Last Updated March 2, 2021 3/2/2021

13 Coolest Airbnbs in Anna Maria Island, Florida

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There are lots of well-known vacation destinations in the Sunshine State, and then there’s Anna Maria Island. This is one of Florida’s best-kept secrets and a barrier island on the Gulf Coast that’s definitely worth checking out. When you plan your trip to this charming area, you can check out shops and galleries, enjoy local eateries and bars, and spend time on the lovely beaches. Then at the end of the day, stay at one of these fun Airbnb rentals to really settle into the island life and totally relax!

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Dog-Friendly Oasis with Heated Pool Dog-Friendly Oasis with Heated Pool
Credit: airbnb.com
Dog-Friendly Oasis with Heated Pool

Dog-Friendly Oasis with Heated Pool

Vacationers with dogs love this house that is ideal for up to eight human guests. It has a pool, stocked kitchen, tropical landscaping, and is on the quiet northern end of the island. You can walk or bike from here to historic Pine Avenue. From this rental property, it’s a two-minute walk to the Seagrape Beach access and a six-minute walk to Cypress Avenue Beach access. Other amenities here are a 42-inch flat-screen TV, sleeper sofa, and built-in closet system.

Luxury Beach Home Pool at Brand New Luxury Beach Home
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Pool at Brand New Luxury Beach Home

Luxury Beach Home

Anchor Watch is a gorgeous luxury beach home on the north end of Anna Maria Island. It’s a short walk to Bean Point and the Gulf shores. The home’s layout features a pool area on the first level, two bedrooms on the second level, and two bedrooms on the third level. Pets are not allowed here. Other fun things about this property are the private rooftop deck to watch the sunset and feeling like you are in your very own private resort.

Old Florida-Style Cottage with Private Pool Pool at Old Florida-style cottage w private heated pool
Credit: Airbnb.com
Pool at Old Florida-style cottage w private heated pool

Old Florida-Style Cottage with Private Pool

Dogs are welcome to join you at this Airbnb rental that has a private heated pool and is within walking distance from the beach. Known as the “Mangrove Cottage,” it is one house away from the Gulf of Mexico sand, so start your mornings with a walk on the beach. The home has an open floor plan, free Wi-Fi, laundry machines, and coastal colors for the décor. It is a pet-friendly space that also offers parking spaces for three cars in the car port and easy access to the free trolley. Up to six people can stay in this cottage with its two bedrooms and two baths in Anna Maria.

Elevated Beach Cottage with Heated Private Pool Pool at elevated beach cottage with heated private pool
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Pool at elevated beach cottage with heated private pool

Elevated Beach Cottage with Heated Private Pool

Up to six people can stay in this vacation home that has three bedrooms and two baths in Anna Maria. It’s a newly built home with island décor, modern amenities, and brand-new kitchen appliances. The home has multiple balconies to enjoy the sunrises and sunsets. It also has a private pool to take a dip and cool off. Guests can walk to Pine Avenue in just three minutes from here for restaurants and shops. The beach is also within walking distance in just four minutes. Guests who book this Airbnb enjoy the full kitchen, free Wi-Fi, and the beach just a short walk away. To heat the pool above 80 degrees, there is an additional daily charge. Meanwhile, there’s parking here for two vehicles in the driveway and one in the garage.

Turtle Cottage Turtle Cottage
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Turtle Cottage

Turtle Cottage

One of the hottest Airbnbs in Anna Maria is this cottage that sleeps up to four people. It has one bedroom and one bath, and it’s on the quiet north end of the island. You’ll be just two short blocks from the beach here. The sunrises and sunsets can’t be beat when you stay in this 800-square-foot, open-floor-plan cottage. It has a private patio area with a washer and dryer, a heated pool and spa, and a private outdoor shower. The outdoor dining area is nice and has an electric grill and umbrellas. The sleeping arrangements here are a king-size bed in the bedroom and a sofa bed in the common space. Other amenity perks include Wi-Fi, free parking and a TV.

Bay Breeze Cottage Inside of Bay Breeze Cottages #2
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Inside of Bay Breeze Cottages #2

Bay Breeze Cottage

This cottage is available to rent on Airbnb for up to four guests and has one bedroom and one bath. It’s part of a charming boutique resort and has multiple cottages available. With this booking, you’ll have a great kitchen, queen-size bed, and queen-size pull-out sofa. This rental is on the north end of the island and near the beaches, Anna Maria City Pier, and Rod & Reel Pier. The list of amenities at this highly-rated Airbnb includes access to a pool, Wi-Fi, TV, dedicated workspace, kitchen, and laundry.

