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Anna Maria Island house rentals

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Top-rated house rentals in Anna Maria Island

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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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SunKissed Cottage

Beachfront, North End, large 2 bedroom with expansive views of the dolphins frolicking in the azure waters of the North End of Anna Maria Island. BBQ grill, bikes, paddle boards, kayak and a golf cart all included. Your backyard is a beautiful view of Egmont Key & the Skyway Bridge and your front yard is a lushly landscaped private, heated pool. Walk to the Rod & Reel Pier where dolphins frolic every afternoon or walk to Pine Avenue for some local shopping.

$764 per night
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  2. Holmes Beach
The Peachy Beach House, steps to the gulf

Just opened up for June ‘22. Please note- PRICE IS GREATLY DECREASED BECAUSE POOL CONSTRUCTION happening. Heavy construction is complete Steps from semi-private gulf beach, this 3 story on a quiet street in north Holmes Beach has all you need for a wonderful beach vacation. Well-stocked kitchen, 2 TVs, large master which is more like resort suite with new (May 2021) tempurpedic king bed with gulf views. You’ll find: crib, high chair, beach chairs, wagon, umbrella, beach toys and towels!

$220 per night

Vacation rentals for every style

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Anna Maria Island vacation rentals

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  2. Holmes Beach
Villa Shrimp - Cute Studio Villa at Islands West Resort! Vacay in luxury so close to the beach!
$123 per night
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Villa Sand Dollar - New, fun and close to the beach, 1 bedroom Villa at the Islands West Resort!
$144 per night
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Turtle Cottage - Anna Maria Island
$265 per night
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Bradenton Beach Sunsets II
$186 per night
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Little Dream by Anna Maria Island Accommodations
$80 per night
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Bay Breeze Cottages #2
$292 per night
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Low Tide by AMI Locals
$411 per night
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Soakin up Sun by AMI Locals
$69 per night
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Beachfront Bungalow! Newly updated 1 bedroom!
$276 per night
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PLAYA ESMERALDA INN suite #1A
$181 per night
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Lovely 1 bedroom apartment with partial water view
$185 per night
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Villa Seashell - Amazing 1 bedroom Villa at new Islands West Resort! Close to beach with pool!
$101 per night

Anna Maria Island villa rentals

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CALICO★Tropical Pool★Walk to Beach★Family Friendly
$500 per night
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Casa Coconut AMI#1 @Manatee Beach
$161 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
$140 per night
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Newly-built home near Gulf beaches with heated private pool & free WiFi
$330 per night
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Island villa with heated private pool, tranquil courtyard, easy beach access
$219 per night
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Upscale tropical getaway with private pool & spa, elevator, and more
$369 per night
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Chic on the Beach Side B
$325 per night
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PALM HAVEN BEACH SIDE VILLA
$226 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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Northshore Beach House - North Anna Maria Island
$221 per night
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BEACH WALK #1 BEACH SIDE VILLA
$205 per night

Anna Maria Island condo rentals

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Ocean View Oasis
$96 per night
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Coconuts Beachfront #110, amazing just-updated 1 bedroom beachfront condo!
$235 per night
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★Right on the beach ★ Relax and Enjoy ♥ Sunsets!
$239 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 Island Beach Waves
$147 per night
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Amazing View, Updated Beachfront Condo
$226 per night
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Beach, Pool, Tennis, Bikes, Close to Everything
$134 per night
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Anthony Beach Cottages - Gulf View Condo
$275 per night
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Beachfront condo in paradise
$226 per night
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Beach Haven #204
$200 per night
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Anna Maria Island Beach Condo w/ Stunning Views!
$235 per night
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Island Paradise #4 - Stunning Gulf Front Views
$208 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.