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Vacation rental beach houses in Anna Maria

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.

Dog-friendly home w/heated private pool, near beach, shopping, dining
Entire house · 6 guests · 3 beds · 2 baths

Dog-friendly home w/heated private pool, near beach, shopping, diningSea Shack

Cozy Beachhouse 800 steps to beach
Entire house · 3 guests · 1 bed · 1 bath

Cozy Beachhouse 800 steps to beachThis 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.

Luxury 3BR/3BA, Private Heated Pool, Beach
SUPERHOST
Entire house · 6 guests · 5 beds · 3 baths

Luxury 3BR/3BA, Private Heated Pool, BeachRenovated and professionally decorated single family home that sleeps 8. 3 bedrooms and 3 full bathrooms. Living room with pullout couch as well as games, books and movie library. Luxurious heated pool with waterfall and Tiki table in private tropical backyard. Large covered lanai with TV, mini-fridge, granite counter for food preparation and gas BBQ. Large size Washer/Dryer. 4 minute easy stroll to beach. Attached garage. Low traffic street. Tons of toys as well as pool and beach supplies.

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

Turtle Cottage - Anna Maria Island
SUPERHOSTEntire cottage
Turtle Cottage - Anna Maria Island
Adorable Pine Ave Cottage ❤️Walk to Beach and Bay!
SUPERHOSTEntire cottage
Adorable Pine Ave Cottage ❤️Walk to Beach and Bay!
Beautiful, well-maintained home w/ heated private pool - walk to beach, dining
Entire cottage
Beautiful, well-maintained home w/ heated private pool - walk to beach, dining
Becker's Beach Bungalow
SUPERHOSTEntire cottage
Becker's Beach Bungalow
Rest & Relax — Just One House Off The Beach
SUPERHOSTEntire cottage
Rest & Relax — Just One House Off The Beach
50 Steps to Beach🏖.  Hot Tub! 1bd modern cottage🏝
SUPERHOSTEntire cottage
50 Steps to Beach🏖. Hot Tub! 1bd modern cottage🏝
Bay Breeze Cottages #2
SUPERHOSTEntire cottage
Bay Breeze Cottages #2
Starfish Cottage Walk to beach, 8+eateries & bars
Entire cottage
Starfish Cottage Walk to beach, 8+eateries & bars
Beach Cottage with private garden
SUPERHOSTEntire cottage
Beach Cottage with private garden
MorSea Cottage: A Beachside Oasis
Entire cottage
MorSea Cottage: A Beachside Oasis
Darling "Cottage" Just Steps From The Gulf!
Entire cottage
Darling "Cottage" Just Steps From The Gulf!
Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK!
Entire cottage
Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK!

Pet-friendly houses

Anna Maria Island Duplex w/ private pool (side B)
SUPERHOSTEntire house
Anna Maria Island Duplex w/ private pool (side B)
5 STARS! Tropical Salt H2O Pool, Steps to BEACH!!
SUPERHOSTEntire house
5 STARS! Tropical Salt H2O Pool, Steps to BEACH!!
Dog-friendly beach bungalow with private, heated pool, balcony, and lanai
Entire house
Dog-friendly beach bungalow with private, heated pool, balcony, and lanai
Island in the Sun
SUPERHOSTEntire house
Island in the Sun
AMI Boathouse
SUPERHOSTEntire house
AMI Boathouse
AMI Retreat
SUPERHOSTEntire house
AMI Retreat
⭐️ Seaside Sanctuary ⭐️ fischervacationrentals
SUPERHOSTEntire house
⭐️ Seaside Sanctuary ⭐️ fischervacationrentals
⭐️Escape to Anna Maria ⭐️ fischervacationrentals
SUPERHOSTEntire house
⭐️Escape to Anna Maria ⭐️ fischervacationrentals
Casa Azul - sparkling 3 bd home, fun interior, private pool, near beach!
Entire house
Casa Azul - sparkling 3 bd home, fun interior, private pool, near beach!
Dog friendly oasis with heated private pool and very close to the beach
Entire house
Dog friendly oasis with heated private pool and very close to the beach
Salty Dogs  House- Private House w/ Pool and Spa.
SUPERHOSTEntire house
Salty Dogs House- Private House w/ Pool and Spa.
Top-rated Anna Maria, Florida Vacation Rental
SUPERHOSTEntire house
Top-rated Anna Maria, Florida Vacation Rental

Houses with pools

Canalfront home w/ heated pool, dock & lanai - 2 blocks to the beach!
Entire house
Canalfront home w/ heated pool, dock & lanai - 2 blocks to the beach!
Spectacular home 700 feet from the beach!
SUPERHOSTEntire house
Spectacular home 700 feet from the beach!
Captain's Quarters at Spinnakers Vacation Cottages
SUPERHOSTEntire house
Captain's Quarters at Spinnakers Vacation Cottages
Walk 2 Beach + PRIVATE Pool with TIKI + Golf Cart
Entire house
Walk 2 Beach + PRIVATE Pool with TIKI + Golf Cart
Canalfront Anna Maria Cottage w/ Pool & Hot Tub!
Entire house
Canalfront Anna Maria Cottage w/ Pool & Hot Tub!
5 star reviews- May & limited Summer availability!
SUPERHOSTEntire house
5 star reviews- May & limited Summer availability!
Lovely home w/ private heated pool, spa, several balconies-walk to beach/trolley
Entire house
Lovely home w/ private heated pool, spa, several balconies-walk to beach/trolley
BEACH NEST *Pool*Hot Tub*Dock*Steps to Gulf Beach!
SUPERHOSTEntire house
BEACH NEST *Pool*Hot Tub*Dock*Steps to Gulf Beach!
Elevated beach cottage with heated private pool, short walk from the beach
Entire house
Elevated beach cottage with heated private pool, short walk from the beach
Happy Island Cottage - Heated Pool
Entire house
Happy Island Cottage - Heated Pool
100 steps  to Beach
SUPERHOSTEntire house
100 steps to Beach
New Prof Decorated-Pool/Spa 5 minute walk 2 Ocean
SUPERHOSTEntire house
New Prof Decorated-Pool/Spa 5 minute walk 2 Ocean

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.

Getting There

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.

Weather

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.

Don't Miss

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