Vacation Rentals & Beach Rentals in Anna Maria Island

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249 beach rentals

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

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Tennis in town Pets allowed

All filters match

Price per night from

$630

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.

Match: Tennis in town Pets allowed

All filters match

Price per night from

$630

Match: Tennis in town Pets allowed

All filters match

Price per night from

$229

Serendipity Deux- Beachfront 4 Bed/heated pool/elevator

Anna Maria house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Match: Tennis in town Pets allowed

All filters match

Price per night from

$2,290

35 Steps to the Sea at Runaway Bay 112

Bradenton Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Tennis in town Pets allowed

All filters match

Price per night from

$124

Summer Breeze

Holmes Beach house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Tennis in town Pets allowed

All filters match

Price per night from

$371

Serendipity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Tennis in town Pets allowed

All filters match

Price per night from

$1,260

35 Steps to the Beach at Runaway Bay 104

Bradenton Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Tennis in town Pets allowed

All filters match

Price per night from

$124

Last Mango

Holmes Beach condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Tennis in town Pets allowed

All filters match

Price per night from

$202

Coca Cabana

Holmes Beach condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Tennis in town Pets allowed

All filters match

Price per night from

$344

Waves on Anna Maria

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Tennis in town Pets allowed

All filters match

Price per night from

$974

Cloud 9

Anna Maria house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 8

Match: Tennis in town Pets allowed

All filters match

Price per night from

$1,949

Anna Maria Beach House

Anna Maria house

  • 5 bedrooms
  • 7 bathrooms
  • sleeps 8

Match: Tennis in town Pets allowed

All filters match

Price per night from

$662

Rum Dog

Holmes Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Tennis in town Pets allowed

All filters match

Price per night from

$173

Compass Rose

Anna Maria house

  • 9 bedrooms
  • 9 bathrooms
  • sleeps 8

Match: Tennis in town Pets allowed

All filters match

Price per night from

$1,060

Winding Waves

Anna Maria house

  • 9 bedrooms
  • 9 bathrooms
  • sleeps 8

Match: Tennis in town Pets allowed

All filters match

Price per night from

$1,060

Portside Paradise

Holmes Beach house

  • 4 bedrooms
  • 7 bathrooms
  • sleeps 8

Match: Tennis in town Pets allowed

All filters match

Price per night from

$523

Miracle's Runaway Bay 117

Bradenton Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Tennis in town Pets allowed

All filters match

Price per night from

$124

Manatee Lookout

Anna Maria house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Tennis in town Pets allowed

All filters match

Price per night from

$330

Island Dream

Holmes Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Tennis in town Pets allowed

All filters match

Price per night from

$273

Sunset Seacret

Holmes Beach condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Tennis in town Pets allowed

All filters match

Price per night from

$202

Tripletail

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Tennis in town Pets allowed

All filters match

Price per night from

$1,719

Mintfish

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Tennis in town Pets allowed

All filters match

Price per night from

$1,146

On The Rocks

Bradenton Beach house

  • 8 bedrooms
  • 9 bathrooms
  • sleeps 18

Match: Tennis in town Pets allowed

All filters match

Price per night from

$953

Paradise Beach

Bradenton Beach house

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 18

Match: Tennis in town Pets allowed

All filters match

Price per night from

$1,260

Surfer's Dream

Holmes Beach house

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 8

Match: Tennis in town Pets allowed

All filters match

Price per night from

$636

Swanky Bubbles

Holmes Beach house

  • 9 bedrooms
  • 9 bathrooms
  • sleeps 18

Match: Tennis in town Pets allowed

All filters match

Price per night from

$916

Beautiful Longboat Key Home!

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 27 minutes

Match: Tennis in town Pets allowed

All filters match

Price per night from

$514

From Dusk 'Til Dune

Anna Maria house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 8

Match: Tennis in town Pets allowed

All filters match

Price per night from

$742

These homes match some but not all of your filters. Clear all filters

Kai Blue

Holmes Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Pets allowed, Tennis in town

1 of 2 filters match

Price per night from

$457

Coastal Serenity

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Pets allowed, Tennis in town

1 of 2 filters match

Price per night from

$674

Penthouse in Paradise

Holmes Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Pets allowed, Tennis in town

1 of 2 filters match

Price per night from

$181

Luum at the Shore

Holmes Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Tennis in town

1 of 2 filters match

Price per night from

$572

Bodacious Oasis

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Pets allowed, Tennis in town

1 of 2 filters match

Price per night from

$417

Holmes Sweet Holmes

Holmes Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Tennis in town

1 of 2 filters match

Price per night from

$227

Come Sail A Bay

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Tennis in town

1 of 2 filters match

Price per night from

$264

Bean Point Unit B

Anna Maria villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Tennis in town

1 of 2 filters match

Price per night from

$260

Grand Island Oasis

Bradenton Beach house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 18

1 of 2 match: Pets allowed, Tennis in town

1 of 2 filters match

Price per night from

$911

Viewing 38 of 249
rentals in Anna Maria Island

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