LUXURY HOMES & APARTMENTS ON ANNA MARIA ISLAND

ANNA MARIA ISLAND HOLIDAYS

On the sun-kissed shores of the Gulf of Mexico, Anna Maria Island in Florida is a tropical paradise that promises a quintessential beach getaway. Known for its pristine white sandy beaches, crystal-clear turquoise waters, and charmingly laid-back vibe, this island gem is the perfect destination for a serene escape.

Our exclusive collection of holiday villas on Anna Maria Island offers an unparalleled blend of luxury and comfort, ensuring an unforgettable stay. Whether you’re seeking a romantic retreat, a family-friendly haven, or a grand coastal adventure, our villas provide the ideal home base.

Imagine waking up to the gentle sound of waves and enjoying breakfast with a view of the glistening ocean, then ending your day with a stunning sunset from your private terrace.

Check out our luxury villas and apartments on Anna Maria Island and head to the sunshine of Florida for an unforgettable villa vacation!

Why Visit Anna Maria Island?

  1. Anna Maria Island boasts some of the most beautiful beaches in Florida, featuring powdery white sand and clear, turquoise waters.

  2. Visitors can enjoy the unique local boutiques, cosy cafes, and waterfront dining. The island's friendly atmosphere and welcoming community make it an ideal spot for a peaceful and authentic getaway.

  3. From kayaking through mangrove tunnels to exploring scenic hiking and biking trails, Anna Maria Island offers a plethora of outdoor activities for nature enthusiasts and  is also a fantastic spot for wildlife viewing -  dolphins, manatees, and a variety of bird species.

Read the Anna Maria Island travel guide

Why stay with us?

Style and character are everything at Oliver’s Travels, and our collection of handpicked luxury rentals on Anna Maria Island have this in spades.
We have destination experts who know the ins and outs of all our regions, picking homes and apartments on Anna Maria Island that aren’t only unique, but also in the best locations.

Our helpful concierge team are on-hand to make your stay extra special. Whether you are looking for tips on local restaurants, advice on which key attractions to visit or any other extra service – consider them your holiday genie, who will happily grant your wishes.

Read more Read Less

Luxury Homes on Anna Maria Island: Our Top Picks

Villas with pools

Like it? Add to favourites to compare and share
Like it? Add to favourites to compare and share
Like it? Add to favourites to compare and share

Villas near the beach

Like it? Add to favourites to compare and share
Like it? Add to favourites to compare and share
Like it? Add to favourites to compare and share
View All (0)
View Large & Filter

Anna Maria Island Travel Guide

When to Visit Anna Maria Island

The best time to visit Anna Maria Island is from March to May and September to November. During these periods, the weather is pleasant, and the crowds are thinner compared to the peak summer season.

In March, visitors can enjoy the Anna Maria Island Art League's Springfest, showcasing local artists and craftsmen. The Food and Wine on Pine Festival in May offers a delightful experience with local cuisine, wines, and music. November brings Bayfest, a lively street festival with classic cars, live music, and local vendors.

The winter months, especially December through February, offer a mild climate ideal for those escaping colder regions, along with events like the Anna Maria Island Christmas Parade and the Privateers' Christmas Festival.

Summer - June to August - is hot and humid, but still popular due to school vacations, offering activities such as the Fourth of July Parade and fireworks.

Food and Drink on Anna Maria Island

Anna Maria Island's food and drink scene offers a delightful mix of coastal charm and diverse culinary options. Waterfront dining at the Sandbar Restaurant and Beach Bistro pairs stunning ocean views with fresh seafood and gourmet dishes. Casual spots like Rod & Reel Pier and Ginny's & Jane E's Café provide relaxed atmospheres with local favourites such as fish and chips and hearty breakfasts.

For drinks, craft breweries like Motorworks Brewing and beach bars like The Daiquiri Deck offer a variety of local brews and tropical cocktails. Speciality food shops, including Starfish Company for fresh seafood and Joe's Eats and Sweets for homemade ice cream, round out the island's vibrant culinary scene.

Another big draw to Anna Maria Island are the many independent, family-run restaurants right on the beachside, where you can step straight from the sidewalk on to the beach and dine with your toes in the sand. Bliss!


Fishing boats in Cortez Harbour

Things to do on Anna Maria Island

Anna Maria Island offers a variety of activities to suit all interests. Enjoy the pristine beaches like Bean Point and Coquina Beach, perfect for sunbathing, swimming, and shelling. Explore the island by bike or kayak, available for rent at several local shops.

Visit the historic Anna Maria City Pier for fishing and stunning views. Stroll along Bridge Street in Bradenton Beach for unique shops, dining, and the Bridge Street Market. Don’t miss the Anna Maria Island Historical Museum to learn about the island’s rich past.

For nature lovers, the Coquina Baywalk and Leffis Key Preserve offer scenic trails through lush landscapes. Anna Maria benefits from its west-facing position, meaning you can end your days with spectacular sunsets at one of the many beachside restaurants.

Why it's perfect for families

  • Great for babies: Anna Maria Island's calm, shallow waters and soft sandy beaches provide a safe and soothing environment for little ones to splash and play. What's more, the quartz-like structure of the sand means that it is always cool for little toes to take their first sandy steps.
  • Great for kids: With activities like building sandcastles, hunting for shells, and enjoying ice cream on the pier, Anna Maria Island offers endless fun and family-friendly attractions.
  • Great for teens: Teens can explore the island's water sports, like kayaking and paddleboarding, or hang out at lively spots on Bridge Street for snacks, shopping, and beach volleyball.

