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Holiday Homes near Oscar Scherer State Park

1843 S Tamiami Trl, Osprey, Florida 34229-9663
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    71 Matching Rentals in the Osprey AreaView all 137 rentals
    Osprey
    6.6 kilometres from Oscar Scherer State Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Osprey
    6.6 kilometres from Oscar Scherer State Park
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    New! Five star condo 2BR/2BA  in Osprey/Sarasota county is welcoming you .1 / 31
    (5)Excellent
    Osprey
    3.6 kilometres from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly paradise with heated pool close to Sarasota-Osprey-Nokomis-Venice1 / 17
    (2)Very good
    Osprey
    4.9 kilometres from Oscar Scherer State Park
    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    Perfect Location. Beautiful Waterviews. Heated Pool. 2 BD/2 BA1 / 45
    (1)Excellent
    Osprey
    6.3 kilometres from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Washer
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    • Internet Access
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Osprey, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 BR / 2 BA Condo in Stoneybrook Golf & County Club - Sarasota & Siesta Key1 / 59
    (2)Excellent
    Osprey
    5.1 kilometres from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Hot Tub
    • Patio
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    • Wi-Fi
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    • Sauna
    • Grill
    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
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Osprey
    2.4 kilometres from Oscar Scherer State Park
    1 Bedroom, 1 Bathroom, Sleeps 7 Quick View
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    • DVD Player
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    Pet friendly
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    About this property
    BAY FRONT BEAUTIFUL WATERVIEW. PRIVATE BEACH AREA WITH RELAXING SEATING, HAMMOCKS, GRILL, FIRE PIT, KAYAK LAUNCH ALL ON SITE. PADDLEBOARDS, KAYAKS, BIKES, PONTOON, BOOGIE BOARDS, GOLF CART ALSO ON SITE FOR RENT. SERENE OVERHEAD NIGHT GLOBE LIGHTING. WALKING DISTANCE TO GULF OF MEXICO, RESTAURANTS,...
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    Osprey, Florida
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 7
    Osprey
    2.9 kilometres from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    Pet friendly
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    Smoking allowed
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    Osprey, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Osprey
    4.9 kilometres from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Balcony
    • Cable/satellite TV
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    • Washer
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Osprey, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Osprey
    1.0 kilometres from Oscar Scherer State Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Secure Parking
    • Air Conditioning
    • Grill
    • Private Outdoor Pool (Heated)
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our beautiful and spacious Villa is situated in a quiet subdivision on a large lake front lot with preserve views. The house was re-painted and and furnished in October 2016. It features an open floor plan with two Bedrooms that share a bathroom on one side of the home and the master suite and...
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    Osprey, Florida
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Osprey
    1.1 kilometres from Oscar Scherer State Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Secure Parking
    • Private Garden
    • Air Conditioning
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our beautiful and spacious Villa is situated in a quiet subdivision on a large lake front lot with preserve views. The house was completely renovated and furnished in 2014. It features an open floor plan with two Bedrooms that share a bathroom on one side of the home and the master bedroom and...
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    Osprey, Florida
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Idyllic Casey Key Beach House1 / 19
    (21)Excellent
    Osprey
    2.9 kilometres from Oscar Scherer State Park
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Patio
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    • Private Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Osprey, Florida
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Osprey
    0.6 kilometres from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    Osprey, Florida
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Osprey
    6.7 kilometres from Oscar Scherer State Park
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Wi-Fi
    • DVD Player
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    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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    Osprey, Florida
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Osprey
    6.4 kilometres from Oscar Scherer State Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    * TurnKey photo-verifies this home is professionally cleaned with products approved by the EPA for use against COVID-19. Bookings at this home include a 24-hr buffer between guest stays through June 2020. * ** Please note: Current Executive Orders of the State of Florida do not allow rentals for...
