Vacation Rentals & Beach Rentals in Anna Maria

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3,245 beach rentals

(38) Excellent 

123

Ocean View 3 bedroom, pool, North Shore Drive

Anna Maria Island / Anna Maria

Anna Maria house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“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
…see more

Price per night from

$207

Responds fast!
avg. 49 minutes

Price per night from

$207

(4) Excellent 

22

BEACHFRONT HOME, PRIVATE BEACH, DOGS STAY FREE, GREAT VIEWS, WALKING BEACH

Anna Maria Island / Anna Maria

Anna Maria house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$228

Responds fast!
avg. 2 hours 38 minutes

Price per night from

$228

43

Yellowbird

Anna Maria Island / Anna Maria

Anna Maria house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$429

Price per night from

$429

29

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

Anna Maria Island / Anna Maria

Anna Maria house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$168

Price per night from

$168

31

742 Jacaranda Rd

Anna Maria Island / Anna Maria

Anna Maria house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly

Price per night from

$213

Price per night from

$213

24

Villa Palma

Anna Maria Island / Anna Maria

Anna Maria house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Ask about children
  • Air conditioning

Price per night from

$171

Price per night from

$171

(1) Excellent 

23

Bean Point Beach Cottage

Anna Maria Island / Anna Maria

Anna Maria cottage

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Ask about children
  • Air conditioning

Price per night from

$257

Price per night from

$257

(3) Excellent 

23

Beach Walk

Anna Maria Island / Anna Maria

Anna Maria house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Ask about children
  • Air conditioning

Price per night from

$186

Price per night from

$186

(2) Excellent 

39

Dolphin Pointe

Anna Maria Island / Anna Maria

Anna Maria house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$277

Responds fast!
avg. 1 hour 9 minutes

Price per night from

$277

(4) Excellent 

23

Sea Oats

Anna Maria Island / Anna Maria

Anna Maria house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Ask about children
  • Air conditioning

Price per night from

$186

Price per night from

$186

(12) Excellent 

23

Mangoes on Magnolia

Anna Maria Island / Anna Maria

Anna Maria house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children
  • Air conditioning
“Paradise Found” Fabulous location on the beautiful north end of Anna Maria Island. Lovely days starting with a walk to the Gulf. Back to Ginny and Jane E's for brunch. A swim in the pool followed by relaxing in the spa. A walk to a nearby restaurant f
…see more

Price per night from

$189

Price per night from

$189

(6) Excellent 

23

A Place in Paradise A

Anna Maria Island / Anna Maria

Anna Maria house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Ask about children
  • Air conditioning

Price per night from

$121

Price per night from

$121

34

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

Anna Maria Island / Anna Maria

Anna Maria house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$187

Price per night from

$187

(2) Very Good 

23

Casa Palma

Anna Maria Island / Anna Maria

Anna Maria house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children
  • Air conditioning

Price per night from

$171

Price per night from

$171

(9) Very Good 

32

744 Jacaranda Rd

Anna Maria Island / Anna Maria

Anna Maria house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
“Nice getaway” Nice home! Large enough for family. Decks and heated pool were great!
…see more

Price per night from

$315

Price per night from

$315

(12) Excellent 

23

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

Anna Maria Island / Anna Maria

Anna Maria house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“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.
…see more

Price per night from

$409

Responds fast!
avg. 1 hour 33 minutes

Price per night from

$409

35

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

Anna Maria Island / Anna Maria

Anna Maria house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$303

Price per night from

$303

29

The Lime Door

Anna Maria Island / Anna Maria

Anna Maria house

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Nearest beach 0.5 mi
  • Child Friendly
  • Air conditioning

Price per night from

$279

Price per night from

$279

(10) Very Good 

24

GOOD FRIEND

Anna Maria Island / Anna Maria

Anna Maria house

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Ask about children
  • Air conditioning
“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
…see more

Price per night from

$220

Price per night from

$220

(1) Excellent 

24

116 Maple Breeze

Anna Maria Island / Anna Maria

Anna Maria house

4 7 7 nights min

  • 4 bedrooms
  • sleeps 7
  • 7 nights min
  • Child Friendly

Price per night from

$263

Price per night from

$263

(33) Very Good 

Certificate of Excellence

46

Gorgeous views,spectacular home!

Anna Maria Island / Anna Maria

Anna Maria house

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“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.
…see more

Certificate of Excellence

Price per night from

$408

Responds fast!
avg. 2 hours 25 minutes

Price per night from

$408

23

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

Anna Maria Island / Anna Maria

Anna Maria house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$211

Price per night from

$211

30

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

Anna Maria Island / Anna Maria

Anna Maria house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$170

Price per night from

$170

(2) Very Good 

24

Little Slice of Paradise

Anna Maria Island / Anna Maria

Anna Maria apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Ask about children
  • Air conditioning

Price per night from

$100

Price per night from

$100

19

Beautiful luxury beach front condominium

Anna Maria Island / Anna Maria

Anna Maria condo

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$722

Price per night from

$722

22

Seas The Day

Anna Maria Island / Anna Maria

Anna Maria house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$171

Price per night from

$171

(6) Excellent 

23

Blue Heron Waterfront House Anna Maria island

Anna Maria Island / Anna Maria

Anna Maria house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$285

Responds fast!
avg. 2 hours 8 minutes

Price per night from

$285

41

5 O'Clock Somewhere

Anna Maria Island / Anna Maria

Anna Maria house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$286

Price per night from

$286

(1) Excellent 

33

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

Anna Maria Island / Anna Maria

Anna Maria house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$154

Price per night from

$154

33

Pelican Roost 505

Anna Maria Island / Anna Maria

Anna Maria house

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child Friendly

Price per night from

$532

Price per night from

$532

(4) Excellent 

23

19 Palms. Quaint Old-Florida Charm

Anna Maria Island / Anna Maria

Anna Maria house

2 6 4 nights min

  • 2 bedrooms
  • sleeps 6
  • 4 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$201

Responds fast!
avg. 2 hours 35 minutes

Price per night from

$201

(12) Excellent 

22

Starfish Dreams

Anna Maria Island / Anna Maria

Anna Maria house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Ask about children
  • Air conditioning
“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
…see more

Price per night from

$214

Price per night from

$214

(1) Excellent 

24

Absolutely Anna

Anna Maria Island / Anna Maria

Anna Maria house

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Ask about children
  • Air conditioning

Price per night from

$250

Price per night from

$250

(2) Excellent 

21

Anna Maria Island "High End" Vacation Rental

Anna Maria Island / Anna Maria

Anna Maria house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Excellent” Beautiful place, secluded and private. Very clean and Pet friendly. Could not ask for anything more.
…see more

Price per night from

$287

Responds fast!
avg. 3 hours 12 minutes

Price per night from

$287

(1) Excellent 

24

Tequila Sunset

Anna Maria Island / Anna Maria

Anna Maria house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$157

Price per night from

$157

23

Sea Haze Cottage - Gorgeous waterfront pool beachhouse

Anna Maria Island / Anna Maria

Anna Maria house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly

Price per night from

$344

Price per night from

$344

19

Salt Box Cottage

Anna Maria Island / Anna Maria

Anna Maria cottage

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Ask about children
  • Air conditioning

Price per night from

$140

Price per night from

$140

(5) Excellent 

24

Villa Marianne

Anna Maria Island / Anna Maria

Anna Maria house

5 8 min stay varies

  • 5 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children
  • Air conditioning

Price per night from

$300

Price per night from

$300

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.