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Anna Maria Island is Calling Your Name!

Island Real Estate is Anna Maria Island’s leading full-service real estate agency and property management company, specializing in waterfront properties, rentals, investment property, beach homes, island homes and more. These accommodations are dispersed throughout the three cities of Anna Maria Island -- Anna Maria City, Holmes Beach and Bradenton Beach. Whether you're seeking a getaway in a beach home, quaint cottage, or a luxurious Gulf Front private home or condo, Island Real Estate has the perfect rental for you! Start planning your island escape today!

  • Wifi
  • Restaurant Onsite
  • Pets Allowed
  • Property Size 251 units
  • Conference Facility
  • Kids Allowed
  • Nearby City Tampa
  • Nearby Water Gulf of Mexico
  • Open Dates All Year


The smooth white sands of Anna Maria's beaches cannot be beat. Stretching from the northernmost tip of the island, through Anna Maria, Florida and continuing down into Holmes Beach, finding a piece of sand and a view cannot get any easier! From private, condo-front beaches to public beach parties and fun, there's something for everyone on Anna Maria Island.


Island Real Estate has a variety of properties to fit your family, from cozy condos to lavish beachfront homes. Although you can choose your perfect home away from home, you will want to spend most of your time under the sun. Relax on Bradenton Beach for an afternoon, take out Anna Maria Fishing Charters for some fun, or show the kids the Manatee County Audubon Society. There is nothing but fun here!


When you're in Florida, it would be a shame not to hit the links. Tee off while you're staying at Island Real Estate at Anna Maria Island! The staff will be happy to help find a course that will meet all of your needs. From beginner to expert, you'll have the golfing vacation of a lifetime.


Plan your next Florida family reunion at Island Real Estate and your group will be requesting a return trip year-after-year. Luxurious accommodations offer a bevy of amenities to keep everyone in your group satisfied including full kitchens, flat screen televisions with cable/satelite, private balconies and decks, and easy access to the beach. There are a ton a great places to shop for unique items on Anna Maria Island, or you can head to the Historical Society Museum to learn more about the area. Bring the entire extended family for a fun-filled reunion with Island Real Estate!


There are plenty of great ways to explore Anna Maria Island during your next trip to Florida with Island Real Estate. Head to Leffis Key to experience one of the area's most unique natural features. Boardwalk trails allow you to explore the salt marsh lagoons while you take part in some of the island's best bird watching. You can also check out some of the local parks and preserves, allowing you to experience the beauty of Manatee County at your own pace.


The fishing off the coast of Florida is some of the best in the country. Visitors can enjoy everything it has to offer with Anna Maria Fishing Charters. Let the locals show you where to cast your line for a chance at a trophy catch. Pack up your tackle box for the adventure of a lifetime!


Imagine walking hand in hand with the person you love on the white sands of the Florida coast. What better place to reconnect and enjoy each other's company while you explore? Spend the day on the beach, take out a fishing charter, or get dressed up for a night on the town with local music and cuisine. Reignite the spark!

Pet Friendly

Tired of that guilty feeling you get whenever you leave Fido at home? Well, leave that guilt behind and head to Anna Maria Island, where Island Real Estate offers pet-friendly accommodations. Just make sure to let Island Real Estate know that Fido will be coming along, as not all rental properties allow pets.


When you're in Florida, take time out of your trip to learn about the local environment. Go on the beach and pick up some trash, you'll feel better once you do. Visit a local nature preserve. Leave the place a better place when you've left than when you arrived. Book your trip today!


Island Real Estate prides itself on their hand selected properties that exude luxury at every turn. Enjoy waking up in a plush king-sized bed and washing up in a state-of-the-art bath. Experiment in the full gourmet kitchen, relax on the deck overlooking the beach, or enjoy curling up in front of the fireplace. Each abode has a unique decor and amenities, so choose what suits you best. Let them cater to you!


Spend your honeymoon on white sandy shores and in a beautiful vacation rental with Island Real Estate. You can choose a cozy beachfront home with a full kitchen, king-sized bed, and a few minutes drive to all that the area has to offer. Dig into decadent sea food paired with live music while you dance away the night! There is no better way to start your lives together!

Cabins, Cottages, and Chalets

Overnight accommodations at Island Real Estate consist of an inventory of over 200 hand-picked rental properties, ranging from condos to private homes and cottages. Many options boast great views of the Gulf, as well as direct beach access -- allowing vacationers to experience their own piece of "paradise." Pet-friendly and luxury accommodation options are also available.


Your house might not be big enough to fit the whole family. Why not find a vacation rental that does so that the whole family can join in the holiday fun? Spend quality time creating a holiday feast in a full kitchen, relax in the sun on the beach, or take the kids out fishing for the first time. Weather will not get in your way as you make memories for a lifetime!


Escape to the small town of Anna Maria, Florida, located on the northern end of Anna Maria Island, which boasts relaxing sunsets, top-notch eateries, and sugary white-sand beaches as far as the eye can see. Enjoy an unforgettable end to each day while strolling from your rental home down the beach, followed by a stop in one of the area's beachfront eateries. The name says it all!

Villas and Condos

Whether you're looking for a quaint condo that's perfect for a romantic rendezvous or a sprawling vacation home for your entire family, Island Real Estate has a vacation rental that suits all of your travel needs. Many of these condos offer access to resort amenities including swimming pools, fitness centers, and more. You'll also find full kitchens, spacious living areas, private balconies and more, all designed to give you an unforgettable Anna Maria Island getaway. Start planning your trip today.

  • Swimming Pool
  • Air Conditioning
  • Alarm Clock
  • Balcony
  • Coffee Maker
  • Full Kitchen
  • Jacuzzi
  • Microwave
  • Patio
  • Refrigerator
  • Live Entertainment
  • Photography
  • Shopping
  • Sightseeing
  • Swimming
  • Theme Parks
  • Volleyball
  • Beach
  • Bird Watching
  • Boating & Watercraft
  • Outdoor Grill(s)
  • Marina
  • Wildlife & Nature
  • Sailing
  • Saltwater Fishing
  • Fitness Programs
  • Laundry Facilities
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Nearest Airports

  • Sarasota Bradenton International Airport (SRQ) / 12.8 miles
  • St Petersburg Clearwater International Airport (PIE) / 27.6 miles
  • Tampa International Airport (TPA) / 33.9 miles

* Not all airports listed here may be open to public use, or service commercial flights

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This property is ranked number 2 on Top Florida Luxury Getaways. Read about it here.