Houses Osprey

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71 houses

Peaceful Home, close to siesta key and DT Sarasota

Fruitville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 13

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Price per night from

$338

Super Cute Cottage--Private--Walk/Bike to Beach

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$258

New York Avenue Rancher

Gulf Gate Estates house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$444

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Siesta Key Beach : 2 Bedroom, 3 Beds, 3 Bathroom Duplex & Heated Pool

Siesta Key apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$205

Just Minutes from the White Sandy Siesta Beach

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“It was very cozy and comfortable apartment!” We loved to spend our vacation at this place. Really close to the beach, to different restaurants, and all kind of stores.

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Price per night from

$115

*** SUPER SPECIAL RATES at Harbor Towers ***

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 38 minutes

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Price per night from

$114

Gulfview/Bayfront Condo with Million Dollar Views on Siesta Key

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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$109

A Wonderful Pool House on a lake full of wildlife.

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Location location” Great house convincent , clean , close to everything

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$121

Beach house for rent in siesta key beach.

Siesta Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

Responds fast! avg. 2 hours 4 minutes

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Price per night from

$1,001

CKBH (Casey Key Beach House)

Osprey house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$653

Tiny House Siesta - Tiny House Amy

Siesta Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$377

Tiny House Siesta - Red Lifeguard Stand

Siesta Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$442

Oceanfront home w/sunset views of Sarasota Bay

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$628

4 minute flip flop walk to the beach! Starfish 2/2

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$338

4 Bed 3bath Water front home

Sarasota house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$435

Tiny House - Green Lifeguard Stand

Gulf Gate Branch house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$464

Tiny House - Flamingo

Gulf Gate Branch house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$398

Tiny House - Blue Lifeguard Stand

Gulf Gate Branch house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$421

Tiny House - The Siesta

Gulf Gate Branch house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$373

Tiny House - Margarita

Gulf Gate Branch house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$469

Tiny House - Seashell

Gulf Gate Branch house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$314

Hidden gem close to everything

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 13 minutes

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Price per night from

$217

Oceanfront home

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$685

The Suite Retreat Room at The Breathing Space Wellness House

Sarasota house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$343

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Price per night from

$572

Renovated Beach Front 2BR/2BA Condo, Steps to beach, Gulf of Mexico Views

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$277

Private Retreat on Siesta Dr

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 49 minutes

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Price per night from

$515

5 min away from the beach

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$229

Siesta Key Beach Condo, 2Br/2Ba Direct Beach Front

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“What a great view” We usually rent a house one block from the main Siesta Key beach area. This year friends rented the house and my husband and I stayed in this condo for a week. Loved the view of the beach from the living room! Loved the lani! Location was great. Pool was massive compared to our usual house pool, however we did have to walk thru parking lot to get there. The noise from the hall was annoying. And I did miss my temperpedic mattress, but had a great relaxing time.

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Price per night from

$327

The Hideaway: 4/2 W Heated Pool and Outdoor Spaces, 10 mins to Sarasota Beach

Gulf Gate Estates house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$372

Coastal Cottage

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$172

Flamingo Cottage

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$172

Sea Shell Cottage

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$172

Tropical Breeze Triple Cottages, Sleeps 16

Sarasota house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 16

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Price per night from

$681

Sea Glass Dual Cottages, Sleeps 12, Heated Pool

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$401

Dream beach, pool/spa retreat!

Siesta Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

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Price per night from

$343

BeautifulHome with Pool - 3 miles from Siesta Key Beach

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 38 minutes

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Price per night from

$241

SIestaKeyBNB

Gulf Gate Estates house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

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Price per night from

$241

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