Vacation Rentals & Beach Rentals in Anna Maria

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1,360 beach rentals

Beachfront Paradise w/ Private Beach, Dogs Stay Free, Beach in Backyard

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$630

Gorgeous views,spectacular home!

Anna Maria house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

“Majestic Views” Our family loved our visit to Anna Maria. The house is gorgeous and spacious. My kids enjoyed the pool and eating outside. We hope to return in the near future.

Price per night from

$584

Enjoy our Beach, Pool and Dock! 100 5-Star Reviews!

Anna Maria house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$744

Sea Waves in Anna Maria Island with Private Dock

Anna Maria cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$377

Newly renovation bay side cottage: Sea Breeze

Anna Maria cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$354

Mango Beach House - Unforgettable vacations and sunsets

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$630

Jacaranda Artist Retreat

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$218

"Island Oasis" A single family North end canal home with pool

Anna Maria house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$745

Serendipity Deux- Beachfront 4 Bed/heated pool/elevator

Anna Maria house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Price per night from

$2,290

Going Coastal

Anna Maria house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$294

Coconut Cove

Anna Maria house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$476

The Salty Dog on North Shore

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 28 minutes

Price per night from

$389

Anchor Splash

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$619

Island Getaway

Anna Maria house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$344

Island Memories

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$453

Blue Lagoon South

Anna Maria house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$275

Serendipity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$1,260

C View

Anna Maria house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$573

White Sand Beaches- Bayfront Park

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$630

Luxury waterfront home with a heated pool and spa!

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 28 minutes

Price per night from

$537

Manatee Retreat

Anna Maria house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Price per night from

$401

FantaSea

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$1,489

SeaTurtle Escape

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$802

Coastal Serenity

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$573

Bimini Cove

Anna Maria house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

Price per night from

$62

Manatee Retreat Unit B

Anna Maria house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Price per night from

$277

Blue Lagoon North

Anna Maria house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$275

Stonehenge

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$539

Waves on Anna Maria

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$974

Cloud 9

Anna Maria house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 8

Price per night from

$1,947

Manatee Retreat Unit A

Anna Maria house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

Price per night from

$277

Blue Lagoon

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Price per night from

$550

Simpatico

Anna Maria house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$409

Coconut Breeze Estate

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Price per night from

$670

Manatee Lookout

Anna Maria house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$390

Seaglass Cottage

Anna Maria log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$315

Anna Maria Beach Serenity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 39 minutes

Price per night from

$1,185

Copacabana Boaters Dream Home in Anna Maria

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 28 minutes

Price per night from

$416

Viewing 38 of 1,360
rentals in Anna Maria

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About Anna Maria

Anna Maria, Florida

The palm and hibiscus-lined streets of Anna Maria Island exude a relaxed, 1950s-style charm that attracts visitors all year round. Whether you come to laze on the white sandy beaches or explore all the area has to offer, you’re sure to find your perfect Anna Maria vacation rental with FlipKey.

About Anna Maria

Anna Maria Island was discovered by Native Americans and later by Spanish explorers in 1539. But the island wasn’t settled until the start of the 20th century, and it wasn’t until 1921 that a bridge was built, connecting the island to the mainland.

Today, this relaxed island is home to three main towns: Bradenton Beach, Holmes Beach and Anna Maria. You’ll find some of the best beaches to the north and south of the island, and it’s just a one hour drive to Tampa, or two hours to Orlando and Disney.

Dine on the freshest seafood, from Grouper, Shrimp, Mahi-Mahi and Lobster to Blue Crab and Red Snapper. You’ll also find great sushi, and excellent Italian and Mexican food on offer at seafront restaurants. Wash it all down with a glass of Florida orange juice – Tropicana is produced here in Bradenton!

What to do

There’s plenty to see and do here, but why not relax on the white sandy beaches that run the whole length of the island (7 miles)? The best beaches are Anna Maria Bayfront Park, and Southern Coquina Beach with its family-friendly facilities.

Rent a boat or go on a charter fishing trip with the family, or explore the coastline in a kayak or boat. Diving, snorkeling and parasailing are all popular activities, or you could even go canoeing at Myakka State Park, where you’ll spot wild boar and alligators.

A stroll around Anna Maria Island Museum is the opportunity to uncover local history, or people-watch at one of the island’s piers. Anna Maria City Pier is the place to see cruise ships leaving Tampa Bay and fishermen with their catch of the day, as well as stunning views of the Skyway Bridge.

Top Anna Maria travel tips

Anna Maria is just a one hour (53 miles) drive from Tampa International Airport, whilst Sarasota-Bradenton International Airport is 18 miles away.

It’s easy to get around thanks to a free trolley service which runs from 6am-10pm daily, covering the whole of the island.

Traffic limits of around 25mph in most areas mean that Anna Maria is a family-friendly destination, great for renting a bike or walking and exploring.

Average temperatures of 80-90 degrees Fahrenheit ensure summer is the most popular season, but spring and fall are still warm (although evenings can be cooler).

Sun, sea, sand, delicious seafood and plenty of outdoor activities for the whole family – what’s not to love?

With over 1,000 cozy cottages, beachfront condos and villas to choose from, browse FlipKey for your Anna Maria vacation rental, today.

Top Destination reviews

Sea Waves in Anna Maria Island with Private Dock
Excellent

We loved the accomadations and the location was great.everything we needed was there. The place was beautiful … see more
Beachfront Paradise w/ Private Beach, Dogs Stay Free, Beach in Backyard
Love this place

We absolutely loved our stay at the beach house. It was perfect for us and our two dogs. If you love wildlife it is perfect. Many birds and several dolphins were seen Several crabs on our beach. Plan on coming back next year. The morning sunrises were beautiful. … see more
Gorgeous views,spectacular home!
Nice needed some better cleaning

House was in a great location. Plenty of room. Needed better cleaning and some minor repairs. We would stay again though. … see more

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