Best Anna Maria Island Vacation Rentals for Family Reunions

Bringing your family reunions to Anna Maria Island? You all are in for a treat! There is so much to see and do on the shores of AMI, so no matter what your family is interested in it, everyone will have an attraction to explore. But before you can get to the best destinations, you need a place to stay! Luckily, we have tons of rental homes on Anna Maria Island that will suit your family, no matter how many people you’re bringing. Here are a few of our most popular Anna Maria Island cottages for big families, as well as where to eat and what to do while you’re on vacation.

Where to Stay

Exterior of multi level Anna Maria home

Gulfside Oasis

This 6-bedroom, 5-bathroom home in Holmes Beach is perfect for up to 12 people. Take care of everyone’s laundry with two washers and dryers, feed an army in the fully equipped gourmet kitchen, and enjoy a view of the Gulf from any of your multiple balconies. Relax with your family in front of the 60-inch Smart TV in the living room, get competitive at foosball or ping-pong, or take a quick one-minute walk to the beach. The possibilities are endless!

Interior of kitchen with large island in Anna Maria Island

Lighthouse Lagoon

This spacious 5-bed, 4-bath home in the city of Anna Maria is the ultimate in relaxation. This beautifully updated home will have you in the lap of luxury with stunning tropical decor and top-of-the-line fixtures and furnishings. The outside of this home offers beach equipment like bikes and beach chairs, as well as an above-ground hot tub, a lagoon-style pool with a tanning deck, and a swim-up bar with seating. You’re just one minute away from Pine Avenue to get all your shopping done.

Exterior of porch overlooking pool in Anna Maria Island

Absolute Paradise

The name says it all! This 5-bed, 4-bath property in the city of Anna Maria sleeps up to 14 guests and provides something for everyone. Everyone can watch what they please on one of the 8 TVs, or you can try to beat your family members on the Xbox or at darts, cornhole, and board games. Head to the rooftop deck for a stunning view of the water or stroll 2 minutes to the Gulf or to any of the restaurants and shops along Pine Avenue.

Interior of dining room overlooking the ocean in Anna Maria Island

The Blue Horizon

The Blue Horizon is one of our biggest properties, boasting 9 bedrooms and 7.5 bathrooms to suit up to 21 guests. This home is in a prime location in Bradenton Beach and offers multiple panoramic Gulf views for you to enjoy. There are multiple living and dining areas and kitchens for you to feed your whole family, and you can step right onto the beach from your second level beachfront deck! It’s also easy to walk or grab the free Island trolley into town.

Exterior of multilevel yellow house with pool in Anna Maria Island

Tropical Oasis

Located in Anna Maria, this 5-bed, 4-bath home puts you right in the middle of all the action. Enjoy your private heated pool with covered lanai, get all of your luggage to the top floor thanks to the elevator, and step out onto any balcony for an unmatched view. You’re just one minute away from the white sandy beaches as well as the Pine Avenue shops and restaurants. You can also easily reach both the North and South traveling trolley stops to get you anywhere you need to go.

Exterior of pool with large deck in Anna Maria Island

Coastal Horizons

This 6-bed, 4-bath home in Bradenton Beach is perfect for your party of 12. This elevated luxury property has everything you could need, from a convenient elevator to our Professional Linen Service Program that will take care of your towels and bedding. Head outside to enjoy the private heated pool with spa and covered lanai with an outdoor bar, or walk down to the Gulf beaches, historic Bridge Street, or Bradenton Beach Fishing Pier.

Exterior of coral home with palm tress in the front in Anna Maria Island

Coral Retreat

If you’re looking for a truly luxurious property, Coral Retreat is the answer. This 5-bed, 3.5-bath home in Holmes Beach is surrounded by stunning tropical landscaping and will put you in true paradise. Catch up on your favorite show on the Roku TV or try your hand at the arcade games or ping pong. Safely park your car in the two-car garage, then head out back to enjoy your private heated pool with spa, covered lanai with poolside bar, barbecue grill, and a flat-screen TV.

Interior of kitchen and dining room in Anna Maria Island

Tiki Beach

Your party of 12 will love the 6-bed, 5.5-bath home located in Holmes Beach. This is the place to be if you want to spend time on the shore since you’re just a one-minute walk away from the beach! At home, you’ll have stunning views of the water from any of your multiple covered decks, as well as a gourmet kitchen with stainless steel appliances, 8 flat-screen TVs, and wireless internet.  Enjoy your private heated pool and spa outside or take a short 10-minute walk to the eateries and shops on North Anna Maria Island.

Exterior of multilevel home with garage in Anna Maria Island

South Seas

This 6-bedroom, 4.5-bathroom home in Holmes Beach is the perfect place to stay for your family reunion. The big attraction here is the deluxe pool with spa and the incredible water slide to go along with it! It also features like Xbox and Wii game stations, iPod radios in the bedrooms, and a ping pong table. Take a short 3-minute walk to the beach for even more fun in the sun!

