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Anna Maria Island Vacation Rentals & Beach Rentals - 53 Rentals Available

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53 Vacation rentals

(1)

1 / 19

Holmes Beach Cottage

  • 3
  • 8
  • Min stay varies
  • 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

$271

Excellent (1 reviews)

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from $271 / night

1 / 25

Anna Maria Island Cottage

  • 1
  • 3
  • 1 night min
  • Beach/lakeside relaxation

$200

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from $200 / night

(3)

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

$159

Excellent (3 reviews)

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from $159 / night

(21)

1 / 11

Holmes Beach Townhouse

  • 2
  • 6
  • Min stay varies
  • 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

Very Good (21 reviews)

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from $150 / night

(19)

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

Very Good (19 reviews)

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from $175 / night

(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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from $599 / night

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

(2)

1 / 25

Holmes Beach Townhouse

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

$225

Excellent (2 reviews)

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from $225 / night

1 / 24

Holmes Beach House

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

from $199 / night

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

1 / 47

Bradenton Beach House

  • 11
  • 32
  • 7 nights min
  • Ask about children
  • Air conditioning

from $229 / night

1 / 21

Bradenton Beach Cottage

  • 1
  • 3
  • 1 night min
  • Air conditioning

$175

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from $175 / night

(2)

1 / 24

Bradenton Beach House

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“My family and friends and I rented this property to celebrate my bachelorette weekend and we picked the most perfect house possible! The layout of the house was ideal for accommodating a large number of guests in addition to providing comfortable...”
- Review left on 09/06/2016

$400

Excellent (2 reviews)

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from $400 / night

(7)

1 / 29

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

$400

Excellent (7 reviews)

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from $400 / night

(1)

1 / 24

Holmes Beach Townhouse

  • 5
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • 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

$300

Excellent (1 reviews)

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from $300 / night

(20)

1 / 24

Anna Maria Island Cottage

  • 2
  • 5
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden
“Songbird is a little slice of heaven with everything we needed to have a comfortable stay. We stayed for one week. Joel, the owner, is very thoughtful, and accommodating, and he makes it known that he is there for you if you need him. Which is so...”
- Review left on 05/20/2017

$87

Excellent (20 reviews)

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from $87 / 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

Excellent (3 reviews)

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from $143 / night

(17)

1 / 77

Anna Maria Island Cottage

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“My family and I spent a week in the cottage and surrounding Anna Maria Island.We had a very relaxing vacation by the sea and enjoyed every ammentity the cottage offered.The comforts were those of our own home. Sheila was a perfect host indeed for any...”
- Review left on 08/18/2016

$186

Excellent (17 reviews)

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from $186 / night

1 / 32

Anna Maria Island House

  • 3
  • 10
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

from $291 / night

1 / 21

Anna Maria Island Villa

  • 2
  • 3
  • 1 night min
  • Child friendly

$175

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from $175 / night

1 / 58

Anna Maria House

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

from $400 / night

(6)

1 / 41

Bradenton Beach Condo

  • 2
  • 5
  • Min stay varies
  • 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

$150

Excellent (6 reviews)

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from $150 / night

(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

(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

(2)

1 / 18

Holmes Beach House

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“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

Excellent (2 reviews)

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from $199 / night

(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

1 / 20

Bradenton Beach Condo

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

$272

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from $272 / night

1 / 24

Holmes Beach House

  • 4
  • 11
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $400 / night

1 / 24

Bradenton Beach House

  • 6
  • 14
  • 4 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

from $500 / night

(2)

1 / 20

Holmes Beach Townhouse

  • 3
  • 6
  • 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

$199

Excellent (2 reviews)

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from $199 / night

1 / 19

Holmes Beach House

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $199 / night

(1)

1 / 24

Holmes Beach House

  • 4
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“We found this home clean and comfortable. All especially enjoyed the large open kitchen, dining, and family room areas. The very well-maintained pool and accessories were really appreciated, given red tide prohibited us from enjoying Holmes Beach...”
- Review left on 10/04/2016

$400

Very Good (1 reviews)

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from $400 / night

(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

(1)

1 / 44

Holmes Beach House

  • 6
  • 13
  • Min stay varies
  • Ask about children
  • Air conditioning
“We are a family of 13 and had a great Christmas holiday in this house. The location is great and the house is lovely. I would highly recommend it to anyone...”
- Review left on 01/02/2017

$500

Excellent (1 reviews)

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from $500 / night

(1)

1 / 20

Holmes Beach House

  • 5
  • 10
  • Min stay varies
  • Child friendly

$400

Excellent (1 reviews)

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from $400 / 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

