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Anna Maria Rentals

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Anna Maria Rentals

About Anna Maria

156 beach rentals

Discount July 4th week! Pool, Hottub,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 7 minutes

$357

1 / 23

21 Palms A

Anna Maria house

2 bedrooms / 1 bathroom / Sleeps 4

$114

1 / 21

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 25 minutes

$136

1 / 29

Jacaranda Artist Retreat

Anna Maria house

3 bedrooms / 2 bathrooms / Sleeps 6

$113

1 / 17

742 Jacaranda Rd

Anna Maria house

3 bedrooms / 2 bathrooms / Sleeps 6

$200

1 / 30

A Place in Paradise B

Anna Maria house

2 bedrooms / 2 bathrooms / Sleeps 6

$121

1 / 23

BEACHFRONT HOME, TRUE PARADISE , DOGS STAY FREE, GREAT VIEWS, WALKING BEACH

Anna Maria house

3 bedrooms / 2 bathrooms / Sleeps 8

Responds fast! avg. 33 minutes

$175

1 / 22

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. 55 minutes

$237

1 / 123

Cast Villa 1

Anna Maria villa

2 bedrooms / 1 bathroom / Sleeps 6

$119

1 / 35

209 Spring

Anna Maria house

3 bedrooms / 2 bathrooms / Sleeps 8

$275

1 / 57

Anna Maria Island "High End" Vacation Rental

Anna Maria house

2 bedrooms / 2 bathrooms / Sleeps 6

“Excellent” Beautiful place, secluded and private. Very clean and Pet friendly. Could not ask for anything more.

$200

1 / 21

Sand Castle well appointed home steps from beaches

Anna Maria house

3 bedrooms / 2 bathrooms / Sleeps 8

Responds fast! avg. 2 hours 21 minutes

$299

1 / 25

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 21 minutes

$193

1 / 25

Dolphin Pointe

Anna Maria house

3 bedrooms / 3 bathrooms / Sleeps 8

Responds fast! avg. 1 hour 0 minutes

$257

1 / 39

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

$220

1 / 24

Anna Maria's Coconut Breeze Estate - no cleaning fee

Anna Maria house

4 bedrooms / 4 bathrooms / Sleeps 10

Responds fast! avg. 3 hours 28 minutes

$929

1 / 50

Pineapple Cottage: 2BR Quaint Pet-Friendly Cottage

Anna Maria cottage

2 bedrooms / 1 bathroom / Sleeps 6

“Fall vacation” The weather was nice several of the days and we really enjoyed less people than we encounter in July. Lots of beach walks and bike rides. My only issues were the dirty rug in dining area and flat pillows on all of the beds.

$171

1 / 21

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!

$250

1 / 32

Gorgeous views,spectacular home!

Anna Maria house

5 bedrooms / 3 bathrooms / Sleeps 12

“Awesome!” This house was awesome with it's fabulous views from the decks! Very spacious rooms especially the master bedroom!

Responds fast! avg. 1 hour 16 minutes

$406

1 / 46

Little Slice of Paradise: 2BR Canal-Front Condo

Anna Maria apartment

2 bedrooms / 1 bathroom / Sleeps 4

$96

1 / 24

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 22 minutes

$119

1 / 28

The Lime Door

Anna Maria house

2 bedrooms / 2 bathrooms / Sleeps 6

$243

1 / 29

Bright and cheery waterfront home with private pool and hot tub

Anna Maria house

3 bedrooms / 3 bathrooms / Sleeps 6

Responds fast! avg. 1 hour 25 minutes

$243

1 / 37

Grandview: 3BR Family-Friendly Home

Anna Maria house

3 bedrooms / 3 bathrooms / Sleeps 6

$214

1 / 27

Bayou 5B

Anna Maria apartment

2 bedrooms / 1 bathroom / Sleeps 4

$107

1 / 19

A Place in Paradise A

Anna Maria house

2 bedrooms / 2 bathrooms / Sleeps 6

$121

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 21 minutes

$350

1 / 52

116 Maple Breeze

Anna Maria house

4 bedrooms / 2 bathrooms / Sleeps 7

$229

1 / 24

Charming 2 Bedroom/2 Bath Cottage on a Canal

Anna Maria house

2 bedrooms / 2 bathrooms / Sleeps 4

Responds fast! avg. 1 hour 31 minutes

$219

1 / 22

Island Place Cottage: 1BR Pet-Friendly Cottage

Anna Maria cottage

1 bedroom / 1 bathroom / Sleeps 2

“Perfect!” We stayed here for two weeks, January 2014. It is well located, spotless and adorable. Everything you need for a perfect vacation on the island ... we didn't want to leave!

$136

1 / 23

Cast Villa 2

Anna Maria villa

2 bedrooms / 1 bathroom / Sleeps 6

$119

1 / 20

5 Star - Private Pool & Dock - May Availability - Special Pricing

Anna Maria house

3 bedrooms / 3 bathrooms / Sleeps 8

Responds fast! avg. 1 hour 24 minutes

$219

1 / 39

4 bed luxury upscale executive waterfront home

Anna Maria house

4 bedrooms / 4 bathrooms / Sleeps 8

“Relaxing, Fun, Fully equipped and great location.” Loved the house it has an elevator since I have really bad knees it was great. I hope to rent it again. I wish I could have used all the equipment they had like the kayaks but my knees are way to ba

$293

1 / 50

A Mermaid's Lair

Anna Maria cottage

2 bedrooms / 2 bathrooms / Sleeps 4

$171

1 / 23

Island Time

Anna Maria house

2 bedrooms / 2 bathrooms / Sleeps 4

$171

1 / 25

Charming cottage w/ free WiFi just two blocks from the beach, near free trolley!

Anna Maria house

3 bedrooms / 2 bathrooms / Sleeps 8

Responds fast! avg. 1 hour 25 minutes

$136

1 / 24

Bean Point Beach Cottage

Anna Maria cottage

3 bedrooms / 2 bathrooms / Sleeps 6

$257

1 / 23

Anna Cabana B

Anna Maria bungalow

1 bedroom / 1 bathroom / Sleeps 4

$129

1 / 24
Viewing 38 of 156

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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