Canal-Front Cottage with Pool & Hot Tub Pool area - Canalfront Anna Maria Cottage w Pool & Hot Tub
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Pool area - Canalfront Anna Maria Cottage w Pool & Hot Tub

Canal-Front Cottage with Pool & Hot Tub

You’ll love this vacation rental cottage that’s close to the beach and accommodates six guests with two bedrooms and two en-suite bathrooms. There’s a private pool and hot tub to use here. You’ll enjoy the classic Florida architecture, modern décor, and tropical landscaping at this rental. The space also comes with a backyard for outdoor dining, a fully equipped kitchen, free Wi-Fi, and other convenient amenities.

Blue Heron Cottage Outside Blue Heron Cottage
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Outside Blue Heron Cottage

Blue Heron Cottage

This is an adorable cottage in Anna Maria and one that works well for up to four people. It has one bedroom and 1.5 baths on the quiet north end of the island. It’s two short blocks from the beach and near the Fern Street/Alamanda Road intersection. The space is about 800 square feet in size and has an open floor plan. Your host here provides an electric grill, wagon, beach chairs, and umbrella. Other perks are Wi-Fi, TV, laundry, and free parking. You’ll love the sunsets at Bean Point Beach while staying here!

Steps to the Glorious Gulf Steps to the Glorious Gulf
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Steps to the Glorious Gulf

Steps to the Glorious Gulf

Rent this house on Airbnb for up to six people and you’ll have two bedrooms and two baths all to yourselves. It’s on a quiet street in north Holmes Beach and a three-story house that’s perfect for a beach vacation. Guests enjoy the well-stocked kitchen, TVs, Gulf views, beach chairs and towels, and a large master bedroom. Beach access is just two houses away from here, and you also won’t be far from restaurants, bars, and the supermarket.

Adorable One-Bedroom Condo with Shared Pool Adorable One-Bedroom Condo with Shared Pool
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Adorable One-Bedroom Condo with Shared Pool

Adorable One-Bedroom Condo with Shared Pool

For a great apartment option in Anna Maria, consider this one for up to four people. It has one bedroom and one bath, as well as a shared heated pool, patio area, and outdoor seating with BBQ grills. The laundry room is also shared. The kitchen is fully stocked here, and there’s a pull-out sofa to sleep two people. Guests who book this Airbnb enjoy the private patio area and being in a quaint space on the first floor. Dogs are allowed here with some weight and breed restrictions and for an additional pet fee.

Canal-Front Home with Heated Pool, Dock & Lanai Pool area - Canalfront home w/ heated pool, dock & lanai
Credit: Airbnb.com
Pool area - Canalfront home w/ heated pool, dock & lanai

Canal-Front Home with Heated Pool, Dock & Lanai

Here’s an Anna Maria vacation home that accommodates up to eight guests and that has a beautiful pool and hot tub. Guests stay in the three bedrooms and use the two baths here while also enjoying a private canal-front dock. The home is just two blocks from the beach, and the pool is heated. It’s on the quiet north end of Anna Maria Island and has abundant parking. It welcomes guests with a boat dock, Wi-Fi, and plenty of tropical charm.

Cozy Beach House, 800 Steps to Beach Inside Cozy Beach House 800 Steps to Beach
Credit: Airbnb.com
Inside Cozy Beach House 800 Steps to Beach

Cozy Beach House, 800 Steps to Beach

This house can be all yours when you book it on Airbnb for up to three people. It has one bedroom and one bathroom and is just 800 steps from a beautiful beach. It’s a perfect getaway spot for couples because restaurants and entertainment are close by, as well as the free trolley. The Sandbar Restaurant is 400 steps away. Sunbathing, kayaking, and simply relaxing are common things to do when you stay here. The bedroom has a king-size bed, while the home also offers a dedicated workspace, cable TV, Wi-Fi, kitchen, and free parking. Also, simply enjoy the small-town feel of Anna Maria when you are here.

2-Bedroom Beach Home View of 2b/2b beach home on Anna Maria Island
Credit: Airbnb.com
View of 2b/2b beach home on Anna Maria Island

2-Bedroom Beach Home

Here’s an updated family home that’s within two blocks to either side of the island. It’s near a small park and half a block from restaurants. You’ll love the location of this two-bedroom, two-bathroom house for up to six people and the enhanced cleaning and sanitation protocols practiced by the hosts. This home has two queen-size beds and a couch for sleeping. It also offers a laundry machine, a hot tub, Wi-Fi, a kitchen, a dedicated workspace, and free parking. Stay here to be in a safe and quiet neighborhood that’s two blocks from the beach.

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