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Anna Maria Island Vacation Rentals & Beach Rentals - 58 Rentals Available

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58 Vacation rentals

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

(5)

1 / 27

Holmes Beach Condo

  • 2
  • 4
  • Min stay varies
  • Child friendly
  • Air conditioning
“My Husband ,Son & I had a wonderful time at the Condo,it was clean ,comfortable & near the beach ,shops & the bus stops.I could not ask for anything better ,will be looking to rent again in the future”
- Review left on 09/01/2015

$100

Excellent (5 reviews)

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from $100 / night

(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

$225

Very Good (18 reviews)

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from $225 / 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

1 / 19

Holmes Beach House

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

from $199 / night

(6)

1 / 29

Anna Maria Island House

  • 4
  • 8
  • 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

$390

Excellent (6 reviews)

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from $390 / 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

(18)

1 / 24

Anna Maria Island Cottage

  • 2
  • 5
  • 7 nights min
  • Child friendly
  • Air conditioning
“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

$93

Excellent (18 reviews)

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from $93 / 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

1 / 38

Bradenton Beach House

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

from $500 / night

1 / 34

Holmes Beach House

  • 5
  • 11
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $429 / night

(20)

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 (20 reviews)

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from $150 / night

(1)

1 / 47

Holmes Beach House

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“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

Excellent (1 reviews)

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from $555 / night

(2)

1 / 20

Holmes Beach Townhouse

  • 3
  • 6
  • 7 nights min
  • 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

$236

Excellent (2 reviews)

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from $236 / night

(4)

1 / 30

Anna Maria Island House

  • 3
  • 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“This home is exactly as pictured and the owners are so great to work with! We loved all the accommodations of the home and it was very, very clean and well maintained! It had everything we needed to enjoy both the pool and the beach. With 3...”
- Review left on 11/07/2016

$214

Excellent (4 reviews)

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from $214 / night

1 / 20

Bradenton Beach Condo

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

$343

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from $343 / 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

(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 / 32

Anna Maria Island House

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

from $291 / 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

(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

(6)

1 / 41

Bradenton Beach Condo

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • 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

1 / 19

Holmes Beach Townhouse

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

from $199 / 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

$250

Excellent (7 reviews)

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from $250 / night

1 / 24

Bradenton Beach House

  • 6
  • 13
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $500 / 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

(9)

1 / 22

Bradenton Beach Cottage

  • 1
  • 4
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning
“Good location. Clean, well supplied, good daily maid service. Not much area for being pet friendly for bathroom and for walking dog. Parking lot flooded with minimal rain. No overhang on porch at door or over chairs to get out of rain to even enjoy...”
- Review left on 08/08/2016

$155

Very Good (9 reviews)

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from $155 / night

1 / 24

Holmes Beach House

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

from $400 / 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

$350

Excellent (5 reviews)

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from $350 / night

(6)

1 / 19

Holmes Beach Townhouse

  • 3
  • 8
  • 2 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
“This home is beautifully decorated and well maintained. The backyard is meticulously landscaped and provides for a private relaxing environment with a short 2 block walk to your private beach access. The owners provide lots of information on...”
- Review left on 06/29/2015

$157

Very Good (6 reviews)

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from $157 / 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

1 / 81

Anna Maria Island Condo

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

$200

Book

from $200 / night

(2)

1 / 25

Holmes Beach Townhouse

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

$285

Excellent (2 reviews)

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from $285 / night

1 / 4

Bradenton Beach Cottage

  • 1
  • 3
  • 1 night min
  • Air conditioning

$175

Book

from $175 / night

1 / 24

Holmes Beach House

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

from $350 / night

(7)

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 (7 reviews)

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from $250 / 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

(2)

1 / 18

Holmes Beach House

  • 3
  • 7
  • Min stay varies
  • Swimming pool
  • Ask about children
  • 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

$250

Excellent (2 reviews)

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from $250 / night

1 / 47

Bradenton Beach House

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

from $758 / 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

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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