Vacation Rentals & Beach Rentals in Anna Maria

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92 beach rentals

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

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$633

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.

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Price per night from

$633

Jacaranda Artist Retreat

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$219

Serendipity Deux- Beachfront 4 Bed/heated pool/elevator

Anna Maria house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$2,300

Tripletail

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,725

Serendipity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,265

Mintfish

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,150

White Sand Beaches- Bayfront Park

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$633

Waves on Anna Maria

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$978

Cloud 9

Anna Maria house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$1,955

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Sea Waves in Anna Maria Island with Private Dock

Anna Maria cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Pets allowed, Fishing

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Price per night from

$379

Newly renovation bay side cottage: Sea Breeze

Anna Maria cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$356

Enjoy our Beach, Pool and Dock! 100 5-Star Reviews!

Anna Maria house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Pets allowed, Fishing

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Price per night from

$747

From Dusk 'Til Dune

Anna Maria house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 8

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Price per night from

$745

Anna Maria Beach Serenity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 20 minutes

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Price per night from

$1,149

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Price per night from

$794

Modern home with Private pool, walk to the beach, Putting green & Ping pong

Anna Maria house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$914

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Price per night from

$1,035

Winding Waves

Anna Maria house

  • 9 bedrooms
  • 9 bathrooms
  • sleeps 8

1 of 2 match: Fishing, Pets allowed

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Price per night from

$1,064

Manatee Lookout

Anna Maria house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$330

Experience the luxury of private beach living with TWO heated pools!

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Fishing, Pets allowed

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Price per night from

$1,156

Beach Bliss

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Fishing, Pets allowed

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Price per night from

$1,150

FantaSea

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,495

Great rentals within 20 miles that match your search

Fine Waterfront Living . Steps to Beach

St. Pete Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$489

SUNSHINE HOLIDAY

St. Petersburg manor house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

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Price per night from

$1,150

Beautiful Sunkst Cottage Bradenton Beach - AMI-Tropical Setting - Heated Pool

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$518

SPECIAL! $650 8/24 - 8/31. PRIME LOCATION AMI DIRECTLY ON BEACH HEATED POOL

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$288

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

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Price per night from

$1,003

Alice's Beach Bungalows Private Oasis TI, FL

Treasure Island bungalow

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Short vacation” Still on our short vacation. So far everything is perfect! Susan has been very helpful with any questions and has been there anytime we had needed her. Hot tub is great! Place is super clean and efficient.

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Price per night from

$218

Modern Studio, Designer Kitchen Walkable Downtown

St. Petersburg apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$133

Pass-A-Grille Beach House

St. Pete Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$219

Alice's Beach Bungalows 2 bedroom

Treasure Island house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“A perfect spot for us and for our golden retriever!” What a great place to enjoy the beauty of Treasure Island. The bungalow that we stayed in was wonderful...clean, a well stocked kitchen, beach towels, a great backyard. Susan, the owner, was also great to work with on every level. She was attentive, often checking in on us to make sure all was going great with our stay. She was also responsive to our rental needs and responded immediately if we had a question, etc.. She also embraced our golden retriever and he, too, immediately became fast friends with Susan. This bungalow is literally a block from the beach, a short walk over the bridge to John's Pass and close to grocery shopping, lots of great restaurants right on the beach, etc.. A great experience and we will definitely plan to stay at this bungalow again!

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Price per night from

$317

Alice's Beach Bungalows Private Oasis #2

Treasure Island bungalow

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$229

Light and Airy and Private, Great Location

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$230

X Alice's Beach Bungalows 2 bdrm 500' to Beach!

Treasure Island house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“Loved it” Quiet but close to what ever you want. The beach is just across the road, one restaurant within walking distance, the main road to mainland is 1.2 miles away, but everything you need is on Gulf Blvd. The house and yard were well maintained. Inside was excellent shape with open floor plan that gave a sense of a large space. The kitchen was open and had about everything you would need including basic supplies like coffee, sugar, some spices, etc. We had arrived 1/2 hr early and cleaning lady was there so we went across the bridge to Johns Pass about a 1/4 mi and had a drink and came back as she was leaving to get a new microwave as it had broken when she checked it. There is a large back yard and private sitting area. The hot tub is in backyard along with a grill. The bedrooms were large with plenty of closet space. The bath room was roomy with a " sunken tub" that consisted of one step down for a seat and another step to the bottom for about 6-8 inches of water. However the shower was more that adequate. A really nice, comfortable place to stay for a few days.

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Price per night from

$374

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$230

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Price per night from

$107

Downtown Sarasota Historic Burns Court Adorable Bungalow

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$296

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