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Anna Maria Island Vacation Rentals & Beach Rentals - 79 Rentals Available

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79 Vacation rentals

(5)

1 / 26

Bradenton Beach Apartment

  • 1
  • 5
  • 2 nights min
  • Air conditioning

Responds fast! Avg. 3 hours 2 minutes

$338.00

Excellent (5 reviews)

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from $338.00 / night

(3)

1 / 31

Bradenton Beach Cottage

  • 2
  • 5
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly

Responds fast! Avg. 3 hours 2 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

$189.00

Very Good (3 reviews)

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from $189.00 / night

(28)

1 / 21

Anna Maria Island Cottage

  • 2
  • 5
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden

Responds fast! Avg. 1 hour 22 minutes

“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

$218.00

Excellent (28 reviews)

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from $218.00 / night

1 / 19

Bradenton Beach Cottage

  • 1
  • 3
  • 2 nights min
  • Car not necessary
  • Air conditioning

Responds fast! Avg. 3 hours 2 minutes

$229.00

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from $229.00 / night

(1)

1 / 33

Anna Maria Island Villa

  • 2
  • 5
  • 2 nights min
  • Child friendly

Responds fast! Avg. 3 hours 2 minutes

$304.00

Excellent (1 reviews)

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from $304.00 / night

(23)

Certificate of Excellence

1 / 44

Anna Maria Island House

  • 4
  • 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 1 minutes

Travelers’ Choice award

“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

$487.00

Excellent (23 reviews)

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from $487.00 / night

(7)

1 / 16

Holmes Beach Villa

  • 3
  • 6
  • 7 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

$229.00

Very Good (7 reviews)

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from $229.00 / night

(2)

1 / 72

Anna Maria House

  • 2
  • 6
  • 2 nights min
  • Swimming pool
  • Air conditioning
  • Private garden

Responds fast! Avg. 3 hours 2 minutes

$418.00

Excellent (2 reviews)

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from $418.00 / night

(2)

1 / 31

Anna Maria Island Cottage

  • 1
  • 3
  • 2 nights min
  • Beach/lakeside relaxation
  • Car not necessary

Responds fast! Avg. 3 hours 2 minutes

$327.00

Very Good (2 reviews)

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from $327.00 / night

(3)

1 / 36

Bradenton Beach Cottage

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

Responds fast! Avg. 3 hours 2 minutes

$189.00

Excellent (3 reviews)

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from $189.00 / night

(21)

1 / 17

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

$201.00

Very Good (21 reviews)

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from $201.00 / night

(5)

1 / 24

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

$126.00

Excellent (5 reviews)

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from $126.00 / night

1 / 26

Bradenton Beach Villa

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

$262.00

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from $262.00 / night

Your search has been expanded 19.7 miles to include more rentals

1 / 33

Bradenton House - 8.4 miles away

  • 3
  • 6
  • 2 nights min
  • Child friendly
  • Air conditioning

Responds fast! Avg. 54 minutes

$138.00

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from $138.00 / night

(1)

1 / 26

Sarasota Cottage - 16.8 miles away

  • 1
  • 3
  • 7 nights min
  • Air conditioning
  • Private garden

$116.00

Excellent (1 reviews)

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from $116.00 / night

1 / 15

Bradenton House - 9.7 miles away

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 54 minutes

$457.00

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from $457.00 / night

(1)

1 / 16

Bradenton Condo - 6.3 miles away

  • 3
  • 6
  • 120 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
“We vacationed at this villa during February and March 2011. It is spacious and quite nicely furnished. We especially enjoyed the setting - the view from every window is of trees and shrubs with no other dwellings visible. One minor drawback of its...”
- Review left on 04/28/2011

$107.00

Very Good (1 reviews)

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from $107.00 / night

1 / 9

Lakewood Ranch Cottage - 19.3 miles away

  • 1
  • 2
  • 5 nights min
  • Nearest beach 10 mi
  • Air conditioning
  • Private garden

Responds fast! Avg. 3 hours 10 minutes

$126.00

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from $126.00 / night

(7)

1 / 15

Bradenton Apartment - 19.3 miles away

  • 1
  • 2
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Air conditioning

Responds fast! Avg. 3 hours 10 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

1 / 8

Sarasota Condo - 12.7 miles away

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

Responds fast! Avg. 2 hours 14 minutes

$57.00

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from $57.00 / night

1 / 36

St. Petersburg House - 17.9 miles away

  • 4
  • 10
  • 3 nights min
  • Child friendly
  • Air conditioning

$1,374.00

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from $1,374.00 / night

1 / 24

St. Petersburg Manor house - 18.9 miles away

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,145.00

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from $1,145.00 / night

(3)

1 / 11

Sarasota Condo - 16.8 miles away

  • 2
  • 6
  • 30 nights min
  • Nearest beach 20 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 2 hours 48 minutes

