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Anna Maria Island Beach Vacation Rentals, Beach Rentals & More - 60 Rentals Available.

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60 Vacation rentals

Filters applied: Beach

(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

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(3)

1 / 33

Bradenton Beach Cottage

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

Responds fast! Avg. 3 hours 48 minutes

“My husband and I spent the weekend in this cottage to celebrate his milestone birthday. We found it to be very comfortable and welcoming. I especially love the sunroom for my morning coffee and yoga. We were pleasantly surprised at how comfortable...”
- Review left on 11/23/2017

$172.00

Very Good (3 reviews)

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from $172.00 / 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

$266.00

Very Good (5 reviews)

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from $266.00 / night

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(1)

1 / 21

Anna Maria House

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

Responds fast! Avg. 1 hour 15 minutes

$573.00

Excellent (1 reviews)

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from $573.00 / night

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(5)

1 / 93

Anna Maria Island House

  • 4
  • 8
  • 7 nights min
  • 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

$487.00

Excellent (5 reviews)

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from $487.00 / night

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1 / 53

Holmes Beach House

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

$699.00

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from $699.00 / night

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1 / 14

Anna Maria House

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

Responds fast! Avg. 1 hour 15 minutes

$573.00

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from $573.00 / night

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1 / 70

Anna Maria Island Condo

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary

$344.00

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from $344.00 / night

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(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

$344.00

Very Good (29 reviews)

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from $344.00 / night

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(1)

1 / 31

Anna Maria Island Cottage

  • 1
  • 3
  • min stay varies
  • Beach/lakeside relaxation

Responds fast! Avg. 3 hours 56 minutes

$224.00

Excellent (1 reviews)

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from $224.00 / night

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1 / 81

Anna Maria Island Condo

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$396.00

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from $396.00 / night

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(7)

1 / 16

Holmes Beach Villa

  • 3
  • 6
  • 3 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

$287.00

Very Good (7 reviews)

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from $287.00 / night

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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

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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

$164.00

Excellent (1 reviews)

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from $164.00 / night

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(2)

1 / 36

Bradenton Beach Cottage

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

Responds fast! Avg. 3 hours 48 minutes

$172.00

Excellent (2 reviews)

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from $172.00 / night

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(9)

1 / 100

Anna Maria Island Condo

  • 2
  • 6
  • 7 nights min
  • 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

$401.00

Excellent (9 reviews)

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from $401.00 / night

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1 / 24

Bradenton Beach Condo

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

$344.00

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from $344.00 / night

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Your search has been expanded 19.7 miles to include more rentals

(4)

1 / 19

Bradenton Villa - 17.6 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

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(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

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(25)

1 / 24

Bradenton House - 14.5 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

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(7)

1 / 28

Treasure Island Condo - 16.6 miles away

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

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(18)

1 / 12

Bradenton House - 17.2 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

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(60)

1 / 28

Treasure Island Condo - 15.4 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

$141.00

Excellent (60 reviews)

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from $141.00 / night

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(15)

1 / 57

Treasure Island Condo - 16.9 miles away

  • 1
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 2 hours 11 minutes

“We really enjoyed our stay at Whispers very much.The pool was great and it's a short walk to the beach. The owner was very nice and the rental was nicely kept and clean. Lots of amenities and kindness. Thanks so much for a great time...”
- Review left on 03/15/2017

$92.00

Very Good (15 reviews)

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from $92.00 / night

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(1)

1 / 42

Treasure Island Condo - 15.6 miles away

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

$851.00

Excellent (1 reviews)

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from $851.00 / night

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1 / 29

Cortez Townhouse - 4.8 miles away

  • 4
  • 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 48 minutes

$338.00

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from $338.00 / night

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(1)

1 / 8

Sarasota Condo - 12.7 miles away

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

$63.00

Very Good (1 reviews)

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from $63.00 / night

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(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

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(3)

1 / 38

Redington Beach Manor house - 19.7 miles away

  • 5
  • 12
  • 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

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(7)

1 / 15

Bradenton Apartment - 19.3 miles away

  • 1
  • 2
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Air conditioning

Responds fast! Avg. 3 hours 14 minutes

“What a fantastic place. We had the pleasure of staying in Bob?s studio. Bob thought of everything to make our stay as close to home as possible. We couldn?t have asked for more. The surroundings are pure Florida. The grounds near the studio were well...”
- Review left on 11/19/2016

$144.00

Very Good (7 reviews)

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from $144.00 / night

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(2)

1 / 11

Cortez Cottage - 4.8 miles away

  • 2
  • 4
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.25 mi
  • Air conditioning
“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

$134.00

Very Good (2 reviews)

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from $134.00 / night

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(36)

1 / 46

St. Petersburg Manor house - 16.1 miles away

  • 7
  • 21
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 9 mi
  • Swimming pool
“We invited our extended family to spend Christmas together this year at The Petro Mansion, hoping that the house looked as good in person as it did online. The house is just as beautiful, if not more so, in person! Alex had the house beautifully...”
- Review left on 01/02/2017

$700.00

Excellent (36 reviews)

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from $700.00 / night

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1 / 21

Madeira Beach Condo - 19.2 miles away

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

$264.00

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from $264.00 / night

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1 / 15

Madeira Beach Condo - 19.5 miles away

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

$287.00

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from $287.00 / night

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(1)

1 / 13

St. Pete Beach Condo - 14.6 miles away

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

$202.00

Very Good (1 reviews)

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from $202.00 / night

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(14)

1 / 80

St. Petersburg Condo - 14.6 miles away

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 11 minutes

“Great place, Clean, Awesome room, and at a great location. This place is perfect for visiting St. Petersburg and the Gulf Beaches. Nearby Fort de Soto Park is one of our favorites and it has miles of fabulous beaches. Downtown St Pete is very close...”
- Review left on 03/24/2017

$147.00

Very Good (14 reviews)

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from $147.00 / night

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1 / 36

St. Petersburg Apartment - 12.7 miles away

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

$82.00

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(1)

1 / 38

St. Petersburg Apartment - 12.4 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

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(1)

1 / 31

St. Petersburg Apartment - 12.6 miles away

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

$72.00

Excellent (1 reviews)

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from $72.00 / night

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(1)

1 / 38

St. Petersburg Apartment - 12.6 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

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