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Cottages Siesta Key

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52 cottages

Beach Place Cottages - Seahorse Cottage - Peak of the Gulf - Beach Access #11

Siesta Key cottage

1 bedroom / 1 bathroom / sleeps 4

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$206

Walk to Beach, Beautifully Renovated with Highend Finishings, Wifi/Cable, Heated

Siesta Key cottage

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 minutes

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$163

Siesta Key Beach Cottages on Crescent

Siesta Key cottage

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 30 minutes

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$267

Siesta Key 'Casa Serena' w/Private Pool + Lanai!

Siesta Key cottage

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 28 minutes

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$219

Lush Siesta Key Cottage - 4 Blocks to Main St!

Siesta Key cottage

2 bedrooms / 2 bathrooms / sleeps 3

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$66

Siesta Beach Place-Starfish Cottage, Steps to the Sand, View of Pool, Access #11

Siesta Key cottage

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$196

NEW! Bright Sarasota Bungalow 5 Mi to Siesta Beach

Siesta Key cottage

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 28 minutes

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Price per night from

$128

Great rentals within 20 miles that match your search

Anthony Beach Cottages Bare Feet Retreat

Holmes Beach cottage

3 bedrooms / 1 bathroom / sleeps 6

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$258

The Urban Cottage A Romantic Getaway!

Sarasota cottage

1 bedroom / 1 bathroom / sleeps 3

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Price per night from

$150

Charming cottage, gateway into world famous siesta key beaches

Sarasota cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 18 minutes

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Price per night from

$127

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

Longboat Key cottage

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$689

Cottage on walking Distance To Casey Key Beach

Nokomis cottage

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$92

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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$120

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

Bradenton Beach cottage

4 bedrooms / 4 bathrooms / sleeps 15

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$149

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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Price per night from

$335

Longboat Key Club

Longboat Key cottage

2 bedrooms / 2 bathrooms / sleeps 4

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$135

Bay View Cottage

Sarasota cottage

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$212

" Fish Tales"- 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

$189

Songbird Cottage

Anna Maria Island cottage

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 1 hour 51 minutes

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Price per night from

$102

Anna Maria The Pink Flamingo

Holmes Beach cottage

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 5 minutes

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Price per night from

$206

CHA CHA COTTAGE 301 23RD ST

Cortez cottage

3 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 3 hours 10 minutes

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Price per night from

$212

2404 AVE B

Cortez cottage

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 10 minutes

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Price per night from

$231

103 36th ST

Holmes Beach cottage

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 21 minutes

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Price per night from

$436

MIM'S COTTAGE BY THE C

Cortez cottage

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 21 minutes

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Price per night from

$403

THE SEASHELL 109 36TH ST

Holmes Beach cottage

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 21 minutes

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Price per night from

$250

110 31ST ST

Holmes Beach cottage

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 21 minutes

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$326

"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!

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$326

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!

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$206

On the Beach Paradise u

Holmes Beach cottage

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$206

3003 AVE F- EAST

Holmes Beach cottage

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 21 minutes

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Price per night from

$308

Beach Dreams -"Dream Away Villa"

Anna Maria Island cottage

1 bedroom / 1 bathroom / sleeps 3

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Price per night from

$326

South Venice Cottage

South Venice cottage

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$132

NEW! Sun n Fun Resort Home w/Community Amenities

Fruitville cottage

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$54

NEW! Anna Maria Island Retreat: Walk to the Gulf!

Cortez cottage

3 bedrooms / 2 bathrooms / sleeps 6

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$194

NEW! Canalfront House w/ Pool in San Remo Shores!

Bradenton Beach cottage

4 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 3 hours 28 minutes

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Price per night from

$213

NEW! Vibrant & Pet-Friendly Oasis w/ Resort Perks!

Fruitville cottage

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 28 minutes

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Price per night from

$71

Sarasota Bungalow w/ Pergola, Garden & Waterfalls!

Sarasota cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 28 minutes

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Price per night from

$119

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. 2 hours 38 minutes

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Price per night from

$200

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cottages in Siesta Key

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