Anna Maria Island Vacation Rentals & Beach Rentals - 24 Rentals Available

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1 / 78

Anna Maria Island Condo
1 BR / 1 BA / Sleeps 3 1 3 Min stay varies
Condo / 1 Bedroom / Sleeps 3
1 bedrooms 1 bathroom Sleeps 3
High Speed Internet • Dishwasher • Microwave
"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 ..."
- Peggy Ugasco, Peru, IL.USA
(1) Excellent (1 review)
1 / 17

Anna Maria Island Home
6 BR / 5.5 BA / Sleeps 18 6 18 Min stay varies
Home / 6 Bedrooms / Sleeps 18
6 bedrooms 5.5 bathrooms Sleeps 18
High Speed Internet • Dishwasher • Microwave
"We had 5 families stay for a week and we LOVED it! ! It's beautiful! ! The sand bar was so much fun, we loved watching the dolphins! The raccoons were a HOOT! ! But they are QUICK.....keep the kitchen door closed! ! We couldn't have asked for a ..."
- Melissa Collier Killebrew, Atlanta, GA
(5) Excellent (5 reviews)
1 / 67

Anna Maria Island Cottage
2 BR / 2 BA / Sleeps 6 2 6 7 night min stay
Cottage / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"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 ..."
- Samantha, Hanover, Pa.
(20) Excellent (20 reviews)
1 / 97

Anna Maria Island Condo
2 BR / 2 BA / Sleeps 6 2 6 Min stay varies
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"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 sand..."
- Dan Lupont, Rockford, IL USA
(30) Excellent (30 reviews)
1 / 29

Anna Maria Island Home
4 BR / 3 BA / Sleeps 8 4 8 Min stay varies
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"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..."
- Kim Barna, Oviedo, FL
(6) Excellent (6 reviews)
1 / 93

Anna Maria Island Home
4 BR / 3 BA / Sleeps 8 4 8 Min stay varies
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"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 problems..."
- Phyllis Oldham, Mooresville IN
(6) Excellent (6 reviews)
1 / 54

Anna Maria Island Condo
2 BR / 2 BA / Sleeps 6 2 6 Min stay varies
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"We loved this condo. We had a great view. Everything was very clean. I loved the keyless entry, everyone in our party could come and go without having to worry about a key. You are so close to the beach and walking distance to everything you need. I ..."
- Debbie Cannon, Asheville NC
(5) Excellent (5 reviews)
1 / 92

Anna Maria Island Condo
2 BR / 2 BA / Sleeps 6 2 6 Min stay varies
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"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 nice..."
- Robin and family, Toronto
(5) Excellent (5 reviews)
1 / 11

Anna Maria Island Townhouse
2 BR / 2.5 BA / Sleeps 6 2 6 Min stay varies
Townhouse / 2 Bedrooms / Sleeps 6
2 bedrooms 2.5 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"The unit was clean decorated nicely , having everything you need like home , close to a great beach"
- Laura Fusco, Ny
(10) Excellent (10 reviews)
1 / 24

Anna Maria Island Cottage
2 BR / 1 BA / Sleeps 5 2 5 7 night min stay
Cottage / 2 Bedrooms / Sleeps 5
2 bedrooms 1 bathroom Sleeps 5
High Speed Internet • Microwave • Air Conditioning
"We had a great time at this beautiful cottage Everything was so clean and most comfortable.Joel the owner was great to work with and very helpful.The house is so central for the beach, restaurants and amenities.We cycled on the bikes that are there everyday...."
- Cathy Purcell, Scotland
(17) Excellent (17 reviews)
1 / 20

Anna Maria Island Condo
2 BR / 2 BA / Sleeps 6 2 6 Min stay varies
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
Dishwasher • DVD Player • TV (Cable/Satellite)
"We had a great time on Anna Maria and really enjoyed the lovely relaxing atmosphere of the Dolphin INn, Heron condo. Lovely leafy deck and welcoming lounge and great bedrooms. After a booking axing flight from U.K. It was lovely to arrive to peace and..."
- Robbie Duncan, Isle of Arran Scotland, UK
(4) Excellent (4 reviews)
1 / 84

Anna Maria Island Condo
2 BR / 2 BA / Sleeps 6 2 6 Min stay varies
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
Dishwasher • Microwave • Air Conditioning
"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..."
- Jake Lat, NJ
(6) Excellent (6 reviews)
1 / 25

