16+ Best Airbnbs on Anna Maria Island, Florida (for a unique vacation!)

Best places to stay on Anna Maria Island

Looking for the best Airbnbs on Anna Maria Island, Florida? We are here to help you!

Anna Maria Island is one of the most beautiful places in Florida which is why it’s such an excellent choice for a vacation. It gathers pretty much everything Florida is known for. Beautiful beaches, breath-taking sunsets, kids-friendly activities… it truly has it all!

It’s also a great place to disconnect. You really don’t need to use your car on the island. Most of the attractions are reachable on foot and you can always take the free trolley to get around.

Anna Maria Island is also one of the most authentic places in Florida. The locals manage to keep this “Old Florida” vibe and everyone is so friendly!

Choosing to go on a vacation to Anna Maria Island is the best way to enjoy a relaxing getaway in the Sunshine State.

In this article, you will discover 19 amazing Airbnbs on Anna Maria Island!

Disclosure: This post may contain affiliate links, meaning I get a commission if you decide to make a purchase through my links, at no extra cost for you! As an Airbnb Associate, I may earn when you book through these links.

Best Airbnbs in Anna Maria Island Florida

Quick overview of the best Airbnbs on Anna Maria Island, Florida

If you want to jump straight to the good part and see what are the coolest Airbnbs on Anna Maria Island, look no further! Here is a quick summary! For more photos and information, keep scrolling down.

Best Airbnbs on Anna Maria Island

Now is time to discover the best Airbnbs on Anna Maria Island. In this section, you will discover photos and a full description of each property.

Private Paradise

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If you are looking for a little piece of paradise for your next family vacation, this beautiful vacation home in Anna Maria Island will be perfect for you!

There are 4 bedrooms that can accommodate up to 8 people. You will also find 3 bathrooms which is very convenient. Nobody will need to wait for a shower, there should always be one available!

The best thing about this property is the amenities. There is everything you (and your kids) may need! This includes a swimming pool, hot tub, bicycles… There even is a golf cart!

Basically, everything you need to have fun on Anna Maria Island is here!

Finally, in terms of location, it only takes 8 minutes on foot to get to the beach.

Click here to see the latest prices.

Top-rated Anna Maria

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Looking for an Airbnb with hot tub and pool in Anna Maria Island? This one will be perfect for you!

This beautiful vacation rental is a true paradise!

Firstly, let’s talk about the location because this is as good as it gets! The house is situated in Bean Point. This is the best place to stay in Anna Maria Island as you can easily reach the beaches, restaurants and bars on foot.

The house itself is perfect for families. There are 2 bedrooms and it can sleep up to 6 guests. You should be able to spot it straight away as it’s bright blue outside! Very pretty and lively.

The outdoor area is lovely. You will find a swimming pool as well as a spa. There are some chairs where you can rest and read a book. You will also find a little tiki hut with chairs underneath. It’s a great spot to have a drink and chat away!

Click here to see the latest prices.

AMI Retreat

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Tha AMI Retreat is a large house with 3 bedrooms. It can sleep up to 8 guests which is ideal for families.

The house is very spacious. The walls are blue, giving it this very “beachy vibe”.

The best part is the swimming pool area. Not only is the heated private pool amazing but you will also find a spa with a table in the middle. Just picture it, you and your cocktail in the evening, relaxing in the hot tub. It doesn’t get any better than that, does it? There are also chairs where you can lay down and work on your tan.

The kitchen is fully equipped which means you can easily cook all your family meals here. You will also find a terrace upstairs with a dining table. This is a good spot to eat your meals. One of the best things about Florida is that the weather is (almost) always amazing and enjoying eating your brekkie outside is one of the perks.

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Captain’s Quarters

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If you are looking for a beautiful Airbnb with pool in Anna Maria Island, this one is for you!

You will be staying in Holmes Beach which is very close to the main attractions. The free trolley to Anna Maria Island is nearby so you can easily get there whenever you want.

It’s a great place for families. There are 3 bedrooms. The house can sleep up to 6 guests and has a lot of amenities.

The swimming pool area is the highlight of the property. It’s a very relaxing place with palm trees and a dining area. During the day, you will enjoy going for a swim. In the evening, the barbecue will come in very handy.

