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Anna Maria Island vacation rentals

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Top-rated vacation rentals in Anna Maria Island

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  1. Entire home
  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.

G$30,584 per night
  1. Entire rental unit
  2. Holmes Beach
Villa Shrimp - Cute Studio Villa at Islands West Resort! Vacay in luxury so close to the beach!

Resort Unit Layout: • Studio unit - King bed, bathroom, efficiency kitchen and dining table for 2 Islands West Resort Features: • Shared Pool • Shared BBQ grills and Outdoor "Living Room" with cozy couches and lounge chairs to enjoy the beautifully lush landscaping • Brand-new Luxury Villas • Just a 2-minute walk to the beach! • Unbeatable central location close to grocery store and shops • Pet Friendly Welcome to Villa Shrimp! If you have ever wanted to experience the "Tiny House Living" trend, then you are in luck! Make yourself at home at this brand new construction bungalow! This top-notch villa is beautifully decorated and has all the conveniences you could want. Inside you will find a cozy studio living space that consists of a king-sized bed, kitchenette and a cute dining area that seats two. Curl up after a long day of frolicking at the beach and watch your favorite show on the large flat-screen TV, or maybe take a well-deserved nap! If you are the type of person who doesn't want to miss a beat, then walk out your back door and have a seat in your lushly landscaped, private patio space. Or, perhaps meander down the pathways of the shared courtyard to the outdoor "living room" featuring comfy couches and loungers to get some sunshine. Meet some new friends up on the sundeck or take a dip in the heated community pool that all of the Islands West villas share! Everything you could want is in close proximity to this awesome little house. You are across the street from the beach and just a couple blocks away from shops! Come check out this property at the luxury Islands West Resort on Anna Maria Island today and have the time of your life! This property allows pets - there will be an additional pet fee associated. AMI Locals Pet Policy: Dogs are allowed under certain conditions and ALL animals, including service animals, must be disclosed and approved prior to arrival. We cannot accept cats. There will be an additional pet fee charged upon approval by AMI Locals. Weight limit of 50 lbs max total for 1 or 2 dogs combined. No dangerous breeds allowed. Please see our AMI Locals Rental Policies for full details. 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.

G$25,741 per night
  1. Entire rental unit
  2. Holmes Beach
Villa Sand Dollar - New, fun and close to the beach, 1 bedroom Villa at the Islands West Resort!

Resort Unit Layout: • Bedroom 1 - King bed, full bathroom in the hallway with shower/tub combo There is also a Queen Sleeper Sofa in the Living Room Islands West Resort Features: • Shared Pool • Shared BBQ grills and Outdoor "Living Room" with cozy couches and lounge chairs to enjoy the beautifully lush landscaping • Brand-new Luxury Villas • Just a 2-minute walk to the beach! • Unbeatable central location close to the grocery store and shops • Pet Friendly Welcome to Villa Sand Dollar at The Islands West Resort! If you have ever wanted to experience the "Tiny House Living" trend, then you are in luck! Make yourself at home at this brand new construction bungalow! This top-notch villa is beautifully decorated and has all the conveniences you could want. Inside you will find a cozy main living space that consists of a kitchen with full-size appliances, a dining area that seats four, and a comfortable sleeper sofa. Curl up after a long day of frolicking at the beach and watch your favorite show on the large flat-screen TV. Or maybe take a well-deserved nap in the bedroom on the super plush, pillow-topped king size bed! If you are the type of person who doesn't want to miss a beat, then walk out your back door and have a seat in your lushly landscaped, private patio space. Or, perhaps meander down the pathways of the shared courtyard to the outdoor "living room" featuring comfy couches and loungers to get some sunshine. Meet some new friends up on the sundeck or take a dip in the heated community pool that all of the Islands West villas share! Everything you could want is in close proximity to this awesome little house. You are across the street from the beach and just a couple blocks away from shops! Come check out this property at the luxury Islands West Resort on Anna Maria Island today and have the time of your life! This property allows pets - there will be an additional pet fee associated. AMI Locals Pet Policy: Dogs are allowed under certain conditions and ALL animals, including service animals, must be disclosed and approved prior to arrival. We cannot accept cats. There will be an additional pet fee charged upon approval by AMI Locals. Weight limit of 50 lbs max total for 1 or 2 dogs combined. No dangerous breeds allowed. Please see our AMI Locals Rental Policies for full details. 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.