Anna Maria Island Condo
2 BR / 2 BA / Sleeps 6 2 6 7 night min stay
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"We had a wonderful week at the tropical sunset condoI 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..."
- Bernadette Napoletano, Z├╝rich Switzerland
(3) Excellent (3 reviews)
1 / 19

Anna Maria Island Townhouse
3 BR / 3 BA / Sleeps 8 3 8 Min stay varies
Townhouse / 3 Bedrooms / Sleeps 8
3 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"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 activities..."
- John Kleinschmidt, Macungie Pennsylvania
(3) Excellent (3 reviews)
1 / 44

Anna Maria Island Condo
2 BR / 1 BA / Sleeps 6 2 6 Min stay varies
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 1 bathroom Sleeps 6
High Speed Internet • Dishwasher • Microwave
"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 in..."
- julie young, Georgia
(1) Excellent (1 review)
1 / 35

Anna Maria Island Condo
2 BR / 2 BA / Sleeps 4 2 4 7 night min stay
Condo / 2 Bedrooms / Sleeps 4
2 bedrooms 2 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
"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..."
- Chak Pang, Columbus, Ohio, USA
(6) Excellent (6 reviews)
1 / 29

Anna Maria Island Home
3 BR / 3 BA / Sleeps 8 3 8 7 night min stay
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"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 children,..."
- Catherine Wood, Jacksonville, FL
(4) Excellent (4 reviews)
1 / 27

Anna Maria Island Home
4 BR / 3 BA / Sleeps 10 4 10 3 night min stay
Home / 4 Bedrooms / Sleeps 10
4 bedrooms 3 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
"We stayed at "The Nantucket" for 4 nights and found the whole experience very satisfactory."
- Mike Grinshpon, Orlando, FL USA
(11) Excellent (11 reviews)
1 / 64

Anna Maria Island Cottage
3 BR / 2 BA / Sleeps 6 3 6 7 night min stay
Cottage / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"In the past 5 years I have vacationed at the Sugar Shack 4 yrs. Last year I tried California instead of Anna Maria Island. I was back on the island this year, you cannot beat the beaches, the people and the great Sugar Shack (home away from home). ..."
- Shari Clark, Overland Park, Kansas
(41) Excellent (41 reviews)
1 / 31

Holmes Beach Townhouse - 0.1 mi away
3 BR / 2 BA / Sleeps 6 3 6 Min stay varies
Townhouse / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"We rent the property to celebrate fathers day ! ! with my husband and my daughters family. The house was very clean, have everything we need, we love the clean and heated pool and Jacuzzi, very close to the beach.We recommend this beautiful townhouse,..."
- Tely Castillo, Orlando, Fl
(1) Excellent (1 review)
1 / 18

Holmes Beach Home - 0.1 mi away
3 BR / 2 BA / Sleeps 7 3 7 Min stay varies
Home / 3 Bedrooms / Sleeps 7
3 bedrooms 2 bathrooms Sleeps 7
High Speed Internet • Dishwasher • Microwave
"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!"
- Stacey Bartley, Bloomington, IN
(2) Excellent (2 reviews)
1 / 24

Holmes Beach Townhouse - 0.1 mi away
5 BR / 3 BA / Sleeps 12 5 12 Min stay varies
Townhouse / 5 Bedrooms / Sleeps 12
5 bedrooms 3 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
"Slept 13 comfortably. Great location and pool was a lifesaver with smaller children. I would highly recommend this property! !"
- Samantha Vickers-briones, Atlanta
(2) Excellent (2 reviews)
1 / 20

Holmes Beach Townhouse - 0.1 mi away
3 BR / 3 BA / Sleeps 8 3 8 7 night min stay
Townhouse / 3 Bedrooms / Sleeps 8
3 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"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..."
- Amanda Taylor, Portsmouth, OH
(2) Excellent (2 reviews)
1 / 17

Holmes Beach Townhouse - 0.1 mi away
2 BR / 2 BA / Sleeps 6 2 6 Min stay varies
Townhouse / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"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 ..."
- Hewitt Johnston, Indian Land, South Carolina
(2) Excellent (2 reviews)
1 / 47

Holmes Beach Home - 0.2 mi away
6 BR / 5.5 BA / Sleeps 12 6 12 Min stay varies
Home / 6 Bedrooms / Sleeps 12
6 bedrooms 5.5 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
"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 provide..."
- Jessica Holt, Tampa, FL
(1) Excellent (1 review)
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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!