The island is just 7 miles long and 1 mile wide, and with road speed limits of just 20mph, you can be confident letting your young ones roam free. This makes it an ideal destination for youthful adventure and relaxation alike.

Top tips

  • Take a Segway or Electric Bike Tour: Discover the island in a unique way by taking a Segway or electric bike tour. These tours offer a fun and eco-friendly way to explore the island's hidden gems, including lesser-known beaches, historic sites, and scenic views. Companies like Zegway by the Bay provide guided tours that can give you insider knowledge about the island's history and local secrets while you effortlessly glide along.
  • Go on a Ghost Tour: Experience a different side of Anna Maria Island by joining a ghost tour. While the island is known for its sunny beaches, it also has a rich history that includes some spooky stories. The Haunted Anna Maria Island Ghost Tour takes you through the island's most haunted locations, sharing eerie tales and paranormal history. It's an unusual way to learn about the island's past and add a bit of thrill to your visit.

What Oliver Loves

The best thing about Anna Maria Island is its unspoiled, vintage Florida charm. Unlike many other tourist destinations in Florida, Anna Maria Island has successfully preserved its natural beauty and laid-back atmosphere.

Best Beaches on Anna Maria Island

Anna Maria Island is home to several stunning beaches that offer a variety of experiences for visitors. Bradenton Beach, located near the historic Bridge Street, features a lively atmosphere with beachfront bars, restaurants, and plenty of water sports activities. Holmes Beach, stretching along the central part of the island, is known for its powdery white sand and clear waters, perfect for sunbathing and swimming. For those looking for a quieter experience, the beaches near Bayfront Park provide a tranquil setting with scenic views of Tampa Bay and the Anna Maria City Pier, ideal for fishing and relaxing walks along the shore. You won’t be left wanting for sandy stretches!

Oliver’s Hidden Gem

Robinson Preserve is a 600-acre wetland habitat s with extensive walking, running, and biking trails located just a short drive off the island in nearby Bradenton. It offers a tranquil escape that many visitors might overlook.

Bean Point Beach

Bean Point Beach is known for its serene and secluded atmosphere, located at the northern tip of Anna Maria Island. This beach offers stunning views of the Gulf of Mexico and Tampa Bay, with pristine white sand and clear waters. It's an ideal spot for those seeking a peaceful retreat, with ample opportunities for shelling, birdwatching, and enjoying spectacular sunsets.

Coquina Beach

Coquina Beach, situated at the southern end of the island, is a favourite among locals and visitors alike. It features a wide stretch of soft sand, picnic areas, playgrounds, and amenities like restrooms and showers. The calm, shallow waters are perfect for swimming and snorkelling, while the nearby Coquina Baywalk offers scenic trails through mangrove-lined paths.

Manatee Public Beach

Manatee Public Beach is a bustling, family-friendly destination located in Holmes Beach. This beach provides plenty of amenities, including lifeguards, picnic tables, volleyball courts, and a beachfront café. The gentle waves and well-maintained facilities make it an excellent choice for families with children, and the ample parking and easy accessibility add to its convenience.

Getting There & Around

Anna Maria Island is served by Sarasota-Bradenton International Airport (SRQ), which is less than 30-minutes drive away. Just 60 miles up the coast, there is also Tampa International Airport (TPA).

To get there from the UK, either fly to Sarasota-Bradenton with a connecting flight in Atlanta, or fly direct to Tampa. British Airways offers direct flights, while other airlines like American Airlines, Delta Airlines, and United Airlines offer flights with one stop.

Once you land, you'll be at the beach in no time at all!

By Car

From the mainland, you can access Anna Maria Island via three main bridges: the Anna Maria Island Bridge (Manatee Avenue), the Cortez Bridge (Cortez Road), and the Longboat Key Bridge (Gulf Drive/State Road 789). Parking can be limited, especially during peak tourist season, but there are public parking areas at popular beaches and attractions.

By Public Transport

The Manatee County Area Transit (MCAT) offers a free trolley service on Anna Maria Island. The trolley runs daily from 6 a.m. to 10 p.m., covering the entire island from Coquina Beach at the south end to the City Pier at the north end. Trolleys run approximately every 20 minutes and have numerous stops along Gulf Drive, making it easy to hop on and off.

Top tips:

The free Anna Maria Island Trolley is a convenient and cost-effective way to get around the island. The trolley stops at popular spots like beaches, shops, and restaurants, making it easy to explore the island without a car. Download a trolley schedule or use a local app to track real-time trolley locations and minimize waiting times.

By Boat

Anna Maria Island has several marinas where you can dock your boat, such as the Bradenton Beach Marina and Galati Marina. These marinas offer services like fuel, supplies, and overnight docking.
Renting a boat or booking a boat tour can be a great way to explore the island’s coastline, nearby islands, and local waterways.

By Bicycle

Anna Maria Island is bike-friendly, with bike rental shops offering a variety of bicycles for all ages. The island has bike lanes and paths that run parallel to the main roads, making it easy and safe to explore by bike.

Biking is a great way to see the island at a leisurely pace and access areas that are not easily reached by car.

By Walking

The island’s small size and flat terrain make it very walkable. Many attractions, shops, and restaurants are within walking distance from each other, especially in the main towns of Anna Maria, Holmes Beach, and Bradenton Beach.

The Anna Maria Island Historical Society offers walking tours that highlight the island’s history and points of interest.