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13 Vacation Rentals on Anna Maria Island

Victoria Green

If you haven’t stayed in any vacation rentals on Anna Maria Island in Florida, you’re missing out!

This stunning destination features an impressive 7-mile stretch of pristine beaches. Here are the top 13 places to stay on your next vacation.

Booking the flights and coordinating dates with the rest of the travel group is stressful enough! Add in finding the perfect accommodation, and you’ve got a busy few hours (or more!) of planning.

Our list of Anna Maria Island vacation spots will take away the hotel hunt and leave you with options for stunning stays. 

Ready for a getaway filled with endless beaches, fun shopping opportunities, fantastic restaurants, and great bars? Then you need to book a trip to Anna Maria Island!

Editors’ Picks: Best Rentals on Anna Maria Island

Breathtaking Beach House

Tropical-themed vacation rental in Anna Maria Island, FL
This tropical themed beach house is one of the top vacation rentals on Anna Maria Island – Photo courtesy of VRBO

We’re starting with this incredible stay that offers direct beach access and incredible views of the nearby gulf! This beachy paradise is one of the top vacation rentals on Anna Maria Island because of its proximity to Manatee Public Beach and Bradenton Beach.

This spacious cottage can fit up to five people, making it an excellent spot for a girls’ weekend or a family vacation. While there are many restaurants available around this VRBO, there’s also a full kitchen that you can use to whip up a few meals during your stay.

One unique feature of this stay is the proximity to the free trolley that travels around the whole island. Head down the street for about one block, and you can catch the trolley and skip any parking snafus.

Guests love watching the sunrise over the beach from the private deck. This spot is nearby various seafood restaurants that have tasty options. You’ll want to give them a try!

Bradenton Beach Condo With Pool

Bradenton Beach Condo With Pool  for Rent in Anna Maria Island, FL
Can’t decide between a heated pool or a vacation by the beach? This incredible vacation rental on Anna Maria Island provides both! – Photo courtesy of VRBO

Can’t decide between a heated pool or a vacation by the beach? This incredible beach oasis provides both! That’s why we needed to include it as one of the best Anna Maria Island rentals.

This cozy condo features multiple TVs, a dining room, a full kitchen, air conditioning, and a washer-dryer combo making it easy to stay in on the occasion that the weather is not cooperating. A BBQ is ready to be fired up for some tasty grilled dinners outside.

This beach condo is perfect for those who want to spend time exploring Anna Maria Island in between hours at Bradenton or Coquina Beach. It’s close to art galleries, museums, and a local theater, in addition to the historic Bridge Street.

Reviewers love how the property is surrounded by tropical plants, making it feel like you’re on a remote island destination.

Intracoastal Waterway Vacation Rental on Anna Maria

An updated modern Condo rental in Anna Maria Island Florida
Photo courtesy of VRBO

This incredible condo features views of the gulf coast and the bay. This is one of the top vacation rentals on Anna Maria Island for those seeking a short or long-term stay.

This updated modern condo offers amenities like covered parking and access to a dock. Take advantage of the dock access by kayaking, paddle boarding, or fishing here.

One of the best parts about this condo is its location right by the beach – you’re only a few steps away from digging your toes into the sand. Enjoy the old Florida charm of Anna Maria Island and its stunning sunsets as you stroll along the nearby beaches.

Guests love the cleanliness of this condo and rave about the friendly customer service! Many have noted how impressive the sunrises are from the condo balcony.

Brightly Colored Anna Maria Island Getaway

Brightly colored rental home in Anna Maria Island, FL
Photo courtesy of VRBO

This whimsical house has been rated number 15 out of 260 for the top-rated vacation rentals on Anna Maria Island by the biggest real estate company on the island. One look at the brightly-colored outside, many amenities, and fun interior décor, and it’s easy to see why!

This getaway has a pool, hot tub, and even a covered hut with seating to take a break from the sun! A game room featuring books, movies, and games awaits you for the occasional rainy days.

