Charity De Souza is a Florida native and travel enthusiast. Traveling to over 50 countries abroad and residing in 6, she has a passion for exploring new cultures. While Central Florida is where she calls home, her favorite travel memories include skydiving in Switzerland and watching the sunset in Morocco.
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Pavlo has been working as a travel writer for more than 8 years, and his work has been featured in CNN Travel, BBC Travel, Time Out and Fodor's, among others. Changing cities and continents is a lifestyle for Pavlo, he has been to more than 40 countries across the globe. He can’t get enough of exploring the world and loves to share this passion through travel writing.
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Anna Maria Island is one of Florida’s top beach destinations, beloved by locals and visitors alike for its white sandy shoreline and laid-back vibes. Ready to plan a beach getaway on this seven-mile-long slice of paradise? We’ve compiled a list of the best Airbnb and Vrbo vacation rentals on Anna Maria Island, offering luxurious perks such as private pools and beachfront locales.
Located in Holmes Beach, this charming 1930s cottage is just steps from the picture-perfect beach. The three-bedroom property has enough room for your whole gang to stretch out, offering several living areas that lead to a covered area in the backyard with a pool, seating area and chaise loungers. Other perks include a fully-equipped kitchen with a coffeemaker, flat-screen TVs and a master bedroom with a king-size bed.
Ami Skyview is in a league of its own when it comes to beachfront vacation rentals on Anna Maria Island. It’s not common to stay directly on the sand with an outdoor terrace so close to the water that you can both hear and touch the waves. Add the availability of kayaks, paddle boards, and bicycles for free (!) and it’s a superb choice for your next Gulf outing. The house has a strong Old Florida character, comes with 3 bedrooms, and can accommodate up to 9 guests. You can expect breathtaking Tampa Bay views at any moment of your stay. Also, guests reported seeing dolphins straight from the terrace so there will be some wildlife magic too. The rule is simple here. If you see that Ami Skyview is free for the dates you’re planning to come, don’t hesitate to book.
Usually, private beaches can only be found at the resorts. Well, this amazing Anna Maria Island rental begs to differ. Occupying a picturesque stretch in the quieter northern part of the island, it is among the most striking properties to book. The house is modern and big, with a whopping number of 5 bedrooms and breathtaking water vistas throughout. There’s a pretty backyard pool with a dining patio and a BBQ perfectly suited for all the outdoor fun. But it’s the grounds that take the cake – you’re getting your private chunk of Tampa Bay perfection, palm trees, grass, and sands ensued. Dock access is a delight for boating enthusiasts and the hammock outside is a dreamy feature.
The pool area of this Airbnb looks like a tropical dream. It is sure to become your favorite private oasis surrounded by Gulf Coast greenery. As for the house, it’s a three-story property with 4 bedrooms and 3 bathrooms. The bay is just across the street and you can easily reach all the beaches by car. Plenty of space, a fully stocked kitchen, and relaxing outdoor porches will make your holiday even more fulfilling. This is one of the best Anna Maria Island beach rentals for big families. Kids will have a blast playing in the courtyard, fishing on the small beach nearby, and splashing in the pool with a hot tub.
Reviews are extremely positive at this charming beach house with an Old Florida feel. Guests noted the cleanliness of the property, the supply of beach items like towels, chairs, and umbrellas, as well as the superb location across the street from the surf. There’s a fully stocked kitchen inside, an outdoor patio, and a living room with a sofa. Other big advantages of this Airbnb are fair pricing and proximity to Bradenton restaurants. The street parking is complimentary and there’s a free island trolley nearby to explore the rest of Anna Maria.
Families and groups will love this gem among beach rentals on Anna Maria Island. Four bedrooms provide lots of space, the location directly on the beach is unbeatable, and you will have a private heated pool with a hot tub for scenic lounging. The property is dog-friendly so you can bring furry friends to enjoy the white Florida sands too. The setting is as gorgeous as it gets on Anna Maria – you will have obstructed water views from the floor-to-ceiling windows and outdoor decks to duly enjoy the Gulf of Mexico breeze.
