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Vacation Rentals & Vacation Rentals in Anna Maria

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Vacation Rentals & Vacation Rentals in Anna Maria

About Anna Maria

2,980 beach rentals

Canalfront home w/ pool, dock & lanai - 2 blocks to the beach, dogs OK!

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 35 minutes

Price per night from

$193

1 / 25

Stay & Spoil yourself! Pool, Hot tub,Fish, Dock, Kayak* Steps to Gulfside beach!

Anna Maria house

4 bedrooms / 3 bathrooms / sleeps 8

“Terrific home” Beautiful, comfortable home with lovely pool and just a short walk to gulf. Pictures don't fully capture how nice this home is! Our family had a wonderful week and hope to return again.

Responds fast! avg. 2 hours 4 minutes

Price per night from

$357

1 / 23

742 Jacaranda Rd

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$200

1 / 30

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

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 1 hour 35 minutes

Price per night from

$136

1 / 29

Charming cottage w/ island views, entertainment & nearby beach access!

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 35 minutes

Price per night from

$122

1 / 33

BON AMI: 3BR Family-Friendly Pool Home

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 7

“Bliss” Villa was exactly what we were looking for infact better than what I imagined,location great all it's amenities good and very well kept and presented would recommend to others

Price per night from

$220

1 / 24

Bean Point Beach Cottage

Anna Maria cottage

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$257

1 / 23

Oceanfront dog-friendly home w/private pool & ocean view - right on the beach!

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 35 minutes

Price per night from

$429

1 / 52

Cabana- 104 29th St Unit 2, Holmes Beach

Anna Maria house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$130

1 / 18

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 M

Responds fast! avg. 49 minutes

Price per night from

$137

1 / 123

Whispering Pines: 2BR Classic Cottage Near Beach

Anna Maria cottage

2 bedrooms / 2 bathrooms / sleeps 6

“Perfectly Charming” We had the most wonderful stay at Whispering Pines, a beautiful cottage on Anna Maria Island. It couldn't have been more perfect. My parents, my two 12 year-olds and I thoroughly enjoyed this charming cottage, a few steps from the

Price per night from

$200

1 / 24

AMI Retreat: 3BR Pool Home 200 Steps from Beach

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

“Beautiful and relaxing” The property was wonderful. The house was maintained very well, the pool was clean, and it came almost fully stocked with plates,pots and pans and every day necessities that you would need. Everyone enjoyed being so comfortabl

Price per night from

$229

1 / 24

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 8 minutes

Price per night from

$400

1 / 46

A Puff Away East- 114 Magnolia Ave East, Anna Maria

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$104

1 / 18

Bright and cheery waterfront home with private pool and spa

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 35 minutes

Price per night from

$243

1 / 37

Yellowbird

Anna Maria house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$429

1 / 31

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

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 35 minutes

Price per night from

$243

1 / 29

Starfish Dreams: 2BR Canal Home w/Dock & Pool

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

“excellent week..beautiful place just what we wanted !!” loved the access to the canal and straight into the bay, had the perfect week !! House was even better than expected and AMI coastal cottages made it even better !! Loved the huge porch on back

Price per night from

$214

1 / 24

Charming 2 Bedroom/2 Bath Cottage on a Canal

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 0 minutes

Price per night from

$219

1 / 22

Bradley's Beach House: 4BR Pool Home Steps From Beach

Anna Maria house

4 bedrooms / 3 bathrooms / sleeps 8

“We enjoyed a week in paradise.” We rented the house for a family Christmas vacation. The process was easy and the staff at AMI were very helpful and friendly. The house was large enough for our family of 8 to enjoy. It was a nice surprise to arrive an

Price per night from

$335

1 / 24

Sand Castle well appointed home steps from beaches

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 29 minutes

Price per night from

$339

1 / 25

21 Palms A

Anna Maria house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$114

1 / 21

209 Spring

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$275

1 / 57

Anna Cabana B

Anna Maria bungalow

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$129

1 / 24

744 Jacaranda Rd

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 6

“Nice getaway” Nice home! Large enough for family. Decks and heated pool were great!

Price per night from

$275

1 / 32

Pelican Roost 505

Anna Maria house

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$464

1 / 33

Wave Crest: 3BR Gulf-Front Beachfront Cottage

Anna Maria cottage

3 bedrooms / 3 bathrooms / sleeps 6

“3/22-3/29 2014” Our recent stay at Wave Crest was just as pictured and described from the Coastal Cottages site. The rental came with everything to enjoy several days with children on the beach. When the time comes for us to return to aMI we will de

Price per night from

$400

1 / 25

Islands End- 792 North Shore Dr, Anna Maria

Anna Maria house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$86

1 / 12

Anna Maria's Best

Anna Maria house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$643

1 / 24

A Place in Paradise A

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$121

1 / 23

Sand Dollar- 208 76th St, Holmes Beach

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$93

1 / 28

Cast Villa 1

Anna Maria villa

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$119

1 / 35

Cute cottage with patio and amazing location near Pine St. and the beach

Anna Maria house

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 35 minutes

Price per night from

$92

1 / 28

Jacaranda Artist Retreat

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$113

1 / 17

Surfer Girl- 211 77th St

Anna Maria house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$79

1 / 22

5 Star - Private Pool & Dock, and Steps Away from the Beach - Fall Availability

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 24 minutes

Price per night from

$219

1 / 39

Seas The Day: 2BR Family Friendly Canal Home

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$171

1 / 22

Tequila Sunset: 2BR Pet-Friendly with Heated Pool

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$157

1 / 24
Viewing 38 of 2,980

About Anna Maria

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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.

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