12 Fantastic Anna Maria Island Rentals With Beach Views

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12 Fantastic Anna Maria Island Rentals With Beach Views

aerial view of beach and pool from Anna Maria vacation rental
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    All products featured on TravelAwaits are independently selected by our writers and editors. We may earn commission when you click on or make a purchase via our links.

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

    Popular with retirees and snowbirds alike, this tropical paradise is just 7 miles long and is actually comprised of three cities: Anna Maria, Holmes Beach, and Bradenton Beach. Rent a golf cart, bicycle, or take the free island trolley to restaurants, bars, and boutiques. After a day of sunning and searching for shells along the warm, peaceful azure waters, you’ll need a place to stay. Here are some fabulous Anna Maria Island rentals to consider for your next getaway.

    Tropicottage

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    Minutes from the heart of Anna Maria Village, this four-bedroom vacation rental offers sunrise views over Tampa Bay. The courtyard features a heated pool, outdoor dining, and a putting green. By the pool, you’ll find a bar, ping pong table, TVs, and a couch.

    A balcony off the primary bedroom upstairs boasts beautiful bay views, while the large sun deck offers sweeping views of the beach and pool area.

    An additional guest cottage makes this a great place to stay for a family or group. Rent a golf cart and bikes to ride to restaurants, bars, and boutiques.

    Bedrooms: 4
    Bathrooms: 3
    Sleeps: 8

    Bayside House With Pool

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    Situated on the tip of Anna Maria Island, this luxurious three-bedroom vacation home lies directly across from the beach. Enjoy 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. Just outside the door, Bayfront Park offers tons of things to do. Hop on the free trolley a block away to head south to nearby Holmes Beach and Bradenton Beach.

    Bedrooms: 3
    Bathrooms: 3.5
    Sleeps: 8

    Gulf-Front House With Pool

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

    Bedrooms: 4.5
    Bathrooms: 3.5
    Sleeps: 10

    Holmes Beach Cottage

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    Located in Holmes Beach, this Gulf-front cottage is one of four beautifully appointed suites that lie a few steps from the beach. Watch dolphins swim along the shoreline as you sip your morning coffee on the shared patio, which also offers amazing sunset views. Outdoor showers make rinsing the beach away a breeze.

    Nearby Manatee Public Beach offers a playground and volleyball court. Stores, restaurants, and a grocery are all a short walk away. Each unit comes with one parking space.

    Bedrooms: 1
    Bathrooms: 1
    Sleeps: 4

    Holmes Beach Bungalow

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    Walk out the door of this tropical Gulf-front paradise, and you’ll find yourself on white sand looking out over azure blue water. One of four units, this vacation rental has a private patio that’s perfect for dolphin watching and staring at the stunning sunsets.

    Bedrooms: 1
    Bathrooms: 1
    Sleeps: 4

    Holmes Beach House

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    Nestled along the sugary white sands of quaint Anna Maria Island’s beautiful Holmes Beach, this four-bedroom vacation rental includes a golf cart, bicycles, a beach cart, beach toys, a pool, and a hot tub. The primary suite offers views of the beach and Gulf while the large balcony faces west, practically guaranteeing a beautiful sunset. A mini-fridge, stove, and microwave in the laundry room upstairs make it convenient to share the home with another family. Kids will love the retro arcade game! Everyone will love the sugary white sands, which sit just one minute from the back gate.

    Bedrooms: 4
    Bathrooms: 4
    Sleeps: 8

    Cottage By The Sea

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    Located in the heart of Holmes Beach, this three-bedroom beachfront rental offers front-row seats to Anna Maria Island’s famous sunsets from its private patio. It also has a great central location that’s close to everything. Many shops and restaurants can be reached on foot within five minutes. Take the trolley to Pine Avenue on the north end or Bridge Street on the south end of the island.

    Bedrooms: 3
    Bathrooms: 3
    Sleeps: 6

    Holmes Beach Condo

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    Steps away from pristine white sand beaches, this three-bedroom beachfront condo can be found in Holmes Beach. Watch the sun go down over the Gulf from your balcony. Lounge by the large heated pool, complete with hot tub. Other common areas include a gazebo area and picnic and grill area. Parking for two vehicles is included.

    Bedrooms: 3
    Bathrooms: 2.5
    Sleeps: 6

    Holmes Beach House With Pool

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    This luxury beachside abode features views of the surf and a heated pool. Grill up some dinner on the balcony or relax by the fire on the back patio as you watch the sun go down over the Gulf. Two parking spaces are included. A seven-night minimum stay is required, but who would want to spend less than a week here?

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

    Bedrooms: 4
    Bathrooms: 4.5
    Sleeps: 8

    Bradenton Beach House

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    Located on the Gulf in 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 go down 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
    Sleeps: 6

    Bradenton Beach Cottage

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    Don’t worry, this vacation rental isn’t just a hammock, but this lovely little beachfront cottage does come with one! It also offers plenty of other places to take in views of the picturesque white sand beach. Swing on the porch, sip coffee from a captain’s chair, sun in a lounge chair, and enjoy the sunset from the Adirondack chairs.

    Bedrooms: 1
    Bathrooms: 1
    Sleeps: 2

    Bradenton Beach Condo

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    It doesn’t get much more beachfront than this ground-level condo on the Gulf of Mexico. Your feet hit the sand as soon as you step off your covered lanai. Beach chairs and beach toys are provided, as is one parking spot. Do note that unlike the rest of the rentals on this list, it does not have a grill, but restaurants and shops can be found within walking distance.

    Bedrooms: 2
    Bathrooms: 1
    Sleeps: 4

    Related Reading:

    1. 19 Monthly Rentals On Florida’s Gulf Coast Perfect For Snowbirds
    2. 9 Fantastic Experiences In St. Petersburg, Florida, Plus Where To Eat And Stay
    3. Fantastic Experiences In Tampa, Florida For Mature Travelers