Inside, you will find a fully equipped kitchen, washing machine, dryer and more.

Click here to see the latest prices.

Turtle Cottage

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If you are looking for a cottage with pool in Anna Maria Island, this Airbnb will be perfect for you!

There is only one bedroom and it can sleep up to 4 guests. This is ideal for a couple or a small family.

The cottage itself is so cute! It’s bright blue, very beachy and the private pool is fantastic. There even is a spa. The outdoor area is very well looked after. There are palm trees and sand, basically the perfect Florida vacation setting. You will also find a dining table with chairs. It’s a good spot to drink a cup coffee in the morning or have lunch.

The amenities include a fully equipped kitchen, a washing machine and dryer as well as a TV.

In terms of location, you will be staying at the north end of the island. This is a quiet location, close to all the main attractions.

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Luxury Beach Sand Castle

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This 4-bedroom house is an excellent option for large families. It sleeps up to 8 guests and is very spacious.

The house is very bright. There is a lot of natural light which is always a good thing. The living room and kitchen are very spacious. You will enjoy cooking there.

There are large french doors. As you step out, you will discover the pool, spa and an outdoor dining area. The space is covered which means you can enjoy it even during the rainy season.

The rooms were beautifully decorated and are spacious as well. Each room has a different type of bed (king, queen, bunk…) so everybody will be happy! It’s also important to mention that there are 2 bathrooms (which comes in very handy for a group of 8).

In terms of location, the house is situated in the southern part of Anna Maria Island, near Holmes Beach. It’s very easy to get there and is a quiet neighbourhood.

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Island in the Sun

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When it comes to dreamy and luxury Airbnbs in Anna Maria Island, this one sets the standard!

The villa is ideally located near the beach. You can easily reach the restaurants, bars and beach on foot. The house itself has 2 bedrooms and can sleep up to 6 guests. There are 2 bathrooms which is very convenient.

The outdoor area is just stunning! It’s quite lush and very well looked after. The pool features a bit of an unusual shape which makes the property even more unique. You will love taking photos there.

The house itself is beautifully decorated. It’s everything you would expect from an Airbnb in Florida. Pastel blue paint, white counter top, wicker chairs, wooden table and floor… it’s just gorgeous! Just looking at it will make you forget all your worries!

It’s also important to note that the house is fully equipped. You can easily cook all your meals here and wash / dry all your clothes.

Click here to see the latest prices.

Island Oasis 5 Lakeview

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If you are looking for a luxury Airbnb on Anna Maria Island, this one will be ideal.

It’s one of the rare properties on the waterfront. You might not be on the beach but staying by the lake is just as wonderful. It’s a very quiet neighbourhood and the house is located in a cul-de-sac. Perfect for families!

There are 2 bedrooms that can accommodate up to 6 guests. You will also find 3 bathrooms which means you will never have to wait for a shower. There should always be one available!

The kitchen is very spacious and fully equipped. You can easily cook for the whole family there.

The outdoor area is the highlight of this Airbnb. There is a private heated pool with a spa, surrounded by palm trees. You will also find beach chairs by the water and a tiki bar style dining area. What an idyllic setting!

Click here to see the latest prices.

Chic on the Beach Side B

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This beautiful villa on Anna Maria Island is perfect for visitors who want to stay in a chic and cute house.

As you get there, you will discover a beautiful blue beach house and the interior won’t disappoint! It was beautifully decorated with stunning materials and high-quality furniture. There is a lot of natural light which is very pleasant.

At the back, you can find a fenced garden with a private pool and a dining table.

There are two bedrooms as well as 2 bathrooms. This would be the ideal property for 2 couples on a relaxing retreat. You can share the common areas while keeping your privacy with your own room and bathroom.

Each bathroom has both a bathtub and a walk-in shower.

Click here to see the latest prices.

Secluded Cottage near Bean Point

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This cute cottage is located in Bean Point (northern end of the island). This is very convenient as you can easily walk to both the Gulf Coast and Anna Maria City Pier.

It’s a great place for a small family as there are two bedrooms and one of them has two single beds. The kitchen is fully equipped so you can cook there or choose to use the barbecue in the garden.