$250

Very Good (5 reviews)

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from $250 / night

(1)

1 / 19

Holmes Beach Townhouse

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$199

Excellent (1 reviews)

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from $199 / night

(1)

1 / 47

Anna Maria House

  • 2
  • 4
  • 1 night min
  • Swimming pool
  • Air conditioning
  • Private garden

$335

Excellent (1 reviews)

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from $335 / night

(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

(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

Excellent (1 reviews)

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from $120 / night

About Anna Maria Island

Laidback and oozing “old Florida” charm, Anna Maria Island is a slice of paradise located on Florida’s famous Gulf Coast. With picturesque beaches known around the world for their beautiful white sand and waters of the clearest turquoise blue, it’s not hard to relax and unwind while on this island in the Gulf of Mexico.
Only seven miles long, the island is divided into three cities: Holmes Beach, Bradenton Beach, and Anna Maria. This gives vacationers plenty of choices when it comes to choosing what to do and where to stay while visiting. An Anna Maria Island vacation rental right on the beach is the perfect option as home base since chain restaurants are pleasantly absent and the area remains untainted by numerous high rise buildings.

Climate

The average year-round temperature in Anna Maria Island is a comfortable 75 degrees making it an ideal destination to visit during any month. In the winter, the skies are cloudless and temperatures range from 75 degrees during the daytime to 50 degrees overnight. Trade winds influence the spring months with sunny, dry days that reach up to 90 degrees. Hot summer temperatures mixed with gentle breezes and cooling rains give way to glorious weather throughout late fall.

Transit

The best way to tour this intimate seven-mile island is by hopping aboard the Anna Maria Island Trolley. It runs north to south from the Anna Maria City Pier to Coquina Beach stopping every few blocks for riders to hop on and off. The best part about it is that it is completely free to riders and offers the perfect opportunity for a burst of refreshing air conditioning on the way to the next activity. Parking can be scarce throughout the island, so the trolley is both a scenic ride and a necessity.

Attractions

Part of Anna Maria Island’s charm is its well-preserved natural beauty. The Anna Maria Island Butterfly Park is a perfect place to see butterflies and plants local to the area. Similarly, the island’s scenic shoreline is an attraction in itself. For people who love to visit the beach and soak up sun, Anna Maria Island has several gorgeous beaches to enjoy.

·       Bean Point is at the very northern tip of the island and is a local secret offering stunning views of the sunset from its pristine and tranquil beach.
·       Manatee Beach is a large public beach with lifeguards on duty and ample beach space for undisturbed bliss.
·       Cortez Beach has calm waters and light surf and is a family-oriented destination. Although no lifeguards are on duty here, it’s one of the best beaches on Anna Maria Island.

The local museums and art galleries are popular attractions as well and great alternatives to outdoor activities. After a morning spent relaxing in an Anna Maria Island vacation rental, people can spend a fun afternoon at the Anna Maria Island Historical Museum and Park. Visitors to the museum and park can learn about the island’s history, take part in a scavenger hunt, and tour the cottage that fell into the bay. Other indoor attractions include The Studio, where exhibits, workshops and lectures are held, as well as Bradenton’s Village of the Arts where artists live and work.

Shopping & Dining

Anna Maria Island offers a variety of shopping options ranging from eclectic seaside shops to popular outlets. Pine Avenue, “the greenest little main street in America,” is lined with boutiques leading up to the City Pier, and Holmes Beach has blocks of shops filled with adorable keepsakes. Mixed in amongst the folksy storefronts is an array of award-winning dining options as well. Whether you’re looking for a grouper sandwich at a casual beachside joint, or a romantic waterfront experience, Anna Maria Island has many options to choose from. With tables in the sand, the Sandbar is always a good choice for a quintessential island meal.

Events

When planning a trip to Anna Maria Island, make arrangements to stay in a vacation rental during one of the city’s awesome annual events. Anna Maria Island Heritage Day in February features the wares and skills of local artists and crafters, and attendees can take part in activities, enjoy lively music and participate in old-fashioned games for kids. In March, Island CityFest features a kids’ zone, arts, crafts and more. Later in Spring, the Bridge Street Merchants host the Blues, Brews & BBQ event for locals and visitors to enjoy. Outdoor Market Sundays take place November through April, and Winterfest in December wraps up the year’s festivities. On Anna Maria Island, fun events happen year-round, so there will always be something to do.

Free from commercialism and where shoes are optional, Anna Maria Island is a premier beach destination that visitors flock to year-round. Book a vacation rental to live the laidback lifestyle of a true Anna Maria Islander and fully experience the island’s Floridian charm. The beaches are beckoning!
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