Discover a selection of 3,500 vacation rentals in Anna Maria, FL that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and kitchens. Prices start at $180 per night, and houses and cottages are popular options for a stay in Anna Maria. Either way, you'll find a rental for everyone's needs.
Destination guide

With beaches and fun activities, you’ll love Anna Maria

Visitors to Anna Maria Island always find a fun vacation haven, perfect for kayaking and experiencing island life. Tucked away on Anna Maria’s north end is Bean Point Beach, ideal for those seeking an island paradise with an Old Florida vibe. Anna Maria Bayfront Park offers sweeping views of Tampa Bay, and in addition to its beaches is also home to numerous restaurants. Spend your afternoons with your toes in the sand or shopping till you drop—either way, your Anna Maria vacation rental gives you access to a getaway the whole family will enjoy.

Things to do

Immerse yourself in the Anna Maria experience

The beaches are just one reason to book an Anna Maria vacation rental. The island boasts museums as well as restaurants serving everything from fresh seafood to specialty cupcakes and donuts. Take a stroll on the pier—or down Pine Avenue with its colorful, eclectic shops. It’s not every day you get to soar hundreds of feet over the ocean, so if you’re feeling brave, try parasailing. If staying in the water is more your speed, check out Bean Point, and keep an eye open for manatees, which are known to mingle with human swimmers.


Pack the sunscreen—there’s lots to do in Anna Maria

Anna Maria vacation rentals are perfect if you love the beach. There are endless entertainment options for those who love the sun, sand, and water. Rent Segways for the family and tour the island in style. Go on a sightseeing dolphin cruise, or have some high-powered fun on a jet ski. Spend hours relaxing on the beach, or keep things active and sign up for a kayak lesson or tour. Paddleboard rentals, boat trips, fishing excursions and more are yours for the taking when you book a vacation rental in Anna Maria.


Expect pleasant weather any time of the year

Anna Maria has sun, sand, beautiful beaches, and exceptional weather. The climate is warm and temperate with plentiful rainfall, and when it does rain, it’s often short-lived before the clear blue skies return. Most of the year sees abundant sunshine, and in the heart of summer, the average high is a pleasant 88 degrees. Winter is mild with an average January low of 52. The best time to book a vacation rental in Anna Maria depends on what you’d like to do, but even winter is typically comfortable enough for outdoor activities.

Natural features

Diverse wildlife and island beauty in Anna Maria

Anna Maria is a bird sanctuary. Cranes, pelicans, herons, sandpipers, parrots, seagulls, vultures, and crows all call the island home. Marine life includes bottlenose dolphins, snapper, redfish, mackerel, and amberjack. Anna Maria lies adjacent to the isle of Key Royale, which was uninhabited until 1960 when a new bridge joined it to Anna Maria. At the southern edge of Anna Maria lies Longboat Key, and Jewfish Key is situated just to the east of the connecting drawbridge. Book your vacation rental in Anna Maria to see for yourself all this beautiful island offers.

How to get there

Transportation options to and around Anna Maria

Fly into Sarasota, FL (SRQ-Sarasota-Bradenton Intl.), the closest airport, located 14.7 mi (23.7 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into St. Petersburg, FL (SPG-Albert Whitted), which is 17.4 mi (28 km) away.

How many vacation rentals are available around Anna Maria, FL?

Our 2020 property listings offer a large selection of 3,619 vacation rentals around Anna Maria. From 1,680 house rentals to 170 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What is the best area to stay when traveling to Anna Maria?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Anna Maria:

  • Sunset Beach: 1,318 vacation rentals
  • Lido Key: 1,889 vacation rentals
  • Isla del Sol: 289 vacation rentals
  • Ilexhurst: 1,463 vacation rentals
  • Pass-a-grille: 190 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular point of interests near where I can stay when traveling to Anna Maria?

Vrbo offers a large selection of vacation rentals near lovely places in Anna Maria. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Anna Maria Island Museum and Historical Park: 7,682 vacation rentals
  • AMI Outfitters Coastal Gear & Apparel: 7,701 vacation rentals
  • Island Players: 7,676 vacation rentals
  • Historic Green Village: 7,751 vacation rentals
  • St. Armands Circle: 8,240 vacation rentals

But there are many other points of interest around Anna Maria listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Anna Maria?

Yes, of course. Vrbo has 1,680 Houses in Anna Maria. Our other popular types of vacation rentals in Anna Maria include:

  • Cottages: 170 rentals available
  • Bungalows: 170 rentals available
  • Condos/Apartments: 1,398 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Villas and more.

Can I find a vacation rental with pool in Anna Maria?

Yes, you can select your preferred vacation rental with pool among our 2,895 vacation rentals with pool available in Anna Maria. Please use our search bar to access the selection of vacation rentals available.

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