There is so much to do at this property that you won’t want to leave! Volleyball in the pool, air hockey in the game room, and lounge chairs by the pool are only a few things to enjoy at the house.

Reviewers love how close this property is to the beaches, shops, and Anna Maria City Pier – they’re only a few minutes away! Many guests booked their next stay at this stunning house as soon as they got home (or even before they left).

Beautiful Holmes Beach Condo

Beautiful Holmes Beach Condo in Anna Maria Island, Florida
Photo courtesy of VRBO

With the many positive reviews and happy guests, it wouldn’t be right to leave this off our top Anna Maria Island vacation rentals list! There are quite a few activities available nearby this rental at Holmes Beach, including swimming, sailing, windsurfing, shopping, and more.

Next door to this villa-style condo is a local café that serves delicious food all day long. At night, you can head to this café for live music. 

Take advantage of the full kitchen and grill if you feel like staying in. There’s even a heated swimming pool on the property to lounge in after exploring Anna Maria Island.

Reviewers recommend walking a few steps to the nearby beaches (Manatee Beach and Bradenton Beach) and enjoying the views, picnic tables, grills, and soft sand at Holmes Beach. It’s the perfect spot for visiting families who want an island getaway.

Newly Renovated Holmes Beach Duplex

Comfortable living room of a newly renovated beach house in Anna Maria Island, FL
Photo courtesy of VRBO

This stunning duplex is recently renovated and features modern, beachy vibes with cool accent pieces that will make any traveler feel like they’re in a duplex photo shoot. You’ll be happy to know everything from the kitchen to the flooring was updated.

You’ll find this charming duplex rental in a quiet neighborhood, making it easy to have a tranquil vacation. Enjoy the fenced-in backyard by sitting on the patio as you grill up dinner.

This stay is perfect for families – especially those with dogs, as it’s even pet-friendly. Guests love the short walk to Holmes Beach. This pathway leads to a quieter section, so you’ll feel like you’re on a private island!

Stunning House on Anna Maria Island Near Gulf of Mexico

A charming beach house for rent in Anna Maria Island,Fl
Photo courtesy of VRBO

This charming house features a fun, bright, and modern décor on the inside and is recognizable by its blue exterior. This cozy home is ideal for couples, families, and vacations with friends.

Bradenton Beach is a few short steps away from this house. You can also enjoy the Gulf of Mexico However, you can enjoy the spectacular sunset right from the front yard!

The backyard features a shared pool area that’s heated in the wintertime. Chat with the other renters or head to the community center across the street for a game of shuffleboard.

Guests love the walkability of the neighborhood and the peacefulness of staying in a residential area.

Pet-Friendly Ilexhurst Cottage

Pet friendly beach cottage in Anna Maria Island, Florida
Photo courtesy of VRBO

Featuring two bedrooms and the ability to hold up to six people, this is one of the most outstanding vacation rentals on Anna Maria Island for a relaxing girls’ trip! This beachy cottage has everything you need to make you feel like you’re in paradise.

The backyard has a stunning saltwater pool ready to swim in, a tiki bar, and an area to swing in a hammock. They take their sunsets seriously here with a special viewing area set up.

Stock up on fun drinks at the nearby shopping center. Don’t forget to turn up the tunes as you lounge in the pool and fire up the grill! If you want to spend your day at the beach, it’s just a short walk away.

The stunning backyard area has previous guests rebooking a stay here repeatedly.

Resort Condo on Bradenton Beach

Tortuga Inn condo unit for rent in Anna Maria Island, FL
Photo courtesy of VRBO

Staying at this Tortuga Inn condo is the perfect way to see what everyday life is like for the locals for a few days. This accommodation is found in a resort that has excellent amenities like access to two pools, covered parking, chairs, and umbrellas to use for beach days.

The bay and ocean views from the balcony are unbeatable at this vacation home. Head down to the picturesque private beach for potential glimpses of manatees and dolphins swimming.

