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Vacation Rentals & Beach Rentals in Anna Maria

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2,184 beach rentals

Spacious house w/ private yard & great location near the beach - dogs ok!

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 57 minutes

Price per night from

$197

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

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

“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.

Price per night from

$460

Beautiful, well-maintained home w/ heated private pool - walk to beach, dining

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 57 minutes

Price per night from

$345

Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK!

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 57 minutes

Price per night from

$235

Waterfront dog-friendly home with heated private pool, dock, views, and lanai!

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 57 minutes

Price per night from

$361

Holmes Beach Home w/Pool & Hot Tub, Walk to Beach!

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 8 minutes

Price per night from

$314

Breezy canalfront home w/ heated pool & dock - 3 blocks to Bean Point Beach!

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 57 minutes

Price per night from

$318

Charming house with private heated pool, patio, and grill - steps from beach

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 57 minutes

Price per night from

$280

Dolphin Pointe

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 27 minutes

Price per night from

$410

Sunny, dog-friendly cottage w/ a spacious patio and grill, steps from the beach!

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 57 minutes

Price per night from

$212

Dog-friendly house with heated private pool, island views & nearby beach access!

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 57 minutes

Price per night from

$227

Beautiful luxury beach front condominium

Anna Maria condo

3 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$827

Oceanfront house with great views, easy beach access, and free WiFi

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 57 minutes

Price per night from

$638

Sea Haze Cottage - Gorgeous waterfront pool beachhouse

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$345

19 Palms. Quaint Old-Florida Charm

Anna Maria house

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 7 minutes

Price per night from

$184

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.

Responds fast! avg. 3 hours 9 minutes

Price per night from

$511

Dog-friendly condo w/ beautiful upstairs deck and grill, steps from the beach

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 57 minutes

Price per night from

$228

Blue Heron Waterfront House Anna Maria island

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 26 minutes

Price per night from

$447

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

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 22 minutes

Price per night from

$447

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

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 57 minutes

Price per night from

$257

High-end home w/heated private pool & spa, courtyard, & floor-to-ceiling windows

Anna Maria house

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 1 hour 57 minutes

Price per night from

$365

Pier House

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$158

Sand Castle well appointed home steps from beaches

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 26 minutes

Price per night from

$515

Full duplex w/ private heated pool and fenced backyard - dogs welcome!

Anna Maria house

6 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 57 minutes

Price per night from

$556

Incredible, spacious home with a private heated pool - close to the beach!

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 57 minutes

Price per night from

$440

Stunning luxury beachfront house with pool and spa

Anna Maria villa

4 bedrooms / 5 bathrooms / sleeps 8

“Great Accommodations” Hi Nigel and Maggie. We have enjoyed your place 3 weeks this year. Had one week in January and the other 2 in Feb/Mar. We could hardly wait to go back after our first week. The property manager was attentive and offered his help for anything we needed. We loved the house, especially the elevator when I arrived alone with all the luggage and groceries. Life saver! The views are spectacular and the privacy was especially nice too. The house is among other homes but still private at the same time. We especially loved the green space between the house and the beach......rustic and natural. If I don't get my husband to build me a house like this, we will be back!!!

Price per night from

$804

Luxury waterfront home w/ heated private pool & dock only three blocks to beach

Anna Maria house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 1 hour 57 minutes

Price per night from

$621

Dog-friendly duplex w/ shared heated pool - one block to the beach

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 57 minutes

Price per night from

$289

Beautiful cottage w/ heated private pool - walk to beach, dining, Bayfront Park

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 57 minutes

Price per night from

$283

Brand New Renovation Sea Waves Cottage

Anna Maria cottage

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$217

Newly renovation bay side cottage: Sea Breeze

Anna Maria cottage

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$217

Gladiolus on the Water

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$293

Dog-friendly house w/ private, heated pool & entertainment - walk to the beach!

Anna Maria house

5 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 57 minutes

Price per night from

$472

Latitude Adjustment

Anna Maria log cabin

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$158

Gladiolus House

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$180

Canalfront Anna Maria Cottage w/ Pool & Hot Tub!

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 8 minutes

Price per night from

$355

Dog-friendly house w/ heated private lagoon pool - two blocks from the beach!

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 57 minutes

Price per night from

$304

Canal-front home with private dock, covered lanai with heated pool and grill

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 57 minutes

Price per night from

$302

Viewing 38 of 2,184
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

Brand New Renovation Sea Waves Cottage
Excellent

We loved the accomadations and the location was great.everything we needed was there. The place was 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
Newly renovation bay side cottage: Sea Breeze
Adorable

Wonderful location, cottage was as promised. The water view is very peaceful. Great restaurants and activities within biking distance. We rented bicycles for the week and hardly had to use the car. … see more
Stunning luxury beachfront house with pool and spa
Fabulous beach house

After a mad week doing the theme parks in Orlando we came here for some serious relaxation - and what a great choice it was. The house is stunning and the location couldn't be bettered. Living on the beach meant we could be up for early morning shell hunts and then have evening strolls to the Sandbar for cocktails on the sand watching the glorious sunsets. We saw dolphins, manatees, rays and pelicans. The pool area got a lot of use - a nice shady retreat and good fun for our boys - but most of our time was spent outside. There are lots of lovey restaurants to walk to - the Waterfront, the Sandbar, the two pier restaurants - and you can walk there on the sand. Still picturing the crystal clear sea, sunny skies and white sand. Magical.see more
Beachfront Paradise w/ Private Beach, Dogs Stay Free, Beach in Backyard
Wonderful place for relaxation

Incredible location with it's own private beach. Great laid back part of the island. Lots to do if you want to, or just relax and take in the natural beauty of the gulf. Accomodations for large family or group of friends. Plenty of parking. Comfortable beds and furniture. Clean house. Very nice owners and permit pets to be a part of the fun. Recommend to anyone looking for a vacation Anna Maria island. Short walk to the island public beaches too if that's what someone is looking for.see more
Dolphin Pointe
Great house!

The house was perfect; great open living room and kitchen and the pool was so fun. The location was great; close to the beach and lots of things to do. … see more

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