Vacation Rentals & Beach Rentals in Anna Maria

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525 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

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

Anna Maria house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$747

Sea Waves in Anna Maria Island with Private Dock

Anna Maria cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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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

"Island Oasis" A single family North end canal home with pool

Anna Maria house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$748

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

Going Coastal

Anna Maria house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$311

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Price per night from

$794

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

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,156

Serendipity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,265

Simpatico

Anna Maria house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$418

C View

Anna Maria house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$394

Manatee Lookout

Anna Maria house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$332

Tripletail

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,725

Manatee Retreat

Anna Maria house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$373

Mintfish

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,150

SeaTurtle Escape

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$914

Bimini Cove

Anna Maria house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

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Price per night from

$62

Manatee Retreat Unit B

Anna Maria house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$257

Cloud 9

Anna Maria house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$1,955

Manatee Retreat Unit A

Anna Maria house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$257

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

BEACH FRONT CONDO *** MADEIRA BEACH

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$369

Beautiful Island on Boca Ciega Bay & The Beach

St. Petersburg condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$115

3 Bed/2 Bath Handicap Madeira Beach Gulf side Condo w/ Heated pool and Spa

Madeira Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$345

Treasure Island Beach Condo

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 45 minutes

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Price per night from

$156

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

Boca Ciega Condo, #107, St Petersburg, Florida

St. Petersburg condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$206

Perfecto's Retreat Unit #1

St. Petersburg cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$344

ZILLI VILLA

Longboat Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$489

Beach front condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$432

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

Land's End: Gulf-front Luxury, WIFI, HDTV

Treasure Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$395

John's Pass-Time Beach Front Cottage

Madeira Beach cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$288

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

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.

Match: Waterfront

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Price per night from

$374

Executive Waterfront Home

St. Petersburg house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$259

Runaway Bay - Bradenton Beach - Bay View Unit 193

Anna Maria Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Home away from home” This place is an incredible value. It's spacious and comfortable, and we felt right at home. Sarasota Bay is just steps from the back patio, and it's so lovely to sit outside and watch water--so many fish, dolphins, and birds right there. Everything was in good working order and clean upon our arrival. The beach is a quick walk across the street from the complex, and we spent a lot of time at the heated pool. We would love to rent this unit again! PERFECT LOCATION.

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Price per night from

$210

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