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Cottages Anna Maria Island

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63 cottages

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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

“Perfect Beach House” We loved the quaint little duplex. The house was clean and ready for us when we arrived. Tim was a dream to work with. The A/C one of the units went out while we were there, and he had someone there first thing to take care of it. We will definitely be looking to rent from Tim again in the future.

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$165

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

Bradenton Beach cottage

4 bedrooms / 4 bathrooms / sleeps 15

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$330

AMI Tree House

Bradenton Beach cottage

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 23 minutes

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$178

Anna Maria The Pink Flamingo

Holmes Beach cottage

2 bedrooms / 2 bathrooms / sleeps 6

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$241

Anthony Beach Cottages Bare Feet Retreat

Holmes Beach cottage

3 bedrooms / 1 bathroom / sleeps 6

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$259

Brand New Renovation Sea Waves Cottage

Anna Maria cottage

3 bedrooms / 2 bathrooms / sleeps 6

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$494

Newly renovation bay side cottage: Sea Breeze

Anna Maria cottage

2 bedrooms / 2 bathrooms / sleeps 4

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$345

THE SEASHELL 109 36TH ST

Holmes Beach cottage

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 12 minutes

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Price per night from

$255

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

$375

Songbird Cottage

Anna Maria Island cottage

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 16 minutes

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$148

Beach Dreams "Tangerine Dreams Villa "

Bradenton Beach cottage

1 bedroom / 1 bathroom / sleeps 3

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$346

Beach Dreams -"Dream Away Villa"

Anna Maria Island cottage

1 bedroom / 1 bathroom / sleeps 3

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Price per night from

$340

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

Bradenton Beach cottage

2 bedrooms / 1 bathroom / sleeps 4

“Lovely cottage with great location” Our time at Sea Stories was memorable. We enjoyed the location for the beach and the restaurants. The cottage was adorable with everything we needed. Wendy was so helpful in solving a problem we had with sleeping arrangements for three girls. We will come back to Anna Maria Island with Sea Stories in mind. Thank you Wendy for all your help!

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$375

Tarpon Tree House

Anna Maria cottage

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 12 minutes

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$330

Coquina Cottage A

Anna Maria cottage

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 12 minutes

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$181

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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$230

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.

Responds fast! avg. 3 hours 22 minutes

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$403

The Mermaid Cottage. Walk To Beach, Shops

Madeira Beach cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 35 minutes

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$173

The Surf Cottage. Walk to Beach, Shops & Dining

Madeira Beach cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 35 minutes

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$173

The Flamingo Cottage. Walk to Beach, Shops, Dining

Madeira Beach cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 35 minutes

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$173

The Sunshine Cottage. Walk to Beach, Shops, Dining

Madeira Beach cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 35 minutes

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$173

Starfish Cottages One Bedroom

Madeira Beach cottage

2 bedrooms / 1 bathroom / sleeps 4

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$132

March 19-26, 2022 Springbreak 3bdr on the beach Longboat key

Longboat Key cottage

3 bedrooms / 2 bathrooms / sleeps 8

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$691

CHA CHA COTTAGE 301 23RD ST

Cortez cottage

3 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 2 hours 12 minutes

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$255

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

Longboat Key cottage

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 43 minutes

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$95

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

Cortez cottage

1 bedroom / 1 bathroom / sleeps 2

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$166

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

Cortez cottage

2 bedrooms / 2 bathrooms / sleeps 5

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$197

Mar Y Sol

Cortez cottage

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 12 minutes

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$271

"Waves" Cottage on Sunset Beach

Treasure Island cottage

1 bedroom / 1 bathroom / sleeps 2

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$345

"Ocean " Cottage on Sunset Beach

Treasure Island cottage

1 bedroom / 1 bathroom / sleeps 2

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$345

Sunset Beach Cottages, 1 Bedroom Beach Cottages

Treasure Island cottage

1 bedroom / 1 bathroom / sleeps 3

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$242

Sunset Beach Cottages - 2 Bedroom Beach Cottages

Treasure Island cottage

2 bedrooms / 1 bathroom / sleeps 6

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$345

Manatee River Cottage in Historic Old Town

Palmetto cottage

3 bedrooms / 1 bathroom / sleeps 7

Responds fast! avg. 3 hours 57 minutes

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Price per night from

$121

Beach Cottage, Old-Florida Style!

Gulfport cottage

2 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$104

Perfecto's Retreat Unit #1

St. Petersburg cottage

1 bedroom / 1 bathroom / sleeps 4

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$345

John's Pass-Time Beach Front Cottage

Madeira Beach cottage

2 bedrooms / 1 bathroom / sleeps 4

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$288

Sunset Beach Treasure Island Caddy Cottage Wi-Fi Parking 119

St. Pete Beach cottage

1 bedroom / 1 bathroom / sleeps 2

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$287

Casablanca 1/1 St Pete Beach Don Cesar Zamora C

Tierra Verde cottage

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$136

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cottages in Anna Maria Island

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