Interior of an open floor plan with living, dining room, and kitchen.

Cabana Beach

In this 5-bed, 3.5-bath home in Holmes Beach, your party of 10 will have the ultimate getaway. Let everyone watch what they want on one of the 8 flat-screen TVs, feed the whole family in the professional kitchen with Viking appliances, and enjoy the spacious bedrooms and living areas. Outside, take advantage of the private heated saltwater pool with spa, covered poolside lanai, and beach equipment provided to you. You’re just a two-minute walk away from the beaches and the closest trolley stop. 

anna maria vacations rentals

AMI Life

This 5-bed, 3.5-bath home comfortably sleeps 10 guests. You’ll find tons of amenities in this 3,730-square foot home, such as a Foosball table, XBOX, fully equipped kitchen, and elevator. Step outside for even more fun with your private heated pool, canal, and boat dock, or venture into town for even more fun.

vacation rentals anna maria

Hunters Point

12 guests can stay in this 6-bed, 5.5-bath home. With over 5,000 square feet of pure luxury, this home includes a pool and ping-pong table, solid wood cabinetry, and stainless steel appliances. Outside, you’ll find a deep water boat dock, multiple balconies with gorgeous views of the water, and an oversized heated pool with lights!

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Southern Exposure

As you might guess, this 5-bed, 4.5-bath rental option has incredible views from all throughout. You’re just blocks from Pine Avenue and everything else Anna Maria Island has to offer, and inside, you can enjoy luxurious fixtures, high ceilings, a full kitchen, and more.

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Anna Maria Grand Beach House

One of our largest properties, this 9-bed, 9-bath home in Bradenton Beach provides all you’ll need for a vacation with room for a whopping 28 people! You can experience laundry facilities, a full kitchen, a private heated pool, gaming systems, wireless Internet, and 2 elevators inside this brand new rental. Just moments from the beach, this home will be hard to leave!

beach rentals anna maria island

Casa del Sol

Bring your group of 14 to this 5-bed, 3-bath home for your dream vacation. With plenty of parking and large living spaces, there’s plenty of room for everyone. Take advantage of our fully equipped kitchen and our Professional Linen Service Program, and sail out on your dock or have a drink at the wet bar. 

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Caribbean Dream

This incredible 5-bed, 4.5-bath home is perfect for your group. You’ll find breathtaking views of the Gulf and the Bay, and you’ll be just a couple minutes’ walk from the shore, as well as local shops and restaurants. Back home, experience your heated pool and spa, covered lanai, and more.

anna maria island beach rentals

Antigua Bay

Enjoy the beauty of luxury in this 5-bed, 4-bath home. Inside, you’ll find game tables and arcade offerings, as well as plenty of living space. The true appeal is the outdoor space, where you’ll have access to a private heated pool in the midst of a tropical oasis, as well as a rooftop deck, covered lanai, gas grill, and more.

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Where to Eat

While cooking at home can be fun, you want to eat out sometimes, but if you have a large group, it’s important to make sure the restaurant can accommodate you. Here are three of our favorite restaurants that accommodate large groups and take reservations.

The Waterfront Restaurant is a relaxed and casual eatery that provides a stunning view and mouth-watering dishes. Bring your whole family to sample tasty Florida themed appetizers, then continue on with delicious seafood, a juicy burger, or a delicious selection from their beer and wine menu.

A variety of options to eat on picnic table.

Sharky’s Seagrill in Bradenton Beach boasts “fine dining in a casual atmosphere.” This eatery strikes the perfect balance between upscale and welcoming, and the menu certainly doesn’t compromise. Start with some appetizers and salads, then move on to pasta plates, entrees, and sides featuring the freshest seafood and the best local produce.

If you’re looking for something a bit more upscale, Beach Bistro is an award-winning surfside dining experience right on the Gulf of Mexico. Come sample delicacies like USA prime beef tenderloin, Bistro duckling two ways, and bourbon and maple grilled Gulf Shrimp. They also have a wide selection of soups, salads, and desserts to enjoy.  Don’t worry; they have a kids’ menu as well!

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What to Do

There’s truly something for everyone on Anna Maria Island, so no one has to sacrifice their itinerary. If you’re visiting in the spring, events like local farmer’s markets and Springfest are some activities you just can’t miss. If your vacation is in the summer, be sure to join in on the 4th of July festivities or the Village of the Arts Art Walk Weekend. No matter what time of the year you visit, there are countless family-friendly activities for you to explore!

We hope that your upcoming family reunion brings unforgettable memories and some much-needed quality time with the ones you love most. While you’re planning your getaway, consider one of our Anna Maria Island rentals to call your home away from home. Contact us today to start planning your reunion!

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