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Anna Maria Island vacation rentals

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Popular amenities for Anna Maria Island vacation rentals

Anna Maria Island house rentals

Guest favorite
Home in Bradenton Beach
Paradise! Steps2 Private Beach & Tropical Yard!
Dec 13 – 20
$449 per night
4.97 out of 5 average rating, 149 reviews
Guest favorite
Home in Bradenton
Peaceful Braden River Oasis: Cottage
Sep 29 – Oct 6
$87 per night
4.94 out of 5 average rating, 150 reviews
Guest favorite
Home in Bradenton
Cozy Cottage R-Steps to Riverwalk/Close to Beaches
Aug 8 – 15
$105 per night
4.96 out of 5 average rating, 193 reviews
Guest favorite
Home in Holmes Beach
Twin Palms: Big House Steps to Beach w/Lush Pool
Aug 25 – Sep 1
$391 per night
4.97 out of 5 average rating, 122 reviews
Guest favorite
Home in Holmes Beach
Captain's Quarters at Spinnakers Vacation Cottages
Dec 21 – 28
$395 per night
4.99 out of 5 average rating, 153 reviews
Guest favorite
Home in Bradenton Beach
Ohana Beachside 2 BR Bungalow - 150 ft from beach
Sep 4 – 11
$210 per night
4.89 out of 5 average rating, 236 reviews
Guest favorite
Home in Holmes Beach
Private Luxurious Ground Level Home
Sep 18 – 25
$350 per night
5.0 out of 5 average rating, 46 reviews
Guest favorite
Home in Anna Maria
Lamantin- 2 bed/2bath North End, beach 2 min walk
Aug 24 – 31
$336 per night
5.0 out of 5 average rating, 10 reviews

Anna Maria Island villa rentals

Guest favorite
Villa in Redington Shores
Beachside 1 min to sand W/D Priv patio Peaceful
May 14 – 21
$161 per night
4.9 out of 5 average rating, 119 reviews
Guest favorite
Villa in Sarasota
Newly Renovated- 150 Yards to Beach & Restaurants!
Jun 1 – 8
$275 per night
4.96 out of 5 average rating, 129 reviews
Guest favorite
Villa in Siesta Key
Mermaid Villa Ocean Front!
Jan 18 – 25
$682 per night
4.9 out of 5 average rating, 132 reviews
Guest favorite
Villa in Bradenton
Elegant private home 3Bdr/3bth
Jun 22 – 29
$225 per night
4.83 out of 5 average rating, 132 reviews
Guest favorite
Villa in Sarasota
Entire Standalone Villa,1.2k sf,1 block Lido Beach
Aug 14 – 21
$204 per night
4.9 out of 5 average rating, 180 reviews
Guest favorite
Villa in Safety Harbor
Villa Key West "Villas by Christine"
Jul 19 – 26
$165 per night
5.0 out of 5 average rating, 108 reviews
Guest favorite
Villa in Clearwater
V3- 1 BR, waterfront villa, 2 min walk 2 beach
May 16 – 23
$159 per night
4.91 out of 5 average rating, 210 reviews
Guest favorite
Villa in St. Petersburg
St. Pete Beach Oceanfront Villa Saltwater Pool
Feb 17 – 24
$285 per night
4.84 out of 5 average rating, 106 reviews

Anna Maria Island condo rentals

Guest favorite
Condo in Bradenton Beach
Beachfront condo in paradise
Jan 12 – 19
$326 per night
4.9 out of 5 average rating, 121 reviews
Guest favorite
Condo in Redington Beach
NoCleaningFees/AmazingBeachCondo/AwesomeAmenities2
Jun 28 – Jul 5
$116 per night
4.97 out of 5 average rating, 245 reviews
Guest favorite
Condo in Holmes Beach
Beautiful beachfront condo for perfect vacation
Jul 3 – 10
$310 per night
4.96 out of 5 average rating, 116 reviews
Guest favorite
Condo in Longboat Key
Beachfront Resort, Ocean View, Pool, Tennis, Gym
Aug 18 – 25
$268 per night
4.93 out of 5 average rating, 143 reviews
Guest favorite
Condo in St. Pete Beach
Sunset Beach Condo in Treasure Island
Oct 17 – 24
$105 per night
4.91 out of 5 average rating, 199 reviews
Guest favorite
Condo in Indian Rocks Beach
Waterfront Condo w/ Boat dock, 2 min walk to beach
Nov 26 – Dec 3
$101 per night
4.79 out of 5 average rating, 222 reviews
Guest favorite
Condo in Redington Beach
Royal Orleans and Redington Beach ( Studio 203 )
Oct 17 – 24
$81 per night
4.91 out of 5 average rating, 105 reviews
Guest favorite
Condo in Longboat Key
Cute Condo with a Stunning View!
Sep 9 – 16
$236 per night
4.97 out of 5 average rating, 146 reviews

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.

Destinations to explore