At the pergola, you can rent boats or jet skis. Or, bring your own! As a heads up, you’ll need access to the condo owner’s boat slip for this option.

Guests note that the kitchen is always well-stocked, and the condo is super clean. Plus, you’re on the top floor so that you can enjoy quiet evenings during your stay instead of worrying about loud neighbors.

Quiet, Remodeled Holmes Beach Cottage

Living room of an adorable beach cottage for rent in Anna Maria Island, FL
Photo courtesy of VRBO

Staying at this duplex will make you feel at home with its cute décor and cozy feel. With all new appliances, flooring, and kitchen, you’ll be prepped to enjoy one of the best vacation rentals on Anna Maria Island.

This adorable beach cottage has everything you need – including beach towels, chairs, an umbrella, and a cart. The outside patio is a perfect way to enjoy the island weather with a gas grill and plenty of seating to hang out on.

There are even cute hammock swings that visitors can lounge in under the shade of the roof. Guests are enjoying the décor and giant king-size bed available. There’s also a 60-inch smart tv available for use.

Anna Maria Village Cottage

Charming vacation rental cottage in Anna Maria Island, FL
Photo courtesy of VRBO

Access this stunning cottage by the adorable stone pathway that weaves through wooden beach chairs. The back-covered porch features padded seats for relaxing in. Keep walking to the backyard, and you’ll find super comfortable lounge chairs with an optional umbrella cover.

Hop on the free Anna Maria Island trolley to access the nearby shops and restaurants. Or walk to the community center for additional activities. A few minutes away are multiple parks ready to explore. Bean Point Beach is just 0.2 miles from this accommodation.

Former guests love how well-stocked this vacation site is! The off-street parking and pet-friendly policy make this an excellent stay for individuals, couples, and families looking for a quiet stay.

Cozy Cottage on Northern Section of Anna Maria Island

Anna Maria Island cozy cottage for rent
Photo courtesy of VRBO

This fun, beach-themed cottage holds up to four people and is a short walk away from the stunning Gulf Beach. As far as vacation rentals on Anna Maria Island go, it is one of our favorites because of how cozy and homey it feels.

A lovely deck with a gas grill is a great way to enjoy the company of family and friends while staying at this cottage. Multiple restaurants are within walking distance of the cottage, along with museums, waterparks, and plenty of watersport options.

Just a warning, there is a shared laundry area, so you may need to wait your turn for washing and drying clothing loads.

Guests love how little details in the decorations make you feel like you’re staying in a home away from home. There are plenty of spaces to cozy up inside with family members or significant others.

Idyllic Anna Maria Cottage

Beautiful beach bungalow for rent in Anna Maria Island, Fl
Photo courtesy of VRBO

Bring your whole family or a group of your close friends to this beautiful beach bungalow. The interior of the house is cozy and comfortable. The exterior is stunning and offers a heated pool with your very own waterfall surrounded by lounge chairs and a dining area.

Take 200 steps, and you’re at the beach so you can search for pretty seashells or swim in the blue waters. While you’ll likely be spending all your time at the private pool or beach, free WiFi is available, along with an impressive three TVs in the home.

Pine Avenue is only a short trolley ride away and offers those passionate about shopping fun boutiques to explore. There are multiple private parking spots available, and we know you won’t need to drive until check out once you park! Local restaurants are only a short walk from the cottage, and other activities are accessible by the local trolley.

Reviewers note how close the cottage is to everything – the beach, restaurants, and activities. Enjoy a family vacation here, or bring your significant other for a quiet island getaway.

Vacation Rental Properties s on Anna Maria Island

These Anna Maria Island vacation rentals are perfect for enjoying the many white sand beaches, turquoise waters, and delicious local food. 

Spend a romantic weekend at a peaceful, residential getaway or get together and jam to music with friends nearby heated pools. 

Whatever your ideal vacation stay is, you’ll be able to find your perfect VRBO rental on this list!

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