The Best Family-Friendly Rentals on Anna Maria Island

When you’re considering a getaway destination with your family, it can be hard to narrow down a location. You want somewhere with a little bit of everything since your group is sure to have varied ideas of fun. You’ll want to go to a destination that encourages you to put your phones down and spend some much-needed quality time together. Plus, it would be a bonus if that particular destination didn’t break the bank.

Enter Anna Maria Island, a stunning barrier island just off the Gulf coast of Florida. This destination maintains that “Old Florida” feeling that so many other locations have abandoned, providing a slow-paced atmosphere you’re sure to appreciate. But slow-paced doesn’t mean boring! There’s plenty to do, from shopping and dining to water sports, museums, and more. While you’re in town, here are some of the best Anna Maria Island vacation rentals that can fit your entire crew! 

kids on anna maria island beach

Ocean Breeze

This 4-bed, 3-bath home sleeps up to 8 people and is a quaint yet luxurious property in the heart of Holmes Beach. Staying in this elevated private duplex will put you just a five-minute walk away from the most breathtaking Gulf beaches, perfect for enjoying the Florida sunshine. Back at home, you’ll find a whole host of features that are sure to impress. The professional décor will help you feel right at home, the fully stocked kitchen makes it easy to prepare meals, and the bonus rec room is the perfect place to get competitive with foosball. Step out back to take a dip in the private heated pool with spa, all surrounded by lush and inviting tropical landscaping. 

Sea Horse Beach House

If you have a slightly bigger family, consider this 4-bed, 3-bath home that can sleep up to 10 guests. This home is situated on the southern end of the island in Bradenton Beach, just a short walk away to the shops and restaurants of Historic Bridge Street. Plus, you’re literally a 30-second walk away from the Gulf beaches! Your home also comes with all kinds of convenient amenities to keep you in luxury for your entire stay. You can take care of the family’s laundry in your in-home washer and dryer, sit on your rooftop deck to enjoy the view of the Gulf, or enjoy a movie on one of the home’s 5 HDTVs! In your backyard, you’ll be able to soak in your private heated pool or enjoy the covered poolside lanai for the ultimate relaxing evening.

Cabana Breeze

Families of 8 are sure to enjoy this incredible 4-bed, 2-bath property. You’ll find this home in the city of Anna Maria on the northernmost side of the island. This area is quiet and relaxing while still being just a short walk away from the popular Pine Avenue and the Anna Maria Island City Pier. During your time at home, you can find all kinds of convenient beach equipment to take to the shores with you, including bikes, a beach wagon, chairs, games, and more. Inside, you’ll love having a flat screen TV in every bedroom as well as an XBOX gaming system! One of the best features of this home is the brand-new rec room and poolside cabana, sure to result in afternoons of unlimited fun.

Waterside House

Waterside House is a beautiful property in Bradenton Beach that can suit 10 people between its 4 bedrooms and 5.5 bathrooms. If you’re searching for a truly luxurious property, look no further! Of course, the location is incredible, putting you just minutes away from the island’s best attractions. But with so many amazing features at home, you might find it hard to leave! Enjoy the large garage for keeping your car safe, then head inside to enjoy the rest of the newly renovated property. You’ll fall in love with the professional décor and can take advantage of the fully stocked kitchen and new flat screen TVs. Take the elevator between floors or up to your top deck, giving breathtaking views of the area. Three balconies invite you to spend your time outdoors, or you can take a drip in your heated private pool with Bay views. 

anna maria island vacation rental

Aqua Bay

Located in central Holmes Beach, this property can suit up to 8 people thanks to its 4 bedrooms and 3 bathrooms. This newly constructed home is ideal for those who want to spend their time on the water, since it’s situated right on the canal and has its very own private boat dock! Inside, enjoy luxurious features like hardwood floors, professional décor, and stainless-steel appliances in your fully equipped kitchen. Outside, enjoy a drink on your rooftop deck and fire pit, go for a swim in your private heated pool with spa, or enjoy the covered open-air balcony that overlooks both the pool and the canal. When you’re ready to head to the shore, load up your complimentary beach cart and take the short 5-minute walk to the sand.

Pineapple Key

Pineapple Key has just recently been renovated, and you know we’ve spared no expense to give you the most luxurious experience possible! This Holmes Beach property features 4 bedrooms and 2 bathrooms, ideal for up to 8 guests. Throughout the home, you’ll find breathtaking features like the new Travertine floors, updated trims and molding, and granite countertops. Relax in one of your two living areas or in front of one of your six TVs. Get competitive with your pool table or Wii gaming system, or walk just two blocks to the beach! When it’s time to head out into town, this home is just two houses away from an Anna Maria Island trolley stop, giving you a convenient and free way to get around the island.

anna maria island vacation rental

Ocean Walk

For bigger families, Ocean Walk offers plenty of room. This 4-bed, 3.5-bath home is suitable for up to 12 people. This is one of our newer vacation rental properties, but its features have already helped it make a name for itself! Just 30 seconds away from the beach, this home offers plenty of amenities, from the high-speed wireless internet and flat screen TVs to the loft, rec room, fully stocked kitchen, and complimentary beach equipment. Head up to the rooftop deck to enjoy a drink while the sun goes down, or relax in your very own private heated pool with spa. This home is located in the city of Anna Maria, offering a secluded and comforting neighborhood for you and your family to enjoy. 

Mango Breeze

Finally, Mango Breeze is an exciting property that can suit up to 8 guests between its 4 bedrooms and 3.5 bathrooms. The beautiful décor both inside and out will have you feeling truly transported to an island paradise! You’re just a one-minute walk from the beaches of Holmes Beach, and we provide plenty of beach chairs, bikes, umbrellas, and beach equipment for your use. We also provide baby items such as high chairs and strollers! You’ll want to spend plenty of time out back if you rent this property; the lush tropical décor surrounds your very own private heated pool, poolside Tiki bar, and games like ping pong and cornhole. Crank up the stereo system, enjoy the game on the outdoor TV, and cook up a meal on the charcoal and gas grill.

So, is one of these beachfront vacation rentals on Anna Maria Island calling your name yet? Still looking for the perfect property for your family? Contact us today so we can help you book your dream getaway to Anna Maria Island!