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Vacation Rentals & Beach Rentals in Anna Maria

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2,264 beach rentals

Ocean View 3 bedroom, pool, North Shore Drive

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

“Amazing Oceanview Pool Home and Perfect Location On Anna Maria Island” Let me first say that Mark (the home owner) exceeded any and all expectations for our 15th wedding Anniversary! We booked last minute and when we wanted to stay an additional day Mark rescheduled planned maintenance in order to accommodate us. When we arrived there were fresh flowers, wine, cookies, music and a Anniversary Cake for us! The Beautiful ocean view pool home is in a perfect location on Anna Maria Island and equipped with everything you will need: floats for the pool, anything you would need to take to beach across the street, bikes to explore the island, a large kitchen stocked with everything you need to cook, very comfortable beds and spacious rooms, fresh orchids throughout the home, library of DVD's and books, and I could just keep going...make sure you take the bikes and explore - go to the Museum, to bean point, have fresh grouper sandwich at the Rod and Reel Pier, ride down to Two Scoops for an ice cream and take a walk on the City Pier, on Fridays at 12:30 you can pick up amazing fresh bread at Olive Oil Outpost with some other goodies, go have a custom snack at the Donut Experiment, A drink at the Sandbar Rest., Lunch or Dinner at the Waterfront is amazing, and more all a short bike ride away. All my wife and I can say is what a wonderful week and we will be back for sure!

Responds fast! avg. 6 minutes

Price per night from

$342

Charming cottage less than a block from the beach! free trolley trolley nearby!

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$158

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

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 0 minutes

Price per night from

$155

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

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 11 minutes

Price per night from

$228

Beautiful, well-maintained home w/private pool - walk to beach, dining, & more!

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 0 minutes

Price per night from

$331

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. 0 minutes

Price per night from

$217

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

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 0 minutes

Price per night from

$243

Bright and cheery waterfront home with private pool and spa

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$443

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

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$176

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

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$271

Dolphin Pointe

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 34 minutes

Price per night from

$296

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. 0 minutes

Price per night from

$197

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

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$185

Beautiful luxury beach front condominium

Anna Maria condo

3 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$731

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

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$262

Sea Haze Cottage - Gorgeous waterfront pool beachhouse

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$349

19 Palms. Quaint Old-Florida Charm

Anna Maria house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$162

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. 1 hour 22 minutes

Price per night from

$432

The Lime Door

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$283

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. 0 minutes

Price per night from

$202

Blue Heron Waterfront House Anna Maria island

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 45 minutes

Price per night from

$401

Anna Maria Island "High End" Vacation Rental

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 30 minutes

Price per night from

$344

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

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 19 minutes

Price per night from

$406

Dog-friendly home with private pool, great location near beach, shopping, dining

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 0 minutes

Price per night from

$120

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

Anna Maria house

3 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$224

Pier House

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$157

Sand Castle well appointed home steps from beaches

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 45 minutes

Price per night from

$458

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

Anna Maria house

6 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$547

Incredible, dog-friendly house with private heated pool, close to the beach!

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$409

Crescent Wave

Anna Maria house

4 bedrooms / 3 bathrooms / sleeps 8

“Mrs.” With three couples and three kids, this house met our needs perfectly. Great location-about three blocks from the beach, and two blocks from Pine Avenue. We didn't have to get back in the car after arriving until we left. The house was well stocked with towels, kitchenware, and even books and games for the kids. The wagon, beach buggies, beach chairs, and beach toys from the shed were all put to good use. Having a pool with three kids is a must. We enjoyed the pool area, but the pool needed some TLC. All and all it was a great vacation. We would stay at this house again!

Responds fast! avg. 1 hour 48 minutes

Price per night from

$244

The Oleander House

Anna Maria house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$360

Reduced rates for June Stunning luxury beachfront house with pool and spa

Anna Maria villa

4 bedrooms / 5 bathrooms / sleeps 8

“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.

Price per night from

$814

Charming 2 Bedroom/2 Bath Cottage on a Canal

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$310

Luxury waterfront home w/ private pool and dock only three blocks to beach!

Anna Maria house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$304

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

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$280

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

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 0 minutes

Price per night from

$250

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

$218

Viewing 38 of 2,264
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

Crescent Wave
Absolutely wonderful!!

This house is even better than it looks in the pictures .... everything you might want or need while on vacation is provided. It was extremely clean, and the location is perfect. The center across the street is a real bonus with "snow bird" deals. The pool and backyard of this house are beautiful, with plenty of seating and heated pool. We had an issue with the heat in the pool and owner, Rick, responded asap and got it repaired the same afternoon. He then followed up to make sure everything was working. House is very well-stocked from the kitchen to the pool, with lots of beach equipment provided as well. And the two master suites on either end of the house are very convenient.see more
Anna Maria Island "High End" Vacation Rental
Excellent

Beautiful place, secluded and private. Very clean and Pet friendly. Could not ask for anything more. … see more
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
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
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

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