Vacation Rentals in Anna Maria Island

Anna Maria Island is crammed with beautiful vacation properties, including plenty of elegant 19th and early 20th century single-storey villas. These vacation rental properties are almost always within walking distance of the shore, have spacious yards, pools and room for a whole family to stretch out in their living areas.

Another feature of the island is its assortment of vacation apartments. All along Gulf Drive, from Bradenton Beach to Anna Maria, you’ll find apartment blocks and rental home options that have been divided into large holiday apartments. If you need an affordable, conveniently located spot, they could be ideal.

Anna Maria Island, FL is a barrier island located just off the west coast of Florida, just north of Sarasota and across Tampa Bay from St Petersburg. The island stretches for seven miles in total, and the coast is lined with soft, sandy beaches along the whole length.

Never more than two miles across, the whole island is served by handy trolley buses, and traveling between beaches is simple. Getting to Anna Maria Island, FL is almost as easy. Tampa Airport is just a few miles to the southeast, and has connections to all major US cities. There are regular shuttle buses from the airport to Anna Maria Island, as well as car rental services if you need your own vehicle.

While you can rent a car or 4x4 during your stay, it’s more fun to rent a sailing or powerboat during your stay. There are marinas with boat hire companies at Bradenton Bay and Bimini Bay, and you can hop between quays in your rental craft, seeing every inch of the island’s coast.

Anna Maria Island, FL is a superb place to test your fishing skills. Join a skipper at the port or rent your own boat and fish for Gulf species like mackerel, red snapper or redfish until the sun goes down.

Both the east and west coasts of Anna Maria Island offer superb beaches, including Bradenton, Manatee, Holmes, Coquina and Cortez Beach. Sunbathe, snorkel in the emerald waters, play some volleyball and enjoy the endless sunshine.

Anna Maria Island has its cultural side, too. The Bradenton Blues Festival attracts huge names in December, while the waterfront in Anna Maria becomes a thriving arts venue when the Ringling International Arts Festival comes to town in October.

Public beaches like Coquina and Manatee have large parking lots, beautifully soft, warm sand, beautiful green waters, and enough space to enjoy whatever beach activities you desire.

It’s not all about beaches on Anna Maria Island. You can also hire kayaks and paddle to Leffis Key and the mangrove tunnels in Robinson Preserve. Both are magical natural locations, and are full of birdlife, turtles and marine life.

Shopping is a major activity on Anna Maria Island, and each beach seems to have its own market. One of the best places to head for craft bargains is Bradenton Beach’s Bridge Street Market (open on Saturdays), and you can shop for fine art at Bradenton’s Village of the Arts as well.

When you visit the Gulf, seafood is almost always high on the agenda, and Anna Maria Island doesn’t disappoint. Gastronomic highlights include Sandbar, the Beach Bistro and Sign of the Mermaid, but there’s no shortage of great spots.

As the sun sets over the Gulf of Mexico, the view is incredible. Find a spot on the west coast of the island, grab a cocktail and enjoy the show. In summer, you may even have the chance to see turtle hatchlings make their way to the sea – another extraordinary spectacle.

Anna Maria Island has a sub-tropical climate, with temperatures averaging 75 degrees all year-round. They rarely dip far below that point, although sea temperatures rise considerably during the summer. Rainfall is moderate, but slightly higher in the summer (although it tends to be limited to afternoon showers).

Driving around the island is simple, with Gulf Drive running along its whole length. However, it makes sense to become acquainted with the trolley, which runs from early morning to 22:30 and stops every four blocks along a north-south route.

Festivals are a big deal on the island. There are annual blues and arts events in Bradenton, as well as the Bayfest event in October, which has a classic rock theme. Cortez hosts an annual seafood festival, while January brings the Manatee County Fair. There’s always something going on.

How much do you pay, on average, for vacation rentals in Anna Maria Island?

We can see from our data that Anna Maria Island has an average price of $405.91 per night, a relatively high one under the destinations in the USA.

During which months can you find the best price for vacation rentals in Anna Maria Island?

After analyzing our data from last year, the months at the lowest possible cost in Anna Maria Island are October, November and May, with average prices of $307.03, $344.98, and $352.9, respectively.

When does the price of vacation rentals in Anna Maria Island go up the most?

Following the data observed in 2020, costs per night for accommodation here are usually higher, on average, during the months of February ($568.6), March ($559.38), and April ($468.58).

Should I plan a trip to Anna Maria Island well in advance?

You should book your stay well in advance when visiting Anna Maria Island, as only 17% of our accommodations are usually available throughout the year.

What time of the year can I find more free vacation rentals?

The months when it's the easiest to find free accommodation in Anna Maria Island are September (the average amount of properties that are free reached 31.25% of the total in 2020), December (29%), and April (25.25%).

Which months is it more difficult to find available vacation rentals?

The month with the highest average booked rental figures is February (only 1.2% of properties were available on average in 2020). Followed by March (5.75%), and June (7.25%).

Are there many rentals in Anna Maria Island?

We have 2900 properties for you in Anna Maria Island, provided by our 6 local and international partners.