12 Fantastic Anna Maria Island Rentals With Beach Views

Stunning sunsets, succulent seafood and some of the softest, whitest and cleanest sands in the country await you on Anna Maria Island. Located off Florida’s beautiful Gulf Coast, this barrier island is a slice of serendipity on the south side of Tampa Bay. Beloved by our readers and writers, this quaint Florida beach town is home to one of the most beautiful beaches in the United States.

Popular with retirees and snowbirds, this tropical paradise is only 11 kilometers long and actually comprises three towns: Anna Maria, Holmes Beach and Bradenton Beach. Rent a golf cart, bike, or ride the free island cart to the restaurants, bars, and shops. After a day of sunbathing and searching for seashells along the warm, peaceful azure waters, you’ll need a place to stay. Here are some fabulous rentals on Anna Maria Island to consider for your next getaway.

Tropicotage

Minutes from the heart of Anna Maria Village, this four-bedroom vacation rental offers sunrise views of Tampa Bay. The backyard features a heated swimming pool, outdoor dining area and putting green. By the pool you will find a bar, a table tennis table, televisions and a sofa.

A balcony off the upstairs master bedroom offers beautiful views of the bay, while the large sun deck offers stunning beach and pool views.

An additional guest house makes it an ideal place to stay for a family or a group. Rent a golf cart and bikes to get to restaurants, bars and shops.

Bedrooms: 4

Bathrooms : 3

Sleeping: 8

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Bayside Home With Pool

Bayside Home With Pool

Located on the tip of Anna Maria Island, this luxurious three-bedroom vacation home is right across from the beach. Take in views of Tampa Bay and the Sunshine Skyway Bridge. Amenities include a pool and hot tub, outdoor shower, putting green, covered porch, TV, and wet bar. Right outside the door, Bayfront Park offers tons of things to do. Hop on the free trolley a block away to head south to Holmes Beach and Bradenton Beach.

Bedrooms: 3

Bathrooms : 3.5

Sleeping: 8

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Gulf Front House With Pool

Gulf Front House With Pool

Nestled on the shores of the Gulf of Mexico, this Spanish-style beachfront home is the perfect place to stay on the northern end of Anna Maria Island. Spend your days lounging by the pool while taking in views of the sparkling blue waters and white sands. Beach chairs and a beach cart are provided. Be sure to claim the master suite if you wish to take advantage of its sauna!

Bedrooms: 4.5

Bathrooms : 3.5

Sleeping: ten

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Holmes Beach Cottage

Holmes Beach Cottage

Located in Holmes Beach, this gulf front cottage is one of four beautifully appointed suites that are just steps from the beach. Watch the dolphins swim along the shore as you sip your morning coffee on the communal deck, which also offers stunning sunset views. Outdoor showers make it easy to rinse off the beach.

Nearby Manatee Public Beach offers a playground and a volleyball court. Shops, restaurants and a grocery store are all within walking distance. Each accommodation comes with a parking space.

Bedrooms: 1

Bathrooms : 1

Sleeping: 4

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Holmes Beach Bungalow

Holmes Beach Bungalow

Step through the door to this tropical paradise by the gulf and you’ll find yourself on white sand with a view of azure blue water. One of four units, this vacation rental features a private patio perfect for dolphin watching and beautiful sunsets.

Bedrooms: 1

Bathrooms : 1

Sleeping: 4

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Holmes Beach House

Holmes Beach House

Nestled along the sugary white sands of scenic Anna Maria Island’s beautiful Holmes Beach, this four-bedroom vacation rental features a golf cart, bicycles, beach cart, beach toys, pool and a hot tub. The master suite offers beach and gulf views while the large balcony faces west, virtually guaranteeing a glorious sunset. A mini-fridge, stove and microwave in the upstairs laundry room makes it possible to share the house with another family. Kids will love the retro arcade game! Everyone will love the sugary white sand, which is just a minute from the back door.

Bedrooms: 4

Bathrooms : 4

Sleeping: 8

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Cottage By The Sea

Cottage By The Sea

Located in the heart of Holmes Beach, this three-bedroom beachfront rental offers front-row seating to watch Anna Maria Island’s famous sunsets from its private patio. It also has a great central location which is close to everything. Many shops and restaurants are within walking distance in five minutes. Take the trolley to Pine Avenue at the north end or Bridge Street at the southern end of the island.

Bedrooms: 3

Bathrooms : 3

Sleeping: 6

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Holmes Beach Condo

Holmes Beach Condo

Steps from pristine white sand beaches, this three bedroom oceanfront condo is located in Holmes Beach. Watch the sun set over the Gulf from your balcony. Relax by the large heated swimming pool with whirlpool. Other common areas include a gazebo and a picnic and grilling area. Parking for two vehicles is included.

Bedrooms: 3

Bathrooms : 2.5

Sleeping: 6

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Holmes Beach House With Pool

Holmes Beach House With Pool

This luxury beachfront abode offers views of the waves and a heated pool. Grill a dinner on the balcony or relax by the fire on the back patio watching the sun go down over the gulf. Two parking spaces are included. A minimum stay of seven nights is required, but who wants to spend less than a week here?

Its central location just south of downtown Holmes Beach is close to everything while offering tranquility. The trolley stops nearby so you can easily head south to lovely Coquina Beach or north to Pine Avenue for restaurants and bars, shopping and the Anna Maria Pier City.

Bedrooms: 4

Bathrooms : 4.5

Sleeping: 8

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Bradenton Beach House

Bradenton Beach House

Located on the Gulf of Bradenton Beach, this three bedroom unit is in a sea glass colored building that houses three other units. Take in panoramic beach views from the living room or step out onto the balcony to watch the sun set over the water. Our favorite part (besides being on the beach, of course) is the mermaid tile in the bathroom shower!

Bedrooms: 3

Bathrooms : 2

Sleeping: 6

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Bradenton Beach Cottage

Bradenton Beach Cottage

Don’t worry, this vacation rental isn’t just a hammock, but this charming little seaside cottage has one! It also offers many other places to admire the picturesque white sand beach. Swing on the porch, sip coffee in a captain’s chair, sunbathe in a lounge chair, and enjoy the sunset from the Adirondack chairs.

Bedrooms: 1

Bathrooms : 1

Sleeping: 2

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Bradenton Beach Condo

Bradenton Beach Condo

There isn’t much more beachfront than this ground floor condo on the Gulf of Mexico. Your feet touch the sand as soon as you step out of your covered veranda. Beach chairs and beach toys are provided, as well as a parking space. Note that unlike the rest of the rentals on this list, it doesn’t have a grill, but restaurants and shops are within walking distance.

Bedrooms: 2

Bathrooms : 1

Sleeping: 4

Book now

Related reading:

  1. 19 Florida Gulf Coast Monthly Rentals Perfect for Snowbirds
  2. 9 Fantastic St. Petersburg, Florida Experiences and Where to Eat and Stay
  3. Fantastic Experiences in Tampa, Florida for Mature Travelers

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