“This condo was extremely well appointed and had everything that we needed. We stayed 3 months and enjoyed every minute. The owners were gracious and responsive to every question. The view was outstanding. How much did we like it -we are renting it...”
- Review left on 03/30/2015

$115.00

Excellent (3 reviews)

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from $115.00 / night

(11)

1 / 20

Bradenton House - 6.6 miles away

  • 3
  • 6
  • min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
“The location of this property is a perfect area. Just as described by the owner. House is fully equipped including a hand mixer. We enjoyed watching the water sports on the bay from the patio. Lots of parks and popular beaches within 5 mile radius...”
- Review left on 04/07/2017

$189.00

Very Good (11 reviews)

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from $189.00 / night

(1)

1 / 13

Lakewood Ranch House - 19 miles away

  • 2
  • 4
  • min stay varies
  • Nearest beach 15 mi
  • Swimming pool
  • Air conditioning

$229.00

Average (1 reviews)

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from $229.00 / night

(3)

1 / 43

Redington Beach Manor house - 19.7 miles away

  • 5
  • 13
  • 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

1 / 25

Madeira Beach Condo - 19.6 miles away

  • 1
  • 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

$95.00

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from $95.00 / night

(12)

1 / 23

Bradenton House - 16.9 miles away

  • 3
  • 6
  • min stay varies
  • Nearest beach 15 mi
  • 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

$229.00

Excellent (12 reviews)

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from $229.00 / night

1 / 16

Bradenton House - 10.2 miles away

  • 3
  • 4
  • min stay varies
  • Nearest beach 10 mi
  • Swimming pool
  • Air conditioning

$189.00

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from $189.00 / night

(2)

1 / 3

St. Petersburg Condo - 18.8 miles away

  • 1
  • 2
  • 30 nights min
  • Ask about children
  • Air conditioning
“I stayed for the month of May while finding a place for our move. Place is in great location with plenty to walk to. 10 minute walk and you are at great restaurants, movie theatre, and the bay. Place is great for a single person or a couple, and...”
- Review left on 06/01/2016

$39.00

Excellent (2 reviews)

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from $39.00 / night

(20)

1 / 120

St. Petersburg Condo - 12.5 miles away

  • 2
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool

Responds fast! Avg. 2 hours 14 minutes

“We had stayed all around Florida , but Never had a view like this, water everywhere, from all the windows. When you see the pictures they are gorgeous but in real life Wow. I think this is one of the best condo's we have stayed in. The owners are...”
- Review left on 05/30/2017

$228.00

Excellent (20 reviews)

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from $228.00 / night

1 / 21

Madeira Beach Condo - 19.2 miles away

  • 3
  • 8
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

$258.00

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from $258.00 / night

(3)

1 / 34

Bradenton Condo - 17.1 miles away

  • 2
  • 6
  • 3 nights min
  • Nearest beach 12 mi
  • Swimming pool
  • Child friendly

$144.00

Excellent (3 reviews)

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from $144.00 / night

1 / 19

Palma Sola House - 6.7 miles away

  • 6
  • 18
  • 7 nights min
  • Child friendly

$300.00

Inquire

from $300.00 / night

(4)

1 / 14

Madeira Beach Condo - 19.4 miles away

  • 2
  • 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Enjoyed the vacation. Rented 2 condos for family of10 for the week of July 4. Nice rooms, great beach, and amazing 4th of July fireworks on the beach from 8:30 until nearly 11:00. never seen fireworks like that before...”
- Review left on 07/18/2015

$172.00

Very Good (4 reviews)

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from $172.00 / night

1 / 20

Madeira Beach Condo - 18.1 miles away

  • 1
  • 3
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$149.00

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from $149.00 / night

(8)

1 / 17

St. Petersburg Condo - 13.1 miles away

  • 2
  • 4
  • 2 nights min
  • Swimming pool
  • Air conditioning
  • Pet friendly
“We thoroughly enjoyed our stay in this beautiful condo overlooking Boca Ciega Bay.. Very clean, comfortable home, what a nice view of the bay with dolphins regularly swimming by! The owner, Ken, was stellar to deal with, all our needs were totally...”
- Review left on 05/21/2016

$86.00

Excellent (8 reviews)

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from $86.00 / night

1 / 26

Bradenton House - 6.7 miles away

  • 4
  • 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$165.00

Inquire

from $165.00 / night

(29)

1 / 26

Treasure Island Cottage - 15 miles away

  • 1
  • 4
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
“This was such a fun cottage to stay in for the week. It was very clean, had everything that we needed, and it was close to so many fun places in Treasure Island and Madeira Beach with John's Pass. Michael and Gitta made sure that we had everything...”
- Review left on 07/13/2016

$92.00

Very Good (29 reviews)

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from $92.00 / night

1 / 18

Bradenton Apartment - 9.2 miles away

  • 2
  • 5
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$149.00

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from $149.00 / 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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