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Anna Maria Island vacation rentals

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Vacation rentals for every style

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Popular amenities for Anna Maria Island vacation rentals

Self check-in
Free parking on premises
Beachfront
Private bathroom
Gym

Anna Maria Island house rentals

Guest favorite

Home in Bradenton Beach

5 out of 5 average rating, 46 reviews

Beach front! Trolley/Sunsets/Pier/Restaurants!

Guest favorite

Home in Bradenton

4.96 out of 5 average rating, 211 reviews

Cozy Cottage R-Steps to Riverwalk/Close to Beaches

Guest favorite

Home in Holmes Beach

4.93 out of 5 average rating, 41 reviews

Backyard Bliss Anna Maria Island

Guest favorite

Home in Bradenton Beach

4.82 out of 5 average rating, 133 reviews

50 Steps to Beach Villa Hot Tub 1bd modern cottage

Guest favorite

Home in Anna Maria

4.98 out of 5 average rating, 44 reviews

Ready to Host! Anna Maria Chateau. Private Pool!

Guest favorite

Home in Holmes Beach

5 out of 5 average rating, 19 reviews

5 min walk to beach, private pool & spa, elevator

Guest favorite

Home in Holmes Beach

4.95 out of 5 average rating, 94 reviews

The Peachy Beach House, steps to the gulf

Guest favorite

Home in Indian Rocks Beach

4.98 out of 5 average rating, 119 reviews

Beachfront Bungalow w/ Pool & Hot Tub in IRB

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Anna Maria Island villa rentals

Guest favorite

Villa in Sarasota

4.96 out of 5 average rating, 164 reviews

Newly Renovated- 150 Yards to Beach & Restaurants!

Guest favorite

Villa in Safety Harbor

5 out of 5 average rating, 128 reviews

Villa Key West "Villas by Christine"

Guest favorite

Villa in Tampa

4.9 out of 5 average rating, 161 reviews

Villa Perdomo Family

Guest favorite

Villa in Largo

4.91 out of 5 average rating, 112 reviews

Poolside Palms Private Pool & Game Room - 7 Min to Indian Rocks Beach

Guest favorite

Villa in Siesta Key

4.91 out of 5 average rating, 152 reviews

Mermaid Villa Ocean Front!

Guest favorite

Villa in Holmes Beach

4.97 out of 5 average rating, 65 reviews

Calico - Family Oasis - Steps from the Sand

Guest favorite

Villa in Tampa

4.91 out of 5 average rating, 116 reviews

Boho -Minimalist villa

Guest favorite

Villa in HOLMES BEACH

4.95 out of 5 average rating, 38 reviews

Steps from the beach 2BR @Manatee Beach

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Anna Maria Island condo rentals

Guest favorite

Condo in Indian Shores

4.96 out of 5 average rating, 112 reviews

Serenity by the Sea * Steps to the Ocean*

Guest favorite

Condo in Bradenton Beach

4.83 out of 5 average rating, 232 reviews

A+ location! Steps to beach, walk to Bridge St! #1

Guest favorite

Condo in Siesta Key

4.96 out of 5 average rating, 296 reviews

WE ARE OPEN—On the Beach; Siesta Key SunBum Studio

Guest favorite

Condo in Siesta Key

4.94 out of 5 average rating, 190 reviews

Siesta key getaway!

Guest favorite

Condo in Longboat Key

4.91 out of 5 average rating, 160 reviews

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Guest favorite

Condo in Bradenton Beach

4.86 out of 5 average rating, 103 reviews

Oceanfront Condo for Beach Lovers

Guest favorite

Condo in Holmes Beach

4.85 out of 5 average rating, 143 reviews

Anna Maria Island-just a few steps to the beach

Guest favorite

Condo in Longboat Key

4.99 out of 5 average rating, 112 reviews

Silver Sands - Winter Availability!

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Your guide to Anna Maria Island

Introduction

With its beautiful beaches and brilliant blue waters, this seven-mile barrier island offers a nostalgic idyll on the Gulf of Mexico. Over the years, residents have proudly resisted development, so Anna Maria’s vibe is decidedly low-key, with thatched-roof open-air bars and fresh fish restaurants dotting the waterfront. Here, where the island-wide speed limit is 35 miles per hour, the pace of life is literally slower. There are three small towns on the island — Bradenton Beach in the south, Holmes Beach in the middle, and the largest, Anna Maria, in the north — each with its own charms.