You can live the island life at this charming three-bedroom cottage, which embodies the charm of Old Florida. Its private saltwater pool and close proximity to the beach are its biggest highlights, as you can start your mornings here with a quiet stroll along the shore before hopping on the nearby island trolley. It boasts an open floor plan and air conditioning to keep you cool all summer, while flat-screen TVs and free Wi-Fi keep you entertained. Even dogs are welcome for a small fee.
Casa Azul is a family-friendly Airbnb with 5-star perks, including its location just 600 steps from the Gulf of Mexico. The three-bedroom space has designer furnishings and a chef’s kitchen, while outdoors you’ll find a free-form heated pool with a tiki bar, outdoor shower and grill with al fresco dining. Take in sunset views from one of the several balconies, then visit some of the island’s top restaurants within walking distance.
It will be tough to peel yourself away from the backyard oasis at the Sassy Seahorse, a 2-bedroom Airbnb just 3-4 blocks from the white sands at Bean Point. Take a dip in the glass-tiled pool or enjoy a soak in the spa, then bask in the sunshine on a sun lounger or retreat indoors to enjoy the home’s cozy and colorfully decorated spaces. When you’re ready to explore, some of the best shops and restaurants are nearby in the North end of the island.
You can bring the whole gang for a beach vacation in this Vrbo, which offers large living space and four bedrooms. It boasts a heated pool, covered patio and multiple balconies – but its biggest perk is its prime location just 3 minutes from the white sand beach. Other perks include a fully stocked kitchen, high-speed Wi-Fi and kids will love the Playstation 3. If you want to explore Anna Maria’s attractions, a trolley stop is just 1 minute away.
Not every vacation rental on Anna Maria Island comes with a private rooftop deck. This beach house boasts a fantastic one. You’re guaranteed to spend many inspiring moments watching the sunset and the rolling waves of the Gulf from there. But wait until you see the gorgeous backyard with a lagoon-shaped pool with a hot tub that adds glamor to the experience. 6 guests can comfortably stay at the Airbnb, there’s a fully equipped kitchen for cooking local seafood, and a porched terrace for more outdoor space. It’s a dog-friendly property too.
If you’re choosing to be as close as possible to the beach, this bungalow is an ideal pick for you. With bright designs inside, a fully equipped kitchen, and a space for 4 people, the Airbnb is among the best beach rentals on Anna Maria Island that won’t break your budget. It’s part of a family-friendly condo complex and you will have access to a communal pool as a perk. As for the beach, there’s no need to cross any streets or deal with traffic, the house is situated right on the sand so the surf is literally your backyard. There’s also a snug outdoor patio for sunset dining or wine sipping.
You can’t get any closer to the Gulf than this luxury abode in Anna Maria Island, which sits directly on the sugar-white sands. Accommodating up to 6 guests, the 3-bedroom home boasts an expansive deck with a gas grill and heated pool with plenty of sun loungers. Best of all, indoors you’ll find cozy rooms with beach views where you can fall asleep to the sound of crashing waves. In addition, there are miles of beautiful beach to stroll and collect colorful seashells, while numerous shops and restaurants are just a stone’s throw away.
This Anna Maria Island Vrbo is an oasis of tranquility, featuring a heated saltwater pool just 200 steps from the beach. The two-bedroom property boasts a large living room for hanging out, while its outdoor area boasts lush landscaping surrounded by mature palm trees. Kids will love the games available, such as corn hole, while its location is convenient for exploring more of the island. Everything is within walking distance or you can access attractions via the free Trolley, and there are even beach bikes if you want to sightsee on two wheels.
This Holmes Beach Vrbo is a two-minute walk to the beach and offers a private heated pool and large covered lanai. Step inside to discover an open floor plan with plenty of light-filled space and coastal decor, then enjoy a meal on the front outdoor deck or enjoy the backyard oasis with a gas grill and shallow pool area for little ones. The hosts provide everything you need for a memorable beach vacation, including towels, chairs, umbrellas and a cooler bag.
Those who seek romance will find it here. This beachfront rental is an ideal choice for 2 and comes with a snug panoramic patio, atmospheric wooden interiors inside, and an outdoor pool in the backyard. It’s also among the best-reviewed properties in Anna Maria so you’re in good hands. People loved the proximity to the water on one hand and the impeccable sense of privacy on the other. That’s a perfect mix if you’re looking for a romantic break with your significant other. The location is also good for visiting restaurants and trying the mouthwatering local seafood dishes.