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Vacation rental beach houses in Anna Maria

Book beachfront vacation rental houses, cottages, and more on Airbnb

Top-rated houses in Anna Maria

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

Anna Cabana B
SUPERHOST
Entire house · 4 guests · 1 bed · 1 bath

Anna Cabana BAnna Cabana B is the perfect getaway, it has it's own private pool, patio, private entrance and driveway. A queen bedroom and a sofa bed will accommodate four, or it is just perfect for a getaway for two! Fully updated kitchen allows you to whip up a fabulous meal or perhaps the outside gas grill will entice you to grill up some freshly caught fish. This property also features professional linen service. Landscaping and fence provide plenty of privacy. Unit is a duplex with Anna CabanaA

Charming house w/heated pool,steps to beach-Unit A
SUPERHOST
Entire house · 4 guests · 3 beds · 1 bath

Charming house w/heated pool,steps to beach-Unit ALocation! North end of Anna Maria Island . This charming two story duplex- each unit has two bedrooms , one bathroom. Rent one unit or both. Perfect for a group of extended family and friends who want their own place but still be right together as a group. Heated inground pool, steps to the Bean Point Beach . Includes beach chairs, umbrellas and all you need for a perfect day at the beach! Heated pool , private seating, grilling areas, bicycles and much more available.

⭐️Escape to Anna Maria ⭐️ fischervacationrentals
SUPERHOST
Entire house · 6 guests · 5 beds · 2 baths

⭐️Escape to Anna Maria ⭐️ fischervacationrentalsWelcome to paradise! ANNA MARIA ISLAND is the first of the barrier islands located along Florida's Gulf Coast. It is about 7 miles long and 1/2 a mile wide. It is known for beautiful beaches, breathtaking sunsets and a boat load of really nice people. The number one activity in the area is to DO NOTHING AND RELAX ON THE BEACH.

Vacation rentals for every style

Get the amount of space that is right for you

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Popular house amenities in Anna Maria

  • Pool
  • Pets allowed
  • Air conditioning
  • Kitchen
  • Wifi

Cottages in Anna Maria

SUPERHOST
  1. Entire cottage
  2. Anna Maria
Turtle Cottage - Anna Maria Island
$199 per night
SUPERHOST
  1. Entire cottage
  2. Anna Maria
Adorable Pine Ave Cottage ❤️Walk to Beach and Bay!
$191 per night
SUPERHOST
  1. Entire cottage
  2. Bradenton Beach
The Anchor Cottage 2
$175 per night
  1. Entire cottage
  2. Anna Maria
The Barefoot Gypsy-Quaint remodeled beach cottage
$283 per night
  1. Entire cottage
  2. Bradenton Beach
50 Steps to Beach🏖. Hot Tub! 1bd modern cottage🏝
$295 per night
  1. Entire cottage
  2. Bradenton
Starfish Cottage Walk to beach, 8+eateries & bars
$106 per night
SUPERHOST
  1. Entire cottage
  2. Holmes Beach
Cozy Cottage by the Beach sleeps 6 - Seascape
$185 per night
SUPERHOST
  1. Entire cottage
  2. Bradenton Beach
Tides Inn 2 on the Bay
$161 per night
SUPERHOST
  1. Entire cottage
  2. Anna Maria
MorSea Cottage: A Beachside Oasis
$358 per night
SUPERHOST
  1. Entire cottage
  2. Holmes Beach
Tropical Oasis so Close to Beach and Pet Friendly!
$171 per night
  1. Entire cottage
  2. Bradenton Beach
Darling "Cottage" Just Steps From The Gulf!
$220 per night
SUPERHOST
  1. Entire cottage
  2. Cortez
Ty's Canal Cottage
$89 per night

Pet-friendly houses

  1. Entire house
  2. Holmes Beach
Beach Chic! Ensuite bathrooms with a yard.
$135 per night
  1. Entire house
  2. Anna Maria
Tripletail
$800 per night
  1. Entire house
  2. Anna Maria
Dog-friendly home w/heated private pool, near beach, shopping, dining
$264 per night
SUPERHOST
  1. Entire house
  2. Holmes Beach
Ohana Hale North 1 Bedroom
$136 per night
SUPERHOST
  1. Entire house
  2. Holmes Beach
AMI Starfish
$312 per night
SUPERHOST
  1. Entire house
  2. Anna Maria
AMI Boathouse
$479 per night
SUPERHOST
  1. Entire house
  2. Holmes Beach
Sea AMI
$230 per night
SUPERHOST
  1. Entire house
  2. Anna Maria
⭐️ Seaside Sanctuary ⭐️ fischervacationrentals
$166 per night
SUPERHOST
  1. Entire house
  2. Bradenton
2/1 duplex w/access to shared ramp, <2miles to AMI
$195 per night
  1. Entire house
  2. Bradenton Beach
Sugar Sunsets AMI -Unit B. Steps to the beach!
$273 per night
SUPERHOST
  1. Entire house
  2. Bradenton
Paradise Found Family & Friends Retreat
$249 per night
SUPERHOST
  1. Entire house
  2. Bradenton Beach
The Anna Maria Beach Cottage - East
$178 per night

Houses with pools

SUPERHOST
  1. Entire house
  2. Holmes Beach
Anna Maria Island Duplex w/ private pool (side B)
$240 per night
SUPERHOST
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  2. Holmes Beach
Spectacular home 700 feet from the beach!
$215 per night
SUPERHOST
  1. Entire house
  2. Anna Maria
3 & 5 Day Availability August / 5-Star Property!
$330 per night
  1. Entire house
  2. Holmes Beach
Unit B - Escape to Serenity
$350 per night
SUPERHOST
  1. Entire house
  2. Anna Maria
Paddle Board Canal, Walk to Beach, Heated Pool
$375 per night
SUPERHOST
  1. Entire house
  2. Holmes Beach
A100 step to the sugar sand gulf front view & pool
$300 per night
SUPERHOST
  1. Entire house
  2. Anna Maria
AMI Retreat
$378 per night
SUPERHOST
  1. Entire house
  2. Holmes Beach
Private, Comfy, Close to the Beach w/ heated pool
$298 per night
SUPERHOST
  1. Entire house
  2. Bradenton Beach
Exquisite Private Pool Elevator Beach/Bay views
$599 per night
SUPERHOST
  1. Entire house
  2. Anna Maria
White Pearl-New Premier AMI Home with Sunset Views
$749 per night
SUPERHOST
  1. Entire house
  2. Holmes Beach
Luxury 3BR/3BA, Private Heated Pool, Beach
$278 per night
  1. Entire house
  2. Longboat Key
North Longboat Key Beach Retreat
$500 per night

All About Anna Maria Island

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 book a Anna Maria Island vacation rental?

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 for a sunny 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.

Anna Maria Island Historical Society Museum Complex

Home to a former icehouse converted to a museum and a restored cottage built in 1920, many visitors flock to this site to snap a quirky photo at the island’s former jail, built in 1927. Its wooden roof burned in 1940, and since then it’s been reborn as a kitschy photo op.

Nearby destinations