Best Anna Maria Island Vacations

Anna Maria Island Destination Overview

Anna Maria Island (Wikipedia) was named the third prettiest city in the country in 2013 by Forbes magazine, so you can be sure that a holiday here will be nothing short of splendid with unbeatable natural views of gorgeous landscaping and sparkling waters. With swaying palm trees and sandy shores, this paradise might have you feeling like you never want to leave.

Anna Maria Island property 361357

This Floridian hidden gem offers visitors 7 miles of beachfront between the mainland state and the Gulf of Mexico. The atmosphere here is certainly one of a laid-back island lifestyle, which is emphasized by friendly locals. This homey isle will keep you totally at ease throughout your stay with its plethora of residential areas and and general peace and quiet.

You'll find excellent dining options all around the island where fresh seafood is sure to be standout. Enjoy adventures out on the water whether it's kayaking or swimming with dolphins, then head inland to explore Anna Maria Island's culture to learn more about the area.

Don't worry about how you'll get around the island to explore the different attractions and experience the various activities - there's the free trolley service that travels around the whole of the island between 6 a.m. and 10:30 p.m.

Anna Maria Island property 361357
Anna Maria Island rental property # 361357

When to Visit Anna Maria Island

Anna Maria Island experiences a climate typical of the west coast of Florida. The annual average temperature is around 75 degrees Fahrenheit with winters ranging from the 50s to the 70s and summers from the 70s to the 90s.

With this tropical feel, you might want to escape the cold, snow and dreariness of the winter months and soak up some sun and vitamin D. Trade your boots and coats for flip flops and swimsuits in December or January. Anna Maria Island is also a lovely spot for spring break with its miles of beaches and family-friendly attractions.

Learn more about Anna Maria Island weather >>

Anna Maria Island property 439787vb
Anna Maria Island rental property # 439787vb

What to Do on Anna Maria Island

  • Anna Maria Beach: With 7 miles of shoreline, you'll certainly want to spend lots of time at the beach, and Anna Maria Beach is an excellent option. Here you'll find peace and tranquility, making it an idyllic spot to relax. Once you find that perfect spot for your beach towel, you can catch up on reading or taking a refreshing dip. Other great options include Manatee Public Beach, Coquina Beach, Whitney Beach and Treasure Island Beach; see images.

  • Anna Maria Bayfront Park: Take in the stunning natural beauty from the sandy shores to the sparkling waters, lush, tropical landscaping and picturesque scenery while enjoying time with loved ones at this seaside haven. The park offers grills, pavilions and picnic tables, so you can have a tasty meal outdoors. Playground are on premises to keep kids occupied; see images.

  • Anna Maria Island Historical Society: Explore the history and culture of the isle at the Anna Maria Island Historical Society Museum. You'll discover information on the locale's first settlers, characters through time and even the city's original jail. Take a tour of the cottage that sat on City Pier, or join in on a kid-friendly scavenger hunt; visit website.

Where to Eat on Anna Maria Island

  • Sandbar Restaurant: If you're looking for an upscale dining option complete with stunning beach views, head to award-winning Sandbar Restaurant. The seafood dishes are truly mouthwatering and favourites include the mussels, shrimp and calamari. If you have other culinary tastes, the sandwiches and salads are great options. Pair it with a tasty drink as you watch the sun set over the water. And sweet lovers won't want to pass up the cheesecake or key lime pie; see menu.

  • Feeling Swell: For a more casual eating experience, check out Feeling Swell. You certainly will after sampling the cuisine here. With everything from unique appetizers like gator bites, conch fritters and crab cakes to quality entrees such as mahi mahi and grouper, you're sure to feel stuffed and satisfied. You can even dine outdoors on the patio, and there's often live entertainment, so it should prove to be quite an entertaining afternoon or evening; see menu.

Vacation Rentals in Anna Maria Island

Great Summer Rates! Steps Away from the Beautiful White Sandy Beach!

Located directly across the street from the white sandy beaches of the Gulf of Mexico, this large 2 bedroom, 2 bath, 2nd floor unit has been completely remodeled and tastefully decorated. This turn-key unit includes a fully equipped kitchen, brea...

Luxurious Two Bedroom Home with Heated Pool at North End of Island

This gorgeous 2 bedroom/2 bath home is located in an absolutely perfect location in the most desirable NORTH END area of Anna Maria. It has been completely and lovingly remodeled from top to bottom and is awaiting your visit. Surf’s Up is a shor...

The ultimate family vacation home

Brand new house with private heated pool, and fenced in yard. King bed in the master bedroom with it's own bathroom ,queen bed in the second bedroom,and two twin beds in the third room. Second bathroom located in the hallway between the other bed...

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