Unforgettable vacations await on Anna Maria Island

Blissful, beautiful, and boasting a feel of Old Florida, Anna Maria Island is a relaxed vacation destination on Florida’s picture-perfect Gulf Coast. The beaches are the big draw here, of course – the island’s broad stretches of powdery white sand lapped by aqua waters and dotted with historic wooden piers. Then comes everything else – from shopping to seafood to sunsets, there’s lots to look forward to in the island’s three resort cities of Anna Maria, Holmes Beach, and Bradenton Beach. Craft your own experience from the comfort of Anna Maria Island rentals. Whether you’re hanging out for the weekend or staying for the summer, they offer the perfect base for an unforgettable vacation.

Discover Anna Maria Island vacation home rentals

Anna Maria Island has a little something to tempt every traveler to its shores, so it makes sense that the island’s vacation rentals are equally diverse. From cozy cottages to sprawling oceanfront numbers with pools, there are countless places to stay on Anna Maria Island. Here’s a quick guide to popular rental styles and the best places to find them.

Anna Maria Island beachfront rentals

For those planning a vacation on Anna Maria Island, beachfront rentals are often a priority. And why not? There’s not much you won’t like about staying in homes that are steps away from the sandcastle building. Beach rentals pepper both sides of this seven-mile-long barrier island, although those in Holmes Beach are a favorite pick thanks to easy access to Manatee Public Beach. This spacious community beach offers all the amenities you could want, and then some – making rentals here an especially good choice for families.

Anna Maria Island rentals with pools

Anna Maria Island beaches are certainly gorgeous, but why stop there when it comes to relaxing on your vacation? Adding a pool to your rental wish list means you can enjoy the water whenever the mood strikes – whether that means an early morning dip before tucking into breakfast al fresco, splashing about with the kids before bed, or partying poolside after dark. Vacation house rentals with private pools offer the most freedom, but there’s plenty to be said for enjoying the savings that come from staying in Anna Maria Island condos with communal pools.

Anna Maria Island cottage rentals

Whether you’re looking for a beachfront pad or a rental with a pool, or a vacation home rental with both of those delights in place, you’ll find a string of Anna Maria Island cottage rentals that tick all the right boxes. And don’t think that cottage means tiny hideaway. There are some cute one-bedroom numbers, of course, though many of the cottage rentals on Anna Maria Island are ideal for large groups, with rentals often coming complete with four bedrooms, a medley of modern conveniences, and space enough for 10 guests or more.

Anna Maria Island vacations

So, now you know what to expect from the island’s choice of rentals, let’s peek at what you can expect from Anna Maria Island vacations. Coming up are top tips about the best time to visit, as well as the things to do when you get here and the ideal time to book your preferred rental.

Best time to visit Anna Maria Island

Temperatures on Anna Maria Island soar past 80 for much for the time between May and October, but the heat does bring with it a certain amount of humidity. The sticky Gulf heat can leave travelers wanting to enjoy the island when it’s just a bit cooler, and March is the most popular time to do exactly that. Budget travelers looking for cheap AMI vacation rentals should avoid the usual suspects: Labor Day, Easter, Thanksgiving, et al – concentrating their search instead on the affordable deals that pop up in October.

When to book Anna Maria Island rentals

With thousands of rentals peppered across the island’s three cities, finding a last-minute Anna Maria Island rental doesn’t usually end up being a problem. That said, if you want something specific like a pet-friendly pad with a pool, hot tub, and direct access to the beach, you’re probably better off getting bookings of that ilk nailed down in advance. It can also pay to be prepared if you’re vacationing in busy March or plan to celebrate one of the nation’s holidays on the island.

Things to do on Anna Maria Island

Once you’ve made it over the Sunshine Skyway and settled into your rental, it’s time to enjoy your stay. You might start with a jaunt to the resort city of Anna Maria where you’ll find Pine Avenue lined with cool shops, galleries, and restaurants. The wooden City Pier nearby has held court since 1911. Then there’s the Bridge Street Market in Bradenton Beach City; the perfect spot to pick something special to take home besides memories. Munching on grouper sandwiches as you browse is a must. End the day by catching the sunset from Bean Point Beach in the island’s north. It’s worth it.