Vacation Rentals & Beach Rentals in Anna Maria Island

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84 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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Price per night from

$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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Price per night from

$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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Price per night from

$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

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

White Sand Beaches- Bayfront Park

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$630

Rambo's Beach Retreat! Tradewinds Unit 14

Bradenton Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$453

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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Price per night from

$974

Cloud 9

Anna Maria house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$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

$516

Great rentals within 20 miles that match your search

Beautiful Location On Bay Side, Water View, Pool

Sarasota villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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$229

Perfecto's Retreat Unit #1

St. Petersburg cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$343

Pass-A-Grille Beach House

St. Pete Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$218

Serene Sarasota Getaway near shopping and golfing.

Fruitville villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$127

Ohana

Sarasota condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$144

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

$315

Alice's Beach Bungalows Private Oasis #2

Treasure Island bungalow

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$228

River Strand Luxury Condo-Tennis & Golf Community

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$86

Island Beach cottage rental w/king+2bikes+smartTV

St. Pete Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 9 minutes

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Price per night from

$224

Sunny PaG Island rental w/bikes-just steps2beach

St. Pete Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 1 hour 9 minutes

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Price per night from

$181

NW Bradenton Exectitive Home

Bradenton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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$492

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$229

Newly Remodeled Spacious Loft in Sarasota!

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$295

Stay near the beach and downtown

Sarasota house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$69

Family friendly condo on the beach - Ocean Sands

Madeira Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$158

The Sand Dollar: Historic Charm Meets Beach Chic in the Waterfront District

Gulfport apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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Price per night from

$126

Beach Cottage, Old-Florida Style!

Gulfport cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$103

Harbor Mist: Fresh & Friendly in Marina District + Private Outdoor Oasis

Gulfport house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$149

Siesta Key- Beach Chic Retreat, Siesta Key 3 Bedroom 2 Bath Apartment

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

“This was the definition of home away from home” great value for your money...very cozy, with lots of new upgrades. Easy access to the beach and restaurants.

Responds fast! avg. 1 hour 14 minutes

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Price per night from

$315

EIKO BEACHFRONT HOME 4BR/3BA**HEATED POOL&SPA*PETS OK

Treasure Island house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 13

“Water, water everywhere” So very, very close to the beach. Very helpful agent. Had 11 people with plenty of room .awesome time.

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Price per night from

$773

Sunny Sandy Escape! Steps 2 Famous Beach w/2 Bikes

St. Pete Beach cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 9 minutes

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Price per night from

$340

A Paradise for Golfers and Tennis players

Bradenton apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 27 minutes

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Price per night from

$139

BAY VIEW. SUNSETS. CLOSE TO ANNA MARIA ISLAND AND IMG ACADEMY

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$367

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rentals in Anna Maria Island

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