Cottages Anna Maria Island

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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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$246

HISTORIC WATERFRONT COTTAGES..DOCK...BEACH...Couples, Families, Reunions!

Bradenton Beach cottage

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 15

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$295

AMI Tree House

Bradenton Beach cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 7 minutes

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$241

Anna Maria The Pink Flamingo

Holmes Beach cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 41 minutes

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$459

Sea Waves in Anna Maria Island with Private Dock

Anna Maria cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$378

Newly renovation bay side cottage: Sea Breeze

Anna Maria cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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$355

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

Bradenton Beach cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$401

Songbird Cottage

Anna Maria Island cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$111

Beach Dreams "Tangerine Dreams Villa "

Bradenton Beach cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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$344

Beach Dreams -"Dream Away Villa"

Anna Maria Island cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$338

The Anchor- A two bedroom cottage minutes walking to beach.

Bradenton Beach cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$372

Cortez Gardens Cottage 15 , Renovated, Close to Beach, 3-Bed, 2 Bath 10 people

Bradenton Beach cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

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$228

Great rentals within 20 miles that match your search

Luxury Beach Cotttage

Sarasota cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Beautiful little cottage” We stayed at this lovely little cottage on Siesta Key mid-April. The cottage is very nice, with all the amenities, even a washer/dryer for extended stays. It's cozy, with high ceilings, a nice bathroom and kitchen/living room. The bed seemed a little small (only a double), but it was very comfortable. The wireless internet was not working when we were there, which was a little frustrating. There is a beautiful pool and nice garden areas. The private beach was also very nice. All of the staff and the owner were extremely pleasant and welcoming. We enjoyed our time there.

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$533

Starfish Cottages One Bedroom

Madeira Beach cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$139

March 23-March 30, 2024 Springbreak 3bdr on the beach Longboat key

Longboat Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$746

Sunset Beach Cottages - 2 Bedroom Beach Cottages

Treasure Island cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 2 hours 3 minutes

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$343

Sunset Beach Cottages, 1 Bedroom Beach Cottages

Treasure Island cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 2 hours 3 minutes

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$241

Guest House, 750 sq ft, private, with all amenities, parking and pool

St. Petersburg cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$98

Manatee River Cottage in Historic Old Town

Palmetto cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

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$148

John's Pass-Time Beach Front Cottage

Madeira Beach cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$287

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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$333

***Bermuda-esque Island Cottage! Steps to Sand!***

Longboat Key cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$134

Perfecto's Retreat Unit #1

St. Petersburg cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$343

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$97

“Charming studio in lovely quiet neighborhood with fenced in private outside area.” This studio has everything you'll need. It's located in a beautiful neighborhood, great for walking. There's a small park just down the road a couple of blocks where you can sit and watch the amazing sun sets or just enjoy watching the boats ride by. The owners are very nice and have a few fur babies of their own, so they may allow you to bring your doggie,too! Sue/Dawn......thank you!!!! I hope to return & stay again.

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$229

Beach Cottage, Old-Florida Style!

Gulfport cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$103

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$114

Steps to Beach+bikes VaCay getaway on PaG island

St. Pete Beach cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 1 hour 9 minutes

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$200

Cottage Haven-One Minute Walk To The Beach-Private Yards-Keyless Locks

Cortez cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 3 hours 20 minutes

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$214

AMI Lighthouse Cottage-One Minute Walk To The Beach-Keyless Locks

Cortez cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 20 minutes

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$161

Sunshine daydream directly on the sand! Rustic coastal decor with modern applian

Treasure Island cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$162

Private cottage on Treasure Island! Salty, sunny, beachy, arty, updated & comfor

Treasure Island cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$164

Unique, private, cozy, updated vintage cottage w/ sand in your toes from the fro

Treasure Island cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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$162

Beachfront Cottage - ON the Beach! A Break From The Usual Condo Or Hotel.

Treasure Island cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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$162

Responds fast! avg. 16 minutes

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$127

Comfortable Two Bedroom Cottage Steps To The Beach

Madeira Beach cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“We would like to come back” I stayed here last year with my wife and two kids. I'm on the page again because I'd like to come back. Can't remember his name anymore but the guy at itrip was really good to work with. The place was spotless. The neighbor were quiet and virtually out of sight. The beach is maybe 150 yards from the house. It was a good experience for my whole family. Only and I mean only negative is that the surrounding area is old and a little run down. That doesn't mean it's a bad or rough area, either. We live on the other side of Pinellas. This place was a great place for a restful vacation - no tiring travel involved, right on the beach, and cheap rates. Like I was saying at the start, we'd like to come back soon at some point.

Responds fast! avg. 3 minutes

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$142

Treasure Island Charm: Unwind in Style at Our Secluded 1-Bedroom Coastal Retreat

Treasure Island cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 minutes

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$172

Seaside Bliss: Charming 2-Bedroom Cottage in the Heart of the Historic Coney Isl

Treasure Island cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 minutes

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Price per night from

$218

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cottages in Anna Maria Island

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