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Anna Maria Island Beach Vacation Rentals, Beach Rentals & More - 22 Rentals Available.

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22 Vacation rentals

Filters applied: Beach

(18)

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

$200

Very Good (18 reviews)

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from $200 / night

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(1)

1 / 20

Bradenton Beach Cottage

  • 2
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly

$150

Very Good (1 reviews)

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from $150 / night

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1 / 21

Anna Maria House

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

$500

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from $500 / night

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(2)

1 / 20

Bradenton Beach Cottage

  • 2
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$135

Excellent (2 reviews)

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from $135 / night

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1 / 20

Bradenton Beach Condo

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$414

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from $414 / night

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1 / 28

Bradenton Beach Condo

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$114

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from $114 / night

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(28)

1 / 97

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

$250

Very Good (28 reviews)

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from $250 / night

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(29)

1 / 22

Bradenton Beach Apartment

  • 2
  • 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“Wonderful experience. Place was as advertised and more. Right across from the beach and close to everything. Lynn was a pleasure to work with. I have already started working on my stay in April with her. Highly recommend it as long as you don't get...”
- Review left on 11/05/2016

$100

Very Good (29 reviews)

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from $100 / night

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(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

$200

Very Good (5 reviews)

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from $200 / night

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(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

$350

Excellent (5 reviews)

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from $350 / night

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1 / 81

Anna Maria Island Condo

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

$200

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from $200 / night

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(2)

1 / 22

Anna Maria House

  • 8
  • 16
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“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

$599

Excellent (2 reviews)

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1 / 24

Holmes Beach House

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

$350

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(68)

1 / 67

Bradenton Beach Cottage

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“We were suppose to go to West Palm Beach and the hurricane at that time changed our plans and we decided to look around at a place I had been to before--Anna Maria Island. We found this ad on the Sugar Shack and we were lucky it was not rented the...”
- Review left on 02/22/2017

$214

Excellent (68 reviews)

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from $214 / night

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(1)

1 / 44

Anna Maria Island Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“This was our first time renting, we usually stay at a hotel. The unit was exactly like the photos and clean as well. I had some trouble with the garbage disposal so I called the property management and they were very professional and offer to put...”
- Review left on 07/05/2016

$150

Excellent (1 reviews)

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from $150 / night

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(2)

1 / 5

Holmes Beach Condo

  • 2
  • 4
  • 14 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“It was in a great location although we had a room on the second floor and crows nest was kind of in front of us and blocked the beautiful view. If I rented there again I would want a different room. The room was nice and how nice to have a lanai...”
- Review left on 10/22/2015

$159

Very Good (2 reviews)

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from $159 / night

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1 / 21

Anna Maria House

  • 5
  • 12
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly

$700

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from $700 / night

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1 / 14

Anna Maria House

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

$500

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from $500 / night

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(5)

1 / 16

Holmes Beach Villa

  • 3
  • 16
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“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

$329

Excellent (5 reviews)

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(1)

1 / 78

Anna Maria Island Condo

  • 1
  • 3
  • 6 nights min
  • 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

Excellent (1 reviews)

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from $120 / night

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1 / 21

Anna Maria House

  • 5
  • 11
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly

$600

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from $600 / night

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(8)

1 / 72

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

$250

Excellent (8 reviews)

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from $250 / night

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Your search has been expanded 13.1 miles to include more rentals

(2)

1 / 11

Bradenton Apartment - 2.3 miles away

  • 2
  • 4
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool

$74

Excellent (2 reviews)

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from $74 / night

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(2)

1 / 4

Cortez Cottage - 2.8 miles away

  • 2
  • 4
  • 30 nights min
  • Beach/lakeside relaxation
  • Air conditioning
  • Pet friendly
“This apartment had a beautiful open concept, nicely decorated. The place was supplied with nice quality furniture and cooking apparatus. Quiet and right on the canal, close to everything. Owners were above and beyond for help, and just a click...”
- Review left on 01/02/2015

$92

Very Good (2 reviews)

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1 / 9

Cortez Townhouse - 2.8 miles away

  • 4
  • 6
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$295

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(1)

1 / 49

Longboat Key House - 5 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Our Stay at the Conrad Cabana on Longboat Key was more than we had wished for. The moment we entered the home we knew that we would be very comfortable and we were. Throughout the rental process everything went smoothly and when we arrived we were...”
- Review left on 02/21/2016

$400

Excellent (1 reviews)

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from $400 / night

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(5)

1 / 44

Longboat Key House - 6 miles away

  • 5
  • 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“The house is stunning, but that is nothing compared to the location! Right on the beach, beautiful views! Kids loved the pool while the adults loved the relaxation. I can't think of anything negative to say...we truly enjoyed our time at the house...”
- Review left on 02/09/2017

$800

Excellent (5 reviews)

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(4)

1 / 16

Bradenton House - 6.4 miles away

  • 3
  • 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Was so hard finding a house that met the needs of our family of 10. But, Cappobianco's family just went above and beyond with this beautiful and super completed house, I called Paradise! Can't thank them enough for allowing us to spend our family...”
- Review left on 06/16/2016

$243

Excellent (4 reviews)

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1 / 28

Longboat Key Condo - 6.7 miles away

  • 1
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$155

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(1)

1 / 26

Longboat Key Townhouse - 7 miles away

  • 2
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$99

Excellent (1 reviews)

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(21)

1 / 32

Palmetto House - 7.5 miles away

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Two days after we arrived, we booked for 2018! Capt Julie and Pamela have made an enchanted, whimsical oasis where you can find a mermaid sitting on a bench in the garden, a charming metal tortoise lounging by the pool and an open, flowing old...”
- Review left on 02/20/2017

$300

Excellent (21 reviews)

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(1)

1 / 22

Longboat Key Condo - 7.8 miles away

  • 3
  • 6
  • 7 nights min
  • 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

$214

Very Good (1 reviews)

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(15)

1 / 48

Longboat Key Condo - 7.8 miles away

  • 2
  • 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“The two balconies and lanai overlooking the fabulous Gulf of Mexico provid a beautiful and ever-changing view of Nature's best work. Condo is large, clean and comfortably furnished with wifi and 3 TV's. Every convenience has been thought of, from...”
- Review left on 04/07/2015

$79

Excellent (15 reviews)

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(1)

1 / 24

Longboat Key Apartment - 8.2 miles away

  • 2
  • 5
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“This was our first time to Longboat Key,Florida. This condo was adorable and in a great location! We arrived at night and once we unlocked the door were so relieved. It is a quaint 2 bedroom 1 bath condo that was so clean and lovely furnishings. We...”
- Review left on 04/11/2016

$135

Very Good (1 reviews)

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1 / 23

Longboat Key Condo - 9.6 miles away

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$94

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(2)

1 / 16

Sarasota Condo - 10.7 miles away

  • 2
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Child friendly
“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

$79

Very Good (2 reviews)

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from $79 / night

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(8)

1 / 24

Longboat Key Condo - 11 miles away

  • 1
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“Enjoyed a 7 night stay in this well furnished 1 bedroom condominium. The owner provided everything to make our stay very comfortable in a very well kept unit. The pool area and grounds are all well maintained We were in walking distance to the...”
- Review left on 12/29/2016

$120

Excellent (8 reviews)

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1 / 16

Longboat Key Condo - 12.8 miles away

  • 3
  • 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$257

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(25)

1 / 24

Bradenton House - 12.9 miles away

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“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

$120

Excellent (25 reviews)

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from $120 / night

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1 / 22

St. Petersburg House - 13.1 miles away

  • 3
  • 10
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$428

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from $428 / night

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