenton Beach Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“It was a great experience. The condo was close to perfect. It was a great spot close to the beach and many restuarants and shops. The Island was perfect with free trolly service and very clean roads and ammenities. The Ocean views and the white...”
- Review left on 06/05/2016

$175.00

Very Good (29 reviews)

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from $175.00 / night

1 / 26

Bradenton Beach Villa

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

$229.00

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from $229.00 / night

(1)

1 / 78

Anna Maria Island Condo

  • 1
  • 3
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“As this was my first time to Anna Maria I was pleasantly surprised how very nice it is. My accommodations were above what I expected. The location is perfect for going to the beach, shopping, dining, or just relaxing by the pool. I enjoyed my stay so...”
- Review left on 03/10/2015

$120.00

Excellent (1 reviews)

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from $120.00 / night

(1)

1 / 49

Holmes Beach House

  • 6
  • 12
  • Min stay varies
  • Nearest beach 0.01 mi
  • Swimming pool
  • Child friendly
“As beautiful as it looks in the photos, I actually think it's better in person. I literally want to live there. The house is so spacious, features a great open floor plan for family time, and offers 4 master bedrooms, spread out on 2 floors to...”
- Review left on 04/26/2016

$555.00

Excellent (1 reviews)

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from $555.00 / night

(2)

1 / 18

Holmes Beach House

  • 3
  • 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
“We had a wonderful vacation. Absolutely loved this rental home. Everything you need is there. My family loved the pool and having beach chairs & sand toys on hand was an added bonus. Can't wait to book our next vacation in the same home...”
- Review left on 05/04/2016

$199.00

Excellent (2 reviews)

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from $199.00 / night

(7)

1 / 84

Anna Maria Island Condo

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
“Impeccable beach house! All the amenities one would want. Great Weber gas grill, (almost) private pool, brand new kitchen, brand new front loader washer/dryer (free). Cross the street and you're on the public beach, or drive 10 min north or south...”
- Review left on 11/23/2016

$157.00

Excellent (7 reviews)

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from $157.00 / night

1 / 48

Anna Maria Island House

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

$157.00

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from $157.00 / night

1 / 81

Anna Maria Island Condo

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

$165.00

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from $165.00 / night

1 / 8

Anna Maria Island Condo

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

$165.00

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from $165.00 / night

1 / 34

Bradenton Beach House

  • 2
  • 5
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$195.00

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from $195.00 / night

1 / 24

Anna Maria Island House

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

$195.00

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from $195.00 / night

1 / 34

Anna Maria Island House

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

$195.00

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from $195.00 / night

1 / 35

Anna Maria Island House

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

$195.00

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from $195.00 / night

1 / 34

Anna Maria Island House

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

$390.00

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from $390.00 / night