Anna Maria Island vacation rentals

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Top-rated vacation rentals in Anna Maria Island

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  2. Anna Maria
Cozy Beachhouse 800 steps to beach

This beautiful home is only 800 steps from one of the most beautiful beaches in Southwest Florida. Great getaway for couples. Amazing restaurants and entertainment very close. Free trolley, endless things to do: kayaking, sunbathing, and relaxing.

$146 per night
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  2. Holmes Beach
Little Dream by Anna Maria Island Accommodations

Little Dream 203 64th St, Unit B Holmes Beach, FL 34217 1.5 Blocks to the Beach Cute, clean, charming is this ground level one bedroom duplex that sits a very short 1.5 blocks to the beach. And all of Anna Maria Island is at your fingertips with the free Island Trolley! Hop on at the entrance to the beach access and explore the Island from north to south. This unit comes with the use of the heated pool located in the North Beach Village Subdivision only a quick few minute walk away. The entry to the house opens up into the living area with comfortable seating and a flat screen TV. To the left is the kitchen and dining area. To the right is the bath with stand-up shower while straight ahead is the King Bedroom. This little Anna Maria Island dream sleeps 4! Bedroom 1: King with TV on Floor 1 Living Room: Queen Sleeper Sofa **Includes access to North Beach Village community pool** Vacation Rental Certificate VRC16-000139 You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property.

$80 per night
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  2. Holmes Beach
Soakin up Sun by AMI Locals

Welcome to Soakin up Sun! Step into paradise at our recently refreshed, canal front 1 Bedroom, 1 Bath home that’s tucked away in a quiet neighborhood of Holmes Beach. Experience coastal living surrounded by tropical landscaping, an oversized balcony with stunning bay views, a spacious layout, and just minutes from the white sugary sands of the Gulf. Close by to coastal dining, shopping, and the island trolley stop where you can set off to explore the 7 mile island of Anna Maria without needing to drive your own car. This bungalow has that “Old Florida,” charm and is the perfect beach getaway destination. The main living space is located on the second floor with an open style layout and an abundance of natural sunlight with doors opening up to the balcony for enjoying the bay breezes throughout the home. The kitchen overlooks the great room with an island set with breakfast stools and a dining table that can easily seat 4. Relax in comfort with a cushy sofa that unfolds to a queen size bed accommodating extra guests in the spacious living area. Off from the kitchen is the Queen suite with an ensuite bathroom featuring a soaking tub and step in shower. Spend your peaceful mornings with a coffee in hand at your private dock with vista views of the bay, as the tranquil waters will start your day off right! Whether your escaping to the island to soak up Vitamin-Sea, searching for seashells along the breathtaking coastline, or looking to kayak along the bay, there is something fun for everyone! Discover the beauty of Anna Maria by bike, catch a sunset or two as they are legendary, and live the island dream. Our Soakin up Sun vacation home awaits you!! Home Layout: Bedroom #1- Queen Bed * Queen size Sofa Sleeper in Living Room **Washer and Dryer are shared with Unit A - located directly beside Unit B- please access from front of property. *Please note: 2 cars maximum are able to park at this home. Please pull in straight and park one car in front of the other. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. This home is managed by AMI Locals, an Anna Maria Island property management company. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please Remember: *The City of Anna Maria, Holmes Beach, and Bradenton Beach all have noise ordinance policies in place, and they are enforced by local law enforcement and code enforcement officers. The goal of this program is not to limit your fun or vacationing experience, instead it is designed to ensure a quality stay for every guest and resident on our island. Please be mindful of our neighbors during your stay. Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.*

$69 per night

Vacation rentals for every style

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Anna Maria Island house rentals

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Sandy Toes Luxury Villa - 300 steps to the beach
$202 per night
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  2. Bradenton Beach
5 STARS! Tropical Salt H2O Pool, Steps to BEACH!!
$379 per night
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AMI Sand Dollar
$213 per night
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Ohana Beachside Studio - 150 ft from the beach
$171 per night
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Memories are Made in Flip Flops
$314 per night
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SunKissed Cottage
$764 per night
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Anna Cabana B
$172 per night
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2nd House from the Beach with No Roads to Cross
$303 per night
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Walk 2 Beach + PRIVATE Pool with TIKI + Golf Cart
$376 per night
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Starfish House 1/2 block to beautiful island beach
$300 per night
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3br/2b in Anna Maria w/ Private Heated Pool Oasis
$382 per night
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Breezy canalfront home w/ heated pool & dock - 3 blocks to Bean Point Beach
$321 per night

Anna Maria Island villa rentals

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Two story villa w/ balcony, screened lanai, & shared pool - close to the beach
$211 per night
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Island villa with heated private pool, tranquil courtyard, easy beach access
$219 per night
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Welcoming condo close to the beach with heated private pool and free WiFi
$316 per night
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Comfortable island villa with private heated pool, courtyard & easy beach access
$222 per night
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Manatee Beach 1BR at Casa Coconut AMI#3
$127 per night
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Casa Coconut AMI#1 @Manatee Beach
$160 per night
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Upscale tropical getaway with private pool & spa, elevator, and more
$369 per night
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  2. Longboat Key
Gulf to Bay Resort - 1 BR
$116 per night
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CALICO★Tropical Pool★Walk to Beach★Family Friendly
$511 per night
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Northshore Beach House - North Anna Maria Island
$221 per night
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PALM HAVEN BEACH SIDE VILLA
$227 per night
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BEACH WALK #1 BEACH SIDE VILLA
$206 per night

Anna Maria Island condo rentals

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Ocean View Oasis
$96 per night
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Beach, Pool, Tennis, Bikes, Close to Everything
$140 per night
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Island Beach Paradise, Close to Everything, Bikes
$185 per night
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  2. Bradenton Beach
Anna Maria Island Beach Waves
$147 per night
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★Right on the beach ★ Relax and Enjoy ♥ Sunsets!
$247 per night
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Anna Maria Island Sunshine Kiss Villa
$131 per night
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  2. Bradenton Beach
Bright open-concept condo with pool - near beach, restaurants, & pier
$124 per night
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Beach Escape - Make Memories on Anna Maria Island!
$167 per night
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Beachfront Bungalow! Newly updated 1 bedroom!
$296 per night
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Updated bayside condo with heated pool - across the street from the beach
$190 per night
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Anna Maria by the Bay (minimum rental is 30 days)
$115 per night
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Anna Maria - steps from the beach
$149 per night

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.


How do I get around Anna Maria Island?

Sarasota-Bradenton International Airport (SRQ) is the closest airport at 20 miles away. You can take a taxi or rent a car to carry you over one of the two bridges that connect Anna Maria Island to the mainland. Once you settle in, you may not use a car much. The island is extremely walkable, and operates a free trolley between 6 a.m. and 10 p.m. with 14 stops, including at the beaches. Many visitors also choose to rent bikes or golf carts.


When is 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.


What are the 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.