Osprey Rentals

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18 Houses

Heated pool home near Siesta Key

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$262

2 MINUTE WALK TO SIESTA BEACH!! (really) 1 MINUTE TO POOL. GREAT VALUE!!!

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Happy Customer” We had an amazing time. The owners were so nice & made us feel so welcomed. I couldnt have been happier with our stay & we look forward to staying there again soon when life slows back down. Highly recommend this home♡

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$309

Turtle Beach - Gulf-Front Condo - 2BR - Free Boat Docks - Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$266

Beachfront Condo - 3 BR- Heated Pool - Free Boat Docks – Upscale – Siesta Key

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$311

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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Price per night from

$121

Siesta Key - Beachfront Condo - 2 BR – Free Boat Docks - Turtle Beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Romantic place. Perfect for young families with small kids” Firshermans Cove is on a shore side. The views are amazing as well as beach which is clean and not crowded at all. Easy check in/out and very quiet place, was ideal in our case, young family with 1,5 old boy. It was nice stay and we hopefully come back again.

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Price per night from

$266

Siesta Key - Gulf-Front Retreat - 2 BR – Free Boat Docks - Upscale

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Excellent location for a great vacation!” This is the fifth time we have had the pleasure of vacationing at El Galeon. We love the location with the beautiful beach access and walking to restaurants. We love the Manasota Key and have been vacationing there for the last seventeen years. El Galeon Gulf Unit 2 is our favorite place to stay with plenty of space and everything we need for a wonderful stay. We have already reserved "our place" for 2015.

Match: High chair

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Price per night from

$266

Beachfront Condo - 3 BR- Heated Pool - Free Boat Docks – Upscale – Siesta Key

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Great location!” The unit was just as described and pictures matched. The view of the ocean and bay were gorgeous. The kitchen was well equipped and there were lots of toys and chairs for the beach.

Match: High chair

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Price per night from

$311

BEACHFRONT CONDO - THREE BEDROOM - HEATED POOL - FREE BOAT DOCKS - RENOVATED

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Trip to paradise” Renting unit was very easy. Unit was the best layout was great. Amenities within we're well thought, out and for us anything we wanted was there including beach chairs. View of ocean was breath taking along with sunsets. I will come back again.

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Price per night from

$311

GULF FRONT ON #1 Beach! Siesta Dunes (by owner)

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Perfect, Perfect, Perfect” Nice condo with everything close by! Owners were great to deal with and as stated it would be . We plan on visiting again and would recommend this place to anyone.

Match: High chair

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$271

Siesta Key - Beachfront Condo - 2 BR – Free Boat Docks - Renovated!

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great Experience” This condo is well kept, clean and looks directly onto the Gulf of Mexico. We liked it because the furniture is up to date and replaced when it becomes worn. We also love the fact it is within walking distance of a good restaurant. In fact there is nothing about this rental that we don't like and that is why we return there year after year. A great choice for you to start a great experience!

Match: High chair

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Price per night from

$266

Siesta Key - 2BR - Beachfront Condo on Crescent Beach - Heated Pool - Tennis Ct

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$303

Fishermans Cove FC Unit 310B 2

Gulf Gate Estates condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$311

Magnificent Bayfront Condo - Resort Living on the Bay

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$160

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

Fishermans Cove FC Unit 205B *

Gulf Gate Estates condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$266

Tropical Breeze Triple Cottages, Sleeps 16

Sarasota house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 16

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Price per night from

$681

Siesta key Guest House 5 star on the water Private

Siesta Key guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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Price per night from

$229

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