Osprey Holiday Homes from ฿9,164: Search Top Rental Houses in Osprey

A marina with docked boats, a wooden bridge, and a building with a red roof.

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Our top choices for Osprey holiday homes

The Ashton Hideaway

Sarasota

฿9,164 total

includes taxes & fees

13 Jul - 14 Jul

House, Lakeside | Living area | 39-inch flat-screen TV with digital channels, TV, streaming services

Siesta Heron Suites & Villas

Siesta Key

Christopher Robert

฿11,642 total

includes taxes & fees

14 Jul - 15 Jul

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Top Osprey Hotel Reviews

Tropical Beach Resorts

8/10 Good

"Staff was friendly. Very helpful. Resort was in a great location. Less than a 3 minute walk to a private beach. A very nice tropical pool oasis was right across from where we were located. We were within walking distance of restaurants and beach shops. The rooms were a little dated but very clean. A little smaller than what we are used too but it was very cozy. We would stay there again."