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Vacation Rentals & Beach Rentals in Anna Maria

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Vacation Rentals & Beach Rentals in Anna Maria

About Anna Maria

3,121 beach rentals

Surfer Girl- 211 77th St

Anna Maria house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$79

1 / 22

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

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$136

1 / 29

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

$117

1 / 123

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

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$429

1 / 52

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 24 minutes

Price per night from

$356

1 / 23

Crescent Wave

Anna Maria house

4 bedrooms / 3 bathrooms / sleeps 8

“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 w

Responds fast! avg. 1 hour 29 minutes

Price per night from

$200

1 / 44

Cedar Getaway Apartment- 102 Cedar Ave Apt., Anna Maria

Anna Maria house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$93

1 / 17

Sandy Toes- 116 Palmetto Ave, Anna Maria

Anna Maria house

2 bedrooms / 1 bathroom / sleeps 4

“Delightful” With the exception of a small water tank and limited hot water this was a delight and joyful cottage to call home for a week. Loved the location and the availability of beach chairs and towels. Will return.

Price per night from

$100

1 / 16

The Casita- 699 North Shore Dr, Anna Maria

Anna Maria house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$104

1 / 21

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

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$130

1 / 34

Dolphin Pointe

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 1 minutes

Price per night from

$242

1 / 39

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

Anna Maria house

1 bedroom / 1 bathroom / sleeps 4

“Great location” I was a little hesitant to rent this property because I couldn't find any reviews, but it turned out to be a good choice. It's only 4 houses away from the beach, lots of great little restaurants nearby! Don't bother going to the Sandba

Price per night from

$93

1 / 17

Life is Good at the Beach: Beautiful Home With Salt Water Pool, Walk to Beach!

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$232

1 / 22

Island Place Cottage: Beautiful Pet-Friendly Cottage On Historic Pine Ave!

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!

Price per night from

$136

1 / 23

Seas The Day: Beautiful Canal Home With A Private Deep Water Dock!

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$171

1 / 22

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

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$136

1 / 30

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

Anna Maria house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$64

1 / 28

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

$358

1 / 35

Cast Villa 1

Anna Maria villa

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 54 minutes

Price per night from

$119

1 / 35

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 11 minutes

Price per night from

$398

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

Jacaranda Artist Retreat

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$113

1 / 17

742 Jacaranda Rd

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$186

1 / 30

Yellowbird: Breathtaing Views,Tropical Pool Paradise, Tiki Hut, Steps to Beach

Anna Maria house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$429

1 / 43

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

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$193

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

Las Palmas - 120 Park Avenue, Anna Maria

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$190

1 / 16

Home Playa- 712 North Shore Dr, Anna Maria

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$114

1 / 22

Pelican Roost 505

Anna Maria house

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$464

1 / 33

Palm Court Villas- 210 B Magnolia Ave, Anna Maria

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$145

1 / 26

Anna Cabana B: North End Pool Home just a short walk from the beach!

Anna Maria bungalow

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$129

1 / 24

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

$193

1 / 37

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

$243

1 / 35

Seabatical- 225 Willow Ave, Anna Maria

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$200

1 / 26

Fun In The Sun- 304 Gulf Blvd, Anna Maria

Anna Maria house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$243

1 / 26

Cast Villa 4

Anna Maria villa

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 54 minutes

Price per night from

$129

1 / 37

Sand Dollar- 208 76th St, Holmes Beach

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$93

1 / 28

Herons Watch- 766 North Shore Dr, Anna Maria

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$108

1 / 17
Viewing 38 of 3,121

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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