The “Old Florida” Feeling On Anna Maria Island

There was a time not too long ago in Florida when life was quieter, evenings were peaceful, kids ran free, and people relaxed while they enjoyed the outdoors without a care in the world. If you’re looking for that old time Florida feel for your next vacation (without a time machine), you’ll find exactly that on Anna Maria Island. Booking an Anna Maria Island vacation rental on our website will give you the opportunity to travel to a place that will remind you of days past while providing every possible modern amenity.

Old Florida, Anna Maria Island

Visiting Anna Maria Island is like going back to a better time

Visiting Anna Maria Island is like taking a step back in time to Florida in the 40s and 50s. When staying on Anna Maria Island you’ll find a seven-mile stretch of exquisite white sand lining the Gulf of Mexico and waves moving gently with the ocean breeze. You might catch guests at The Sandbar enjoying a sunset wedding and guessing the exact minute of sunset to win a bottle of wine or a dessert. The crowd is subtle, however, and there are no panhandlers or wall-to-wall bars here. There are no fast food chains or hotels, and the high-rise condos are saved for other Florida vacation spots.

Homes and buildings are small allowing for beautiful views and a unique classic feel

In fact, on Anna Maria Island all the homes are small, lying low to the horizon. Nothing is taller than three stories, giving the island a classic 40s/50s neighborhood look and keeping the views wide open. Kids ride bikes or run down the sidewalks while parents relax poolside. The peace on this island is difficult to find elsewhere in Florida. Many people from around the world flock to this island to experience an America before it became speckled with brand names and tall buildings.

Wear your casual clothes to dinner on Anna Maria Island

People from all backgrounds come here to enjoy a laid-back, friendlier living experience. This doesn’t mean the island is expensive; the wide variety of Anna Maria Island vacation rentals provide affordability for nearly every vacation budget. Similarly, Anna Maria Island restaurants vary with their dress code, allowing vacationers to choose between jeans and t-shirt, or a fancy night out.

Be sure to stop by Ginny’s And Jane E’s

An old IGA grocery, which is an American timestamp from the 50s and 60s, is now Ginny’s and Jane E’s, where visitors meet for foamy lattes, delicious breakfast items and crafts from local artists. The owners appreciate a bit of whimsy, always smiling, and decorating their shop to reflect the light, low-key feel of the island. From this fairy-tale shop, visitors can take in beautiful views of the ocean.

Stop by the Dockside Bar or Bridgetender Inn for a few evening drinks

The nighttime brings relaxing drinks at the Dockside Bar or Bridgetender Inn, where waitresses call everyone pet names, such as “dear.” The friendliness of the service and the familiarity of the businesses on this island makes visitors feel at home, and reminiscent of old America, when we all knew our neighbors. The bars close at 10 when the whole island rolls up its sidewalks and requests that all visitors maintain a low profile.

The island has plenty of travelers, and getting around is easy. As a bonus, Anna Maria maintains the friendliness of yesterday. No one flaunts their riches, and everyone greets everyone else with an old-time neighborly love not found in other vacation spots. Even the animals move in a lackadaisical manner; herons cross the roads on the north end of the island undisturbed. They know they are safe, and they seem to absorb the calming presence of the island.

When you’re ready to book a relaxing Old Florida vacation and return to the days when everyone said hello, call Lizzie Lu’s Island Retreat at (941)-782-8152 or book your Anna Maria Island vacation rental right on our website!


  • 6000 Marina Drive
    Holmes Beach, FL 34217 USA