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    Osprey, Florida
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Osprey
    3.9 kilometres from Oscar Scherer State Park
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    • Private Garden
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    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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    Osprey, Florida
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Waterfront Condo, Sleeps 6, Breathtaking Sunsets, Walk To Beach, Family-Friendly1 / 24
    (3)Very good
    Osprey
    7.5 kilometres from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
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    Osprey, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Sarasota Stoneybrook Golf Community - Great Location To Beach1 / 25
    (1)Excellent
    Osprey
    6.2 kilometres from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Osprey, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Beach Front Sophistication and Comfort, 3rd Floor, Free Boat Docks & WiFi1 / 35
    (3)Excellent
    Osprey
    6.6 kilometres from Oscar Scherer State Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Osprey, Florida
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    BEAUTIFULL VACATION HOUSE1 / 19
    (8)Excellent
    Osprey
    6.7 kilometres from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Osprey, Florida
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Spectacular Gulf Views from 2nd Floor unit, Free Boat Docks & WiFi1 / 11
    (4)Very good
    Osprey
    6.6 kilometres from Oscar Scherer State Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
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    Osprey, Florida
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Osprey
    6.6 kilometres from Oscar Scherer State Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Osprey, Florida
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Siesta Key “Condo in Paradise” – Upscale Gulf Front - Best Ground Floor Location1 / 37
    (24)Excellent
    Osprey
    6.6 kilometres from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Osprey, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Corner Unit, Gulf Front on 2nd floor, Free Boat Docks & WiFi1 / 23
    (6)Very good
    Osprey
    6.6 kilometres from Oscar Scherer State Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Osprey, Florida
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Corner Unit, Privacy and Gulf front, First Floor, Free Boat Docks & WiFi1 / 26
    (2)Very good
    Osprey
    6.6 kilometres from Oscar Scherer State Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Osprey, Florida
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Fisherman's Cove  B102 - The Kingston - Private Gulf Front Beach is Open!1 / 19
    (8)Very good
    Osprey
    7.4 kilometres from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Osprey, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Osprey
    6.4 kilometres from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Osprey, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Million Dollar View of Bay Sunrises and Gulf Sunsets-See the Video1 / 23
    (1)Excellent
    Osprey
    6.8 kilometres from Oscar Scherer State Park
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Osprey, Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
    Beach-House, Wonderful Pool area with Natural Waterfall and Jacuzzi, Wi-Fi1 / 46
    (2)Average
    Osprey
    2.7 kilometres from Oscar Scherer State Park
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Osprey, Florida
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    ►BEAUTIFUL Excellent Location Large Executive Home Across from Intracoastal1 / 41
    (6)Excellent
    Osprey
    3.0 kilometres from Oscar Scherer State Park
    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    Osprey, Florida
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 7
    Fisherman's Cove  A113 - The Dominican - Private Gulf Front Beach is Open!1 / 17
    (25)Excellent
    Osprey
    6.6 kilometres from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Osprey, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    337 COMFY  COZY PLACE1 / 21
    (5)Excellent
    Osprey
    3.1 kilometres from Oscar Scherer State Park
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Osprey, Florida
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Exquisitely renovated with direct Gulf front access on First floor – Free Boat D1 / 34
    (5)Excellent
    Osprey
    6.7 kilometres from Oscar Scherer State Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Osprey, Florida
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Corner Unit, Gulf Views of Turtle Beach on 3rd Floor, Free Boat Docks & WiFi1 / 11
    (6)Very good
    Osprey
    6.6 kilometres from Oscar Scherer State Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Osprey, Florida
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Beachfront Siesta Key! Listen to the surf! 2nd floor free WiFi & Boat Dock1 / 44
    (15)Excellent
    Osprey
    6.6 kilometres from Oscar Scherer State Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Osprey, Florida
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Turtle Beach, Beachfront, First Floor, Free Boat Docks & WiFi1 / 11
    (5)Excellent
    Osprey
    6.5 kilometres from Oscar Scherer State Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Osprey, Florida
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Mid-century Waterfront Home with heated pool1 / 28
    (12)Excellent
    Osprey
    0.4 kilometres from Oscar Scherer State Park
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Osprey, Florida
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Direct Gulf View from 3rd Floor with New Furnishings, Free Boat Docks & WiFi1 / 46
    (8)Excellent
    Osprey
    6.6 kilometres from Oscar Scherer State Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Osprey, Florida
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Incredible Gulf View from Lanai or Master -3rd Floor with Boat Dock & Free WiFi1 / 36
    (2)Excellent
    Osprey
    6.5 kilometres from Oscar Scherer State Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Osprey, Florida
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Private Guest House Close To Beach1 / 36
    (6)Excellent
    Osprey
    6.3 kilometres from Oscar Scherer State Park
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Osprey, Florida
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Available January & April 2021!  Spacious Sarasota Home!  Minutes from beach!1 / 22
    (4)Excellent
    Osprey
    6.5 kilometres from Oscar Scherer State Park
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Osprey, Florida
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Welcome To Our 2B/2B Beach Getaway That Is A Home Away From Home!1 / 24
    (29)Excellent
    Osprey
    7.4 kilometres from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Osprey, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Sunrise Cove - Siesta Key Large 3 BR/2 BA, Beautiful Water Views and Beach1 / 15
    (5)Excellent
    Osprey
    6.8 kilometres from Oscar Scherer State Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Sauna
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    Osprey, Florida
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Spacious Waterfront Retreat1 / 40
    (11)Excellent
    Osprey
    0.8 kilometres from Oscar Scherer State Park
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Osprey, Florida
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Perfect Beachfront View of Turtle Beach, Free Boat Docks & WiFi1 / 33
    (2)Very good
    Osprey
    6.6 kilometres from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Osprey, Florida
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    First Class with Gulf View & Sunsets, Free Boat Docks & WiFi1 / 31
    (5)Very good
    Osprey
    6.5 kilometres from Oscar Scherer State Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Osprey, Florida
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Villa Style Condo in Waterside Upscale Gated Community1 / 31
    (5)Excellent
    Osprey
    0.2 kilometres from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Osprey, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Upscale Condominium with Breathtaking Beach View, Free Boat Docks & WiFi1 / 50
    (4)Very good
    Osprey
    6.6 kilometres from Oscar Scherer State Park
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Osprey, Florida
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Waterfront Condo 2 Bedrooms, 2 Baths Between Sarasota and Venice1 / 10
    (6)Excellent
    Osprey
    0.3 kilometres from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Shared Outdoor Pool (Unheated)
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    Osprey, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Romantic comfort from 3rd Floor and Gulf View, Free Boat Docks & WiFi1 / 10
    (6)Excellent
    Osprey
    6.5 kilometres from Oscar Scherer State Park
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Osprey, Florida
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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