Cottages Siesta Key

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425 cottages

“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

Coral Reef Cutie 2Bedroom Bungalow - 4 Miles to Siesta Key

Osprey cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 14 minutes

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$132

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White Sands Village - Unit 112

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$125

White Sands Village - Unit 618

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$164

Harbor Towers

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$138

Charming Private Studio in Historic Downtown Area

Sarasota studio

  • Studio
  • 1 bathroom
  • sleeps 3

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$258

Blue Haven Retreat

Gulf Gate Estates house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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$213

Blue Haven B

Gulf Gate Estates house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$125

Blue Haven A

Gulf Gate Estates house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$125

Coastal Oasis

Nokomis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$228

4 Bed 3bath Water front home

Sarasota house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$436

“gracious and spacious” Lovely home and great location to walk throughout Siesta Key Village and the beautiful sands of the beach!! We were able to have everyone together for a great vacation.

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$148

Piece of Paradise

Sarasota condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 minutes

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$95

Beautiful, Affordable Close to famous Siesta Beach

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“It was wonderful!” Everything about the trip and condo was great! Mike met us to give us the keys and we called him for suggestions about restaurants, etc. and he was very helpful. The condo was very clean and had everything we needed. It was also great that we were able to use the beach chairs and umbrella. I am already trying to figure out when we can go again.

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$163

SunWay Suites Unit 3 Seagull

Sarasota apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$149

Sarasota Downtown, Best Location For Your Vacation !!!

Lido Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

Responds fast! avg. 1 hour 57 minutes

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$194

Great location, quiet, peaceful, and comfortable

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$46

5 min drive to the beach 8 min to Siesta Key

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 1 minutes

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$206

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$138

Buttonwood 442

Gulf Gate Estates condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$290

Vista Hermosa - 302C

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$172

Siesta Beach House - 203 / Sunny Daze

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$115

Siesta Surf Cottage #1

Siesta Key log cabin

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$140

Beach Road - Bari

Siesta Key studio

  • Studio
  • 1 bathroom
  • sleeps 3

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$79

Sea Club II

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$166

Blue Ranch Retreat

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$228

Beach Road - Capri

Siesta Key studio

  • Studio
  • 1 bathroom
  • sleeps 4

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$91

Siesta Surf Cottage #3

Siesta Key log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$153

Siesta Beach House - 202

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$115

Siesta Surf Cottage #2

Sarasota log cabin

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$140

Castel Del Mare 1624 - 402

Gulf Gate Estates condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$115

Stoneybrook Condo #926

Gulf Gate Estates condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$108

Siesta Beach House - 204

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$115

Siesta Beach House - 310 / Come n' Beach It

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$115

Responds fast! avg. 4 minutes

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$126

Live Like a Local in the Heart of Sarasota!

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$251

#7 Loft Apartment in Historic District Downtown Sarasota

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$305

Luxury Village Townhouse w/ Gulf and Beach Views

Siesta Key townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

“A wonderful home in an equally wonderful location.” The home provides a truly enjoyable family situation. The quality of the furnishings is very nice, the living space is very well maintained and clean and my interaction with the owner was always timely and courteous. My wife and I shared the home with our 14 year old granddaughter during our stay and the quiet enjoyment of the pool and the easy 1-2 minute walk to the Gulf of Mexico and the 5 minute walk to the heart of Siesta Key Village made the location hard to beat. Except for our day trips no car was needed. This is our second stay in the home and we will look to reserving it for our next visit. There were absolutely no disappointments only wonderful experiences.

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Price per night from

$659

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