G$30,136 per night

Vacation rentals for every style

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Anna Maria Island house rentals

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  2. Anna Maria
2nd House from the Beach with No Roads to Cross
G$51,183 per night
SUPERHOST
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  2. Anna Maria
Memories are Made in Flip Flops
G$54,055 per night
SUPERHOST
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  2. Anna Maria
Anna Cabana B
G$35,996 per night
SUPERHOST
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  2. Holmes Beach
Sandy Toes Luxury Villa - 300 steps to the beach
G$42,304 per night
SUPERHOST
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  2. Anna Maria
SunKissed Cottage
G$159,973 per night
SUPERHOST
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  2. Bradenton Beach
5 STARS! Tropical Salt H2O Pool, Steps to BEACH!!
G$79,317 per night
SUPERHOST
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  2. Holmes Beach
AMI Sand Dollar
G$41,688 per night
SUPERHOST
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  2. Holmes Beach
The Peachy Beach House, steps to the gulf
G$59,854 per night
SUPERHOST
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  2. Bradenton Beach
Ohana Beachside Studio - 150 ft from the beach
G$34,830 per night
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  2. Bradenton
Chiclana II at Sunny Shores 1.2 miles to Beach
G$15,248 per night
SUPERHOST
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  2. Holmes Beach
Salty Harbor AMI pool retreat 6min to the Beach🏝
G$64,872 per night
SUPERHOST
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  2. Holmes Beach
Waterfront home with private dock
G$33,485 per night

Anna Maria Island villa rentals

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  2. Holmes Beach
CALICO★Tropical Pool★Walk to Beach★Family Friendly
G$106,253 per night
SUPERHOST
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  2. HOLMES BEACH
Casa Coconut AMI#1 @Manatee Beach
G$33,485 per night
SUPERHOST
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  2. HOLMES BEACH
Manatee Beach 1BR at Casa Coconut AMI#3
G$26,578 per night
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  2. Longboat Key
Gulf to Bay Resort - 1 BR
G$24,276 per night
  1. Entire villa
  2. Holmes Beach
Island villa with heated private pool, tranquil courtyard, easy beach access
G$46,041 per night
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  2. Holmes Beach
Comfortable island villa with private heated pool, courtyard & easy beach access
G$46,669 per night
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  2. Holmes Beach
PALM HAVEN BEACH SIDE VILLA
G$46,640 per night
  1. Entire villa
  2. Holmes Beach
Newly-built home near Gulf beaches with heated private pool & free WiFi
G$70,527 per night
  1. Entire villa
  2. Anna Maria
Northshore Beach House - North Anna Maria Island
G$46,251 per night
  1. Entire villa
  2. Holmes Beach
BEACH WALK #1 BEACH SIDE VILLA
G$42,094 per night
  1. Entire villa
  2. Holmes Beach
Chic on the Beach Side B
G$68,016 per night
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  2. Holmes Beach
Upscale tropical getaway with private pool & spa, elevator, and more
G$77,224 per night

Anna Maria Island condo rentals

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  2. Holmes Beach
Anna Maria by the Bay (minimum rental is 30 days)
G$24,067 per night
SUPERHOST
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  2. Holmes Beach
Beach Escape - Make Memories on Anna Maria Island!
G$35,996 per night
SUPERHOST
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  2. Holmes Beach
Beach, Pool, Tennis, Bikes, Close to Everything
G$29,299 per night
SUPERHOST
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  2. Holmes Beach
Ocean View Oasis
G$20,091 per night
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  2. Bradenton Beach
AMI Beach + Gulf View Retreat
G$51,213 per night
SUPERHOST
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  2. Bradenton Beach
★Right on the beach ★ Relax and Enjoy ♥ Sunsets!
G$50,466 per night
  1. Entire condo
  2. Holmes Beach
Coconuts Beachfront #110, amazing just-updated 1 bedroom beachfront condo!
G$49,181 per night
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  2. Bradenton Beach
Anna Maria Island Beach Waves
G$30,764 per night
SUPERHOST
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  2. Holmes Beach
Island Beach Paradise, Close to Everything, Bikes
G$35,757 per night
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  2. Bradenton Beach
Anthony Beach Cottages - Gulf View Condo
G$57,552 per night
SUPERHOST
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  2. Bradenton Beach
Beachfront condo in paradise
G$46,041 per night
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  2. Bradenton Beach
Amazing View, Updated Beachfront Condo
G$45,832 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.