Speaking of the garden, that’s where you will find the pool! There are also some beach chairs there so grab a book and go work on your tan!

It’s also a great option if you are looking for a dog-friendly Airbnb on Anna Maria Island. The hosts accept dogs but you need to let them know in advance as a fee applies.

Click here to see the latest prices.

Lazy Palm Cottage

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This cute cottage is located in Holmes Beach (near the bridge). It’s a great option if you want to be within walking distance of everything. You only need to walk a few minutes to get to the beach, the shops, restaurants and the free trolley to Anna Maria Island.

With 3 bedrooms, this Airbnb can accommodate up to 6 guests. You will find a king bed in the master bedroom, a queen bed in the second bedroom and bunk beds in the last one. This is a good set up for a family with kids. The house decor is pretty simple but you will find everything you need.

The true highlight of the property is located at the back: the garden! This is a true tropical paradise. Palmtrees, swimming pool… you name it! You will enjoy spending quite a bit of time there.

Click here to see the latest prices.

Blue Heron Cottage

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If you are looking for a more secluded cottage on Anna Maria Island, this would be a great option for you. It’s located at the northern end of the island. It’s a quieter area and the private outdoor space is quite spacious. Of course, as anywhere else on the island, you will have neighbours but it doesn’t feel as crowded as most places. You will also be within walking distance to the beach and the main attractions.

The cottage has 2 bedrooms and can sleep up to 4 guests, making it a great getaway for couples or a small family.

The patio is spacious, lush and very pleasant. You will love reading a book and relax here.

Click here to see the latest prices.

Anna Maria Island House Private Pool

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Located in Holmes Beach, on the gulf coast, this Airbnb is great for families who want to get the best of both worlds. It’s a quiet neighbourhood that is ideally situated near the bars, restaurants and ice cream parlors. You can also easily reach the trolley stop.

There is a Publix nearby, making it easy for grocery shopping.

The house itself is very well equipped and you will enjoy spending time there. The garden boasts a wonderful swimming pool as well as a beach shack with a seating area. This is a great place to spend your afternoons. The kids can play in the pool while you relax and work on your tan (and still keeping an eye on them). Also, you will notice there are some turtle drawings in the pool. That’s always a winner with kids!

There are 3 bedrooms and 2 bathrooms. Altogether it can accommodate up to 6 people.

Click here to see the latest prices.

Shore Beats Work

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This gorgeous house is the ultimate luxury Airbnb on Anna Maria Island. Unlike the other properties listed, this one has two storeys plus a garage.

The outside walls are pastel pink which is a bit unusual and beautiful! At the back, you will discover a fenced garden with private pool and beach chairs.

There are 3 bedrooms and 2 bathrooms. It can sleep up to 8 guests which is perfect for large families.

In terms of amenities, there is everything you may need including a fully equipped kitchen, TV, AC and laundry room.

You will also find terraces upstairs. Those a great place to sit down for dinner or breakfast.

Click here to see the latest prices.

50 Steps to Beach

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Looking for a pet-friendly Airbnb near Anna Maria Island? This one is for you!

Located in Bradenton Beach, this cottage can sleep up to 4 guests. It’s a great option for a couple or a small family.

It was beautifully decorated. Whether it’s the paint, the tiles or the furniture, it’s all so beautiful and modern. The kitchen is very well equipped so you can easily cook everything you want here. There also is a barbecue outside.

At the back, you will discover a cute garden with plants (including palm trees of course) and a hot tub!

In terms of proximity to the beach, this is as good as it can get. You’re only a few steps away. It is a very romantic place so if you are a couple looking for a romantic getaway in Florida, look no further.

Click here to see the latest prices.

Walk to the beach

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This Airbnb is located in Bradenton Beach which is very close to Anna Maria Island but not exactly on the island.

The apartment has 2 bedrooms and can sleep up to 6 guests. It’s a great place for families. If you have a dog, you will be happy to know that it is a dog-friendly Airbnb however you need to let the hosts know beforehand.

The apartment is fully equipped. The amenities include Cable TV, a dryer, free parking and a washing machine.

The property itself is everything you expect a Florida house to be like. The outside walls are pastel blue (very pretty) and the home decor features a beautiful contemporary style with beach vibes.

Click here to see the latest prices.

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