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Cottages Anna Maria Island

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88 cottages

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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$126

On the Beach Paradise d

Holmes Beach cottage

2 bedrooms / 1 bathroom / sleeps 6

“Absolutely beautiful!” Everything was perfect. Enjoyed coffee on the beach every morning and beautiful sunsets every evening. Can't wait to go back next year!

Responds fast! avg. 3 hours 5 minutes

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$207

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

Bradenton Beach cottage

4 bedrooms / 4 bathrooms / sleeps 15

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$156

PLAYA ESMERALDA/INNATTHBEACH SUITES #3 BY BRIDGE STREET

Bradenton Beach cottage

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 26 minutes

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$137

New 'Searenity' Stand alone cottage 45 second walk to beach & bay dock pole incl

Bradenton Beach cottage

2 bedrooms / 1 bathroom / sleeps 4

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$206

The Tree House

Bradenton Beach cottage

2 bedrooms / 2 bathrooms / sleeps 6

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$123

Anna Maria The Pink Flamingo

Holmes Beach cottage

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 10 minutes

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$239

Brand New Renovation Sea Waves Cottage

Anna Maria cottage

3 bedrooms / 2 bathrooms / sleeps 6

Travelers’ Choice award

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$217

Newly renovation bay side cottage: Sea Breeze

Anna Maria cottage

2 bedrooms / 2 bathrooms / sleeps 4

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$217

On the Beach Paradise u

Holmes Beach cottage

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 13 minutes

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$222

Gertie's East - a great 1/1, just steps to the beach. With Relaxing Pool!

Holmes Beach cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 32 minutes

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$110

PLAYA ESMERALDA/INNATTHEBEACH SUITES #2 BY BRIDE STREET

Bradenton Beach cottage

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 26 minutes

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$134

PLAYA ESMERALDA/INNATTHEBEACH SUITES #5 BY BRIDGE STREET

Bradenton Beach cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 26 minutes

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$124

PLAYA ESMERALDA/INNATTHEBEACH SUITES #4A BY BRIDGE STREET

Bradenton Beach cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 26 minutes

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$121

PLAYA ESMERALDA/INNATTHEBEACH SUITES #4 BY BRIDGE STREET

Bradenton Beach cottage

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 26 minutes

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$133

PLAYA ESMERALDA / INNATTHEBEACH SUITES # 1

Bradenton Beach cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 26 minutes

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$112

Las Brisas, Cottage on bay side of Island.

Bradenton Beach cottage

2 bedrooms / 2 bathrooms / sleeps 7

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$211

" Fish Tales"- A two bedroom adorable cottage minutes walking to beach

Bradenton Beach cottage

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 3 hours 48 minutes

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$190

Songbird Cottage

Anna Maria Island cottage

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 1 hour 9 minutes

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$91

Beach Dreams "Tangerine Dreams Villa "

Bradenton Beach cottage

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 3 hours 48 minutes

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$230

Beach Dreams -"Dream Away Villa"

Anna Maria Island cottage

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 3 hours 48 minutes

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$190

"Sea Story" 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!

Responds fast! avg. 3 hours 48 minutes

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$194

SHORE LEAVE PRIVATE COTTAGE

Holmes Beach cottage

1 bedroom / 1 bathroom / sleeps 5

Responds fast! avg. 1 hour 20 minutes

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$76

Great rentals within 20 miles that match your search

The Sunshine Cottage. Walk to Beach, Shops, Dining

Madeira Beach cottage

1 bedroom / 1 bathroom / sleeps 2

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$185

The Urban Cottage A Romantic Getaway!

Sarasota cottage

1 bedroom / 1 bathroom / sleeps 3

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$125

Charming cottage, gateway into world famous siesta key beaches

Sarasota cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 21 minutes

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$93

The Flamingo Cottage. Walk to Beach, Shops, Dining

Madeira Beach cottage

1 bedroom / 1 bathroom / sleeps 2

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$185

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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$457

March 21-28, 2020 Springbreak 3bdr on the beach Longboat key

Longboat Key cottage

3 bedrooms / 2 bathrooms / sleeps 8

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$739

Braden River Bayou Cottage

Lakewood Ranch cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 10 minutes

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$136

Guest Cottage, clean, convenient and remodeled.

Sarasota cottage

/ 1 bathroom / sleeps 2

“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.

Responds fast! avg. 43 minutes

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$142

Just 100 Steps Away from the White Sand of the World Renowned Siesta Beach

Sarasota cottage

2 bedrooms / 2 bathrooms / sleeps 6

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$325

Cottage on Treasure Island in the Gulf of Mexico

Treasure Island cottage

1 bedroom / 1 bathroom / sleeps 4

“very efficient” every thing within distance very nice beach, lots of find restaurants, Great fishing, Nightlife entertainment excellent public transportation taxi cab service very good

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$96

Wyatt Beach House

Treasure Island cottage

2 bedrooms / 2 bathrooms / sleeps 5

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$226

Perfecto's Retreat Unit #1

St. Petersburg cottage

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 54 minutes

Travelers’ Choice award

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$138

Sea Turtle Cabana

Sarasota cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 51 minutes

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$117

Starfish Cottages One Bedroom

Madeira Beach cottage

2 bedrooms / 1 bathroom / sleeps 4

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$101

Downtown Cottage

Sarasota cottage

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$64

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