Vacation Rentals & Beach Rentals in Anna Maria Island

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259 beach rentals

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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$209

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

$744

A Pearl of a Beach Home - now with luxury Saltwater heated pool and hot tub

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Perfect Luxury” Our 5-week stay at this vacation rental was absolutely perfect. The house was everything you could ask for and more. We have stayed in many vacation rentals in the last 20 or so years that we have been coming to anna Maria Island and I have to say this one was right at the top of the list. The kitchen was outfitted with everything you could want. The beds were very comfortable. The neighborhood was nice and quiet. Short walk to the beach. The owners were very nice to deal with and always responded quickly and were very warm and helpful. Definitely can recommend this vacation rental.

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$476

Songbird Cottage

Anna Maria Island cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$110

SAPPHIRE - HARBOR ISLE

Bradenton Beach townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$287

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

$2,290

Serendipity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,260

White Sand Beaches- Bayfront Park

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$631

Rambo's Beach Retreat! Tradewinds Unit 14

Bradenton Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$454

Tripletail

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,718

Mintfish

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,145

Waves on Anna Maria

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$974

Cloud 9

Anna Maria house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 8

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$1,947

Beautiful Longboat Key Home!

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 27 minutes

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Price per night from

$517

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Anna Maria Island Sunshine Kiss Villa

Holmes Beach studio

  • Studio
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

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Price per night from

$150

203 PERIWINKLE - PRETTY PALMS

Anna Maria house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$553

A Gulf Front Paradise ! Newly updated , wide open wall to wall view, spacious cl

Bradenton Beach condo

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 16 minutes

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Price per night from

$458

Gulf Beach Unit 03 on Beach side, gorgeous interior, miles of beach, Anna Maria

Holmes Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$401

Walk to the beach, from this remodeled condo! Pool, WIFI, restaurants, shopping

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 16 minutes

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Price per night from

$139

Responds fast! avg. 16 minutes

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Price per night from

$232

Beachfront view, toes in the sand and gulf. Simply paradise, book now your beach

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 16 minutes

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Price per night from

$275

Updated w/bay view , across from the beach , pool, elevator , close restaurants

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 16 minutes

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Price per night from

$174

If this isn't your view, you need to change your latitude ! Toes in the sand bea

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 16 minutes

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Price per night from

$275

Misty Beach

Holmes Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$186

Pelican Cove 16

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$229

Flip Flops Forever

Holmes Beach house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$419

House of the Sea

Holmes Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$251

Starfish Oceanside

Bradenton Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$113

Newly renovation bay side cottage: Sea Breeze

Anna Maria cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$354

The Cannon- A two bedroom adorable cottage minutes walking to beach

Bradenton Beach cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$401

Beach Dreams -"Dream Away Villa"

Anna Maria Island cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$338

Piece of Paradise on Beautiful Anna Maria Island VRC 20-000087

Holmes Beach villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$148

2-Unit Beach to Bay Cottage...NOT Grandma's place!...100 feet to beach!

Bradenton Beach cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Best home away from home at the beach.” I spent a lot of time searching for a bungalow at the beach and my expectations were surpassed when I opened the door! The owners were thoughtful in design, layout and furnishings to provide a laid back experience at the beach. I wished I could have stayed forever - it was that nice. I especially enjoyed the fully stocked kitchen which included colorful dishes to match the colorful walls and great blue floor! Best of all - location - you can walk everywhere as you are right in the historic Bridge Street neighborhood.

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Price per night from

$245

BAY FRONT HOUSE WITH PRIVATE DOCK

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 31 minutes

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Price per night from

$344

Castnetter Beach Resort 2

Bradenton Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$315

Steps to the Beach

Holmes Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$164

Cortez Gardens Cottage 11, Renovated and close to Beach, 3-Bed, 2-Bath 10

Bradenton Beach apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$228

AMI Tree House

Bradenton Beach cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 7 minutes

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Price per night from

$241

Viewing 38 of 259
rentals in Anna Maria Island

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