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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.

Superhost
Apartment in Bradenton Beach
Ohana Beachside 1 Bedroom B - 150 feet from beach
Aloha and welcome to our island home. "Ohana" is Hawaiian for family and that is who you are when you stay with us. Our home is designed for the ideal couples get away. There is 1 bedroom and 1 bath. An open dining and living space make the home feel comfy and roomy. We have a 3rd floor deck guests utilize to watch the sun sink into the earth over the Gulf of Mexico or enjoy soaking up the sun. You are 150 feet across Gulf Drive from stepping into the pristine white sands and turquoise waters of
$151 per night
Superhost
Cottage in Bradenton Beach
Bradenton Beach Sunsets 2, Anna Maria Island, FL
Fully furnished water view beach cottage located on beautiful Anna Maria Island directly across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with the queen pull out couch. Beach chairs/umbrellas/Boogie boards/laundry room, etc. provided. Three blocks from historic Bridge Street with lively restaurants and bars. Free island trolley and across the bridge from Cortez fishing village. Free off-street parking.
$154 per night
Superhost
Apartment in Bradenton Beach
A Cozy Bungalow on the bay.
A comfortable efficiency with a queen size bed, a full kitchen, a private bath, a great location and a lovely view. We are a two minute walk to Cortez beach & ten minute walk to beautiful Coquina beach. We supply beach chairs, umbrellas, wagons, towels and coolers. Restaurants, shopping and nightlife are just a 2 minute walk away. The free trolley will take you all around the island where there are many more great restaurants and stores.
$149 per night

Anna Maria Island house rentals

Superhost
Home in Bradenton Beach
Paradise! Steps2 Private Beach & Tropical Yard!
$355 per night
Superhost
Home in Anna Maria
Private 30' Pool and Boat Dock. Rated best on AMI
$261 per night
Superhost
Home in Holmes Beach
Waterfront home with private dock
$275 per night
Superhost
Home in Holmes Beach
Anna Maria Island Duplex w/ private pool (side B)
$218 per night
Superhost
Home in Bradenton
Palm Retreat Gold: Luxury Edition of #1 Rental
$205 per night
Superhost
Home in Anna Maria
Charming house w/heated pool,steps to beach-Unit A
$288 per night
Superhost
Home in Anna Maria
Beach House w/Private Pool & Hot Tub by Bean Point
$318 per night
Superhost
Home in Holmes Beach
Breezy Harbor AMI pool retreat near the Beach
$188 per night
Superhost
Home in Holmes Beach
The Peachy Beach House, steps to the gulf
$274 per night
Superhost
Home in Anna Maria
Soulshine: Dog Friendly! Pool, Dock on Canal
$321 per night
Superhost
Home in Bradenton Beach
Waterfront home with heated pool walk to Beach!
$371 per night
Superhost
Home in Holmes Beach
Couple’s Seatreat
$191 per night

Anna Maria Island villa rentals

Superhost
Villa in Sarasota
Newly Renovated- 150 Yards to Beach & Restaurants!
$175 per night
Superhost
Villa in Siesta Key
Mermaid Villa Ocean Front!
$549 per night
Superhost
Villa in Sarasota
Entire Standalone Villa,1.2k sf,1 block Lido Beach
$210 per night
Superhost
Villa in Clearwater
V1-2 BR, direct waterfront, 2 min walk to beach
$159 per night
Superhost
Villa in Bradenton
Elegant private home 3Bdr/3bth
$164 per night
Superhost
Villa in Redington Shores
Beachside 45 second walk to wide beautiful beach
$102 per night
Superhost
Villa in Sarasota
Cozy, pet-friendly Home 3 miles to Siesta Key #1
$149 per night
Superhost
Villa in Safety Harbor
Villa Key West "Villas by Christine"
$138 per night
Superhost
Villa in Sarasota
Hansen- Gorgeous 3BR/2BA Villa near Siesta Key
$201 per night
Superhost
Villa in Holmes Beach
Calico - Family Oasis - Steps from the Sand
$361 per night
Superhost
Villa in HOLMES BEACH
Great location near Manatee Beach 1BR at Casa Coco
$180 per night
Superhost
Villa in Siesta Key
Siesta Key BEACH SIDE villa/Private beach/pool
$166 per night

Anna Maria Island condo rentals

Superhost
Condo in Bradenton Beach
Beachfront condo in paradise
$282 per night
Superhost
Condo in Longboat Key
Oceanfront Getaway - Open Christmas Eve and Day!
$208 per night
Superhost
Condo in Holmes Beach
Anna Maria Beach Place...footsteps to the sands
$150 per night
Superhost
Condo in Siesta Key
On the Beach; Siesta Key SunBum Studio
$227 per night
Superhost
Condo in Longboat Key
Beachfront Resort, Ocean View, Pool, Tennis, Gym
$286 per night
Superhost
Condo in Bradenton Beach
Steps to beach! Gulf view, walk to Bridge St! #3
$201 per night
Superhost
Condo in Treasure Island
Directly on Beach, Stunning Views, Pool, King Bed!
$155 per night
Superhost
Condo in Longboat Key
The Beach Condo Unit #107 Beachfront
$199 per night
Superhost
Condo in Holmes Beach
Steps from the beach
$219 per night
Superhost
Condo in Siesta Key
Solitude Suite Studio-Siesta Key-Waterfront Resort
$123 per night
Superhost
Condo in Bradenton Beach
Your Tropical Paradise Destination
$175 per night
Superhost
Condo in Holmes Beach
Beach Escape - Make Memories on Anna Maria Island!
$200 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.


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.

Destinations to explore