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Holiday Homes in Osprey

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    Osprey is popular with travellers just like you. Don’t let them get your perfect place first—book today!
    All 16 Rentals in Osprey
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    Welcome to the Paradise1 / 17
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Patio
    • Grill
    • Washer
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Dear Renter, I am Beya, the owner and I'm offering authentic villas in the natural environment on Palmer Ranch. The villa is a spacious house with stunning garden with palm and pine trees. The location is just perfect, Mall, restaurants, and park are located just minutes drive, sparkling Siesta Key...
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    Osprey, Florida 34238
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pet friendly paradise with heated pool close to Sarasota-Osprey-Nokomis-Venice1 / 17
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Private Garden
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 December 2017
    We had a great stay for the month and plan to come again. Great location midway between our favorite beaches, Caspersen, Casey Key and Siesta Key. Very private lanai and pool...
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    About this property
    Absolutely the best value for your vacation dollar in the Sarasota-Osprey-Nokomis-Venice area ! This newly renovated pet friendly paradise is a single family 3 br - 2 bath home with heated pool that has it all. Large, extremely well equipped kitchen with granite countertops, double convection...
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    Osprey, Florida 34229
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 BR / 2 BA Condo in Stoneybrook Golf & County Club - Sarasota & Siesta Key1 / 15
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Hot Tub
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Sauna
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 June 2018
    The location is amazing! The condo was super clean and very family friendly. I loved the community with multiple pools and the awesome clubhouse. It was just a short drive or...
    Reviewed 25 May 2018
    There was not a single unmet need the entire week. This unit is clean, comfortable, and serene. The kitchen has everything, so we cooked a lot. From the beach towels, cooler...
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    About this property
    Stoneybrook Golf & Country Club is a gated community on Palmer Ranch with a fully renovated clubhouse with fine and casual dining, close proximity to Siesta Key's world-famous beaches, shops, restaurants, and Sarasota's active arts communities. This unit is a ground-floor end/corner unit with extra...
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    Osprey, Florida 34238
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for that spacious vacation home located just minutes from local beaches and shopping. Well this is the perfect home for you. Located in south Sarasota in the community of The Isles on Palmer Ranch you get the best of both worlds, short driving distance to the beaches and also located off...
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    Osprey, Florida 34238
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to this charming 2 bedroom townhome located in Bay Street Community. This rental is conveniently located in Osprey, FL, close proximity to Sarasota and Venice. The amenity-rich community features a clubhouse, community pool, fitness center, and playground. Enjoy the Florida lifestyle plus...
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    Location Information
    Osprey, Florida 34229
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 3 Bedroom, 2 Bath home with split plan in South Sarasota Bay Community. Access to tennis courts, heated swimming pool and lots of social activities. Harbor Front community with water access, and 15 minute drive to Nokomis Beach, close to Siesta Beaches as well. Shopping nearby and...
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    Location Information
    Osprey, Florida 34229
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
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    About this property
    Your spacious and fully equipped vacation Condo here in Sarasota, Florida is located in the beautiful Stoneybrook Golf and Country Club of Sarasota. This community is only a short distance to Siesta Key and provides easy access to premier shopping, dining, and entertainment. This community...
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    Location Information
    Osprey, Florida 34238
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • Parking
    • Internet Access
    • Terrace
    • Air Conditioning
    • Balcony
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully re-modeled 2nd floor unit on Turtle Beach! Sit on your lanai and enjoy the amazing views of the Gulf of Mexico. Complex offers shuffle board, heated pool, boat docks by application and a prime location on Turtle Beach. Enjoy Sunday Brunch at O'Pheila's on the water just a short walk...
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    Osprey, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Central Heating
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunrise Cove Yacht & Racquet Club is the most scenic, relaxing vacation spot on Siesta Key, a barrier island separating the Gulf of Mexico from Sarasota Bay. Located at the quiet end of Siesta Key, across from Turtle Beach, every unit has a direct water view. Nearby Siesta Beach was voted The Best...
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    Osprey, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunshine awaits at this 3BR/2BA Sarasota home for six guests, featuring brand new updates and tranquil landscaping. Spend leisurely afternoons on your private patio with BBQ grill, and dine al fresco in your own backyard. Rent kayaks and launch them in the bay, located just a 5-minute walk from...
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    Osprey, Florida 34231
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Air Conditioning
    • Sauna
    • Wi-Fi
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Soak up the sun and surf at Sunrise Cove in this newly remodeled 1-bedroom, 1-bath vacation rental condo. Hosting 4 guests within the 1,000-square-foot interior, this bayfront unit on Florida's famous shoreline is just steps from Turtle Beach and minutes to Siesta Key and Crescent Beach. When...
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    Location Information
    Osprey, Florida 34231
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Parking
    • Wi-Fi
    • Private Garden
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Idyllic beachfront home located on exclusive, unique Casey Key in Sarasota, Florida. Set in lush tropical greenery including 61 palm trees, sea grapes, and Hibiscus plants, just a few backyard steps to a white sand beach and spectacular sunsets on the Gulf of Mexico. Walk to historic Casey Key...
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    Location Information
    Osprey, Florida 34229
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Begin your sunkissed adventures at this 2-bedroom, 1-bathroom vacation rental condo for 4 guests in Siesta Key. This coastal condo boasts all the amenities of home with the luxuries of an upscale resort. Spend your days lounging around the heated community pool or take a short stroll to nearby...
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    Location Information
    Osprey, Florida 34242
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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