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Anna Maria Island vacation rentals

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Top-rated vacation rentals in Anna Maria Island

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Townhouse in Holmes Beach
Spectacular home 700 feet from the beach!
Beautiful home less than 2 blocks from the beach! Well-appointed 3 bedroom home with modern decor in quiet beach community. Smart TV, WiFi and free access to Netflix, washer/dryer, full kitchen with cooking essentials. Large screened in lanai. We supply everything for your dream beach vacation including bikes, beach towels, chairs, umbrellas, toys and games! Ping pong table and pool table in garage! Perfect house for families. Saturday to Saturday rental only during peak season (Jan-Aug).
$268 per night
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Rental unit in Holmes Beach
AMI Ohana Beach Resort A with fabulous salt pool!
The location is perfectly situated in the middle of the island with quick access to the beach (3 minute walk from door to shore without crossing Gulf Drive), Publix grocery store, Walgreens, Manatee Public Beach, shopping, restaurants and more. The free trolley stop is steps away offering an affordable way to explore the whole island. Ohana Beach Retreat is a newly renovated triplex in Holmes Beach on Anna Maria Island. Come enjoy our heated salt water pool in an oasis of palm trees.
$250 per night
Bungalow in Anna Maria
Bay Breeze Cottages #1 (The Mahi-Mahi)
Bay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the endless sun all year long, take a swim in our private heated pool with your favorite beverage, or head out anywhere on the island in our street legal gas powered golf carts to any of the local restaurants, piers, sand white sand beaches, and all other attractions the island has to offer. Come enjoy your own slice of paradise at Bay Breeze Cottages on Anna Maria Island.
$353 per night
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Anna Maria Island house rentals

Home in Holmes Beach
Breezy Harbor AMI pool retreat near the Beach
$444 per night
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Home in Holmes Beach
The Peachy Beach House, steps to the gulf
$414 per night
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Home in Bradenton Beach
Walk to Beach, free golf cart, and heated pool!
$300 per night
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Home in Anna Maria
Whispering Winds by Beach Boutique Rentals
$380 per night
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Home in Anna Maria
Dog-friendly beach bungalow with WiFi, private heated pool, balcony, and lanai
$436 per night
Home in Bradenton Beach
Ohana Beachside 2 Br Gulf view - 150 ft from Beach
$246 per night
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Home in Holmes Beach
Waterfront home with private dock
$234 per night
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Home in Bradenton Beach
Ohana Beachside 2 BR Bungalow - 150 ft from beach
$238 per night
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Home in Holmes Beach
Anna Maria - 3 Bd 2 Bth Home -Pool -Walk to Beach
$370 per night
Home in Anna Maria
Private Home with Heated Pool, Less than 1 Block
$235 per night
Home in Anna Maria
Renovated Home 1 Block to Beach
$275 per night
Home in Holmes Beach
Seaside Sunset- Waterfront home with boat dock
$231 per night
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Anna Maria Island villa rentals

Villa in Holmes Beach
Calico AMI - Tropical Heated Pool - Steps to Beach
$331 per night
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Villa in Anna Maria
Beachfront Home with Amazing Deck Views!
$294 per night
Villa in Holmes Beach
Comfortable island villa with private heated pool, courtyard & easy beach access
$237 per night
Villa in Holmes Beach
Island villa with heated private pool, tranquil courtyard, easy beach access
$234 per night
Villa in Anna Maria
Beachfront Home with Amazing Deck Views!
$379 per night
Villa in Holmes Beach
Amazing Villa at Islands West Resort! Close to
$112 per night
Villa in Holmes Beach
Vacay in luxury! So close to the beach!
$90 per night
Villa in Holmes Beach
Adorable villa near the beach!
$110 per night
Villa in Holmes Beach
Two story villa w/ balcony, screened lanai, & shared pool - close to the beach
$219 per night
Villa in HOLMES BEACH
Manatee Beach 1BR at Casa Coconut AMI#3
$219 per night
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Villa in Holmes Beach
Comfortable and near the beach! Pool access!
$71 per night
Villa in Holmes Beach
Beach Walk 1 Beach Side Villa
$215 per night

Anna Maria Island condo rentals

Condo in Bradenton Beach
★Right on the beach ★ Relax and Enjoy ♥ Sunsets!
$259 per night
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Condo in Holmes Beach
LOCATION! Cabana just steps from the beach!
$221 per night
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Condo in Holmes Beach
Steps to the beach! Updated Condo at The Terrace
$216 per night
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Condo in Bradenton Beach
Luxury, Fully Stocked, Next to Pool & Beach-202
$211 per night
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Condo in Holmes Beach
Beachfront Bungalow! Newly updated 1 bedroom!
$329 per night
Condo in Holmes Beach
Island Beach Paradise, Close to Everything, Bikes
$205 per night
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Condo in Bradenton Beach
Beach Escape & Pool, steps to Gulf & restaurants
$225 per night
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Condo in Holmes Beach
Sea Breeze ~ The Perfect Getaway
$179 per night
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Condo in Holmes Beach
Right on the Sand! Incredible Views!
$267 per night
Condo in Holmes Beach
Cute 1/1 heated pool/jacuzzi 5 min Walk to beach
$388 per night
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Condo in Bradenton Beach
Charming, newly renovated 2BR/2Bath condo on beach
$225 per night
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Condo in Bradenton Beach
If this isn't your view, you need to change your
$338 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.


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.