The best time to stay in a vacation rental in Anna Maria Island

January through April and October through December are popular months to visit as they offer temperatures between 70 and 80 degrees Fahrenheit. April and May bring temperatures in the high 80s, and June through September can be quite hot, with temperatures in the 90s. If you opt to book one of the area’s vacation rentals for a winter holiday, make sure to pack a layer for cooler evenings.

Top things to do in Anna Maria Island

Coquina Beach

You won’t have trouble finding a spot for your towel on this serene beach with sand dunes and waving beach grass. Although more sedate than nearby Manatee Public Beach, which draws more crowds, Coquina Beach doesn’t scrimp on amenities. There are picnic tables, bathrooms, and a lifeguard, making it an ideal spot for families. Bring a picnic, or fuel up at the Coquina Beach Cafe, which serves breakfast, fish tacos, and — for the grown-ups — frozen drinks at its tiki bar.

Coquina Baywalk

Get acquainted with the island’s unique ecosystem on this short walk through Leffis Key Preserve on an elevated wooden walkway. You’ll see mangrove trees alongside thousands of native plant species. You’re also likely to spot local wildlife such as geckos, crabs, stingrays, and birds — including the remarkable frigatebird, famous for showboating males who inflate an enormous red pouch under their beaks when courting.

Bean Point Beach

If you’re yearning for that Robinson Crusoe feel, Bean Point Beach is your best bet. Located on the northern tip of the island, this gorgeous stretch of sand is where the island’s founding family, chose to build their estate in 1892. Their homestead is long gone, but the beauty that drew them to the land is very much present. Off the beaten path, this public beach has no parking lots or lifeguard. What it does have is scenic splendor, a calming sense of privacy, and unobstructed sunset views.

Frequently Asked Questions

  • How is the weather in Anna Maria Island?

    Anna Maria Island has a subtropical climate with warm, humid summers and mild winters. The average summer temperature is 90°F (32°C), while in winter it drops to around 70°F (21°C). Rain is frequent from June to September, but showers are usually short and followed by sunshine.

  • What are some of the best things to do in Anna Maria Island?

    Visitors to Anna Maria Island often enjoy activities like paddling through the mangroves on a kayak, taking a dolphin watching tour, or exploring the Anna Maria Island Historical Society. For beach lovers, the island's seven miles (11.2 km) of coastline provide plenty of opportunities for swimming and shell collecting.

  • What is the best time of year to visit Anna Maria Island?

    The most popular time to visit Anna Maria Island is from February to May, when the weather is mild and rainfall is rare. During this time, the island hosts events such as the Anna Maria Island Art League's Springfest, a fine arts and crafts festival, and the Food and Wine on Pine, a celebration of local cuisine and vineyards.

  • What are the best places to stay in Anna Maria Island?

    The island is divided into three cities: Anna Maria, Holmes Beach, and Bradenton Beach. Each has its unique charm. Anna Maria is known for its laid-back vibe and historic buildings, Holmes Beach for its shopping centers and restaurants, and Bradenton Beach for its beachfront accommodations and lively nightlife.

  • What are the best places to visit in Anna Maria Island?

    Popular places to visit on Anna Maria Island include the Bean Point Beach, with its serene atmosphere and stunning sunsets, the Anna Maria Island Historical Museum, and the Anna Maria City Pier. The island also has a thriving arts scene, making the Island Gallery West a frequented spot.

  • What are some hiking trails in Anna Maria Island?

    Coquina Baywalk at Leffis Key is a great hike option in Anna Maria Island. It's a 1.5-mile (2.4 km) trail that meanders through mangrove tunnels and overlooks Sarasota Bay. Another recommended trail is the Robinson Preserve, just a 10-minute drive off the island. It has over 7 miles (11.2 km) of multi-use trails and is known for its diverse wildlife.

  • What are some family activities to do in Anna Maria Island?

    Families on Anna Maria Island frequently spend time building sandcastles at Manatee Public Beach, exploring the interactive exhibits at the Anna Maria Island Historical Society, or having a picnic at Bayfront Park. Additionally, the Island Scooter Store provides bike rentals for family cycling excursions.

  • What are some of the best day trip ideas in Anna Maria Island?

    Day trips from Anna Maria Island often include a visit to the Mote Marine Laboratory & Aquarium in Sarasota, a 30-minute drive away, or exploring the vibrant city of St. Petersburg, just an hour's drive from the island. Closer to home, the De Soto National Memorial offers historical exhibits and nature trails.

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