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Vacation Rentals near Oscar Scherer State Park

1843 S Tamiami Trl, Osprey, Florida 34229-9663
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    Osprey is popular with travelers just like you. Don’t let them get your perfect place first—book today!
    50 Matching Rentals in the Osprey AreaView all 115 rentals
    Osprey
    4.1 miles from Oscar Scherer State Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly paradise with heated pool close to Sarasota-Osprey-Nokomis-Venice1 / 17
    (2)Very good
    Osprey
    3.0 miles from Oscar Scherer State Park
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Five star condo 2BR/2BA  in Osprey/Sarasota county with beautiful pool access!1 / 30
    (5)Excellent
    Osprey
    2.2 miles from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Perfect Location. Beautiful Waterviews. Heated Pool. 2 BD/2 BA1 / 45
    (1)Excellent
    Osprey
    3.9 miles from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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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
    3.2 miles from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Reviewed June 2, 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 May 24, 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
    1.5 miles from Oscar Scherer State Park
    1 Bedroom, 1 Bathroom, Sleeps 7 Quick View
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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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 7
    Osprey
    3.0 miles from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Balcony
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    Osprey, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Osprey
    1.8 miles 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
    Idyllic Casey Key Beach House1 / 19
    (21)Excellent
    Osprey
    1.8 miles from Oscar Scherer State Park
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Osprey, Florida
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Osprey
    0.6 miles from Oscar Scherer State Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Osprey
    0.6 miles from Oscar Scherer State Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
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    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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Comfortable villa with boat dock1 / 18
    (1)Terrible
    Osprey
    0.4 miles from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Osprey, Florida
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Osprey
    4.0 miles from Oscar Scherer State Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    ** Please note: Current Executive Orders of the State of Florida do not allow rentals for guests from New York, New Jersey, or Connecticut. ** * 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...
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    Osprey, Florida
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Available January & April 2021!  Spacious Sarasota Home!  Minutes from beach!1 / 22
    (4)Excellent
    Osprey
    4.0 miles from Oscar Scherer State Park
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Osprey, Florida
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Waterfront Condo, Sleeps 6, Breathtaking Sunsets, Walk To Beach, Family-Friendly1 / 24
    (3)Very good
    Osprey
    4.7 miles 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
    Sarasota Stoneybrook Golf Community - Great Location To Beach1 / 25
    (1)Excellent
    Osprey
    3.8 miles from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Osprey, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    BEAUTIFULL VACATION HOUSE1 / 19
    (8)Excellent
    Osprey
    4.1 miles from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Osprey, Florida
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Welcome To Our 2B/2B Beach Getaway That Is A Home Away From Home!1 / 24
    (30)Excellent
    Osprey
    4.6 miles 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
    Siesta Key “Condo in Paradise” – Upscale Gulf Front - Best Ground Floor Location1 / 37
    (24)Excellent
    Osprey
    4.1 miles 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
    4.2 miles 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
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    Spacious Waterfront Retreat1 / 40
    (11)Excellent
    Osprey
    0.5 miles from Oscar Scherer State Park
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Osprey, Florida
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Fisherman's Cove  B102 - The Kingston - Private Gulf Front Beach is Open!1 / 40
    (8)Very good
    Osprey
    4.6 miles 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
    4.0 miles 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
    Villa Style Condo in Waterside Upscale Gated Community1 / 31
    (5)Excellent
    Osprey
    0.1 miles from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Osprey, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Million Dollar View of Bay Sunrises and Gulf Sunsets-See the Video1 / 23
    (1)Excellent
    Osprey
    4.2 miles 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
    1.6 miles from Oscar Scherer State Park
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Osprey, Florida
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    ►BEAUTIFUL Excellent Location Large Executive Home Across from Intracoastal1 / 41
    (6)Excellent
    Osprey
    1.8 miles from Oscar Scherer State Park
    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    Osprey, Florida
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 7
    Fisherman's Cove  A113 - The Dominican - Private Gulf Front Beach is Open!1 / 17
    (26)Excellent
    Osprey
    4.1 miles 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
    (6)Excellent
    Osprey
    1.9 miles from Oscar Scherer State Park
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Osprey, Florida
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Waterfront Condo 2 Bedrooms, 2 Baths Between Sarasota and Venice1 / 10
    (6)Excellent
    Osprey
    0.1 miles from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Osprey, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Mid-century Waterfront Home with heated pool1 / 28
    (12)Excellent
    Osprey
    0.2 miles from Oscar Scherer State Park
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Osprey, Florida
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Stoneybrook Golf & Country Club  - Wonderful Golf & Lake Views !1 / 25
    (8)Excellent
    Osprey
    3.8 miles 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
    Private Guest House Close To Beach1 / 36
    (6)Excellent
    Osprey
    3.9 miles from Oscar Scherer State Park
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Osprey, Florida
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Fisherman's Cove  A114 - The Havana1 / 20
    (8)Excellent
    Osprey
    3.8 miles 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
    2.4 miles from Oscar Scherer State Park
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Osprey
    4.1 miles from Oscar Scherer State Park
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    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
    4.1 miles from Oscar Scherer State Park
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Book your stay in sunny Sarasota at this spacious vacation rental home for 6-8. The property boasts 2 bedrooms, 3 full bathrooms, and a very large backyard with mango, avocado, tamarind, and dragon fruit trees. The south Sarasota home is ideally located right off of Tamiami Trail, so you can access...
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    Osprey, Florida
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 8
    Beautiful Water Views, Quiet South End, Walk to the Beach1 / 22
    (6)Excellent
    Osprey
    4.0 miles from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Location Information
    Osprey, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Osprey
    4.2 miles from Oscar Scherer State Park
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    About this property
    Blissful days on the beach, easygoing mornings on Little Sarasota Bay, and relaxing afternoons on the spacious lanai await at this 3-bedroom, 2-bath house! The airy vacation rental features a full kitchen, a lush private backyard, and a spacious lanai for a stress-free stay. Vamo Drive Park boasts...
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    Osprey, Florida
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    Brand New Tastefully Decorated Town home, Located in Osprey, FL. Osprey 011 / 29
    (2)Excellent
    Osprey
    2.0 miles from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Location Information
    Osprey, Florida
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    The following rentals are within 5 miles of Osprey.
    Gulf Gate Estates
    4.6 miles from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Bay Tree Club is a premier beach property on the south end of Siesta Key in Sarasota, Florida, located on the Gulf of Mexico with a private beach and private beach access to Turtle Beach. Situated on the top floor (5), this updated gorgeous condo has 2 beautifully furnished bedrooms with 2 ensuite...
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    Gulf Gate Estates, Sarasota
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Gulf Gate Estates
    4.6 miles from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    WOW! Tortuga Turtle Beach Condo is a gem of all gems on south Siesta Key! Sink your toes into the warm sand of Turtle Beach in only a few minutes thru a private beach access located just behind the building....walk into the elevator....step outside the access door....walk to the back of the...
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    Gulf Gate Estates, Sarasota
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Gulf Gate Estates
    4.2 miles from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Accurately named, SUNRISE COVE offers incredible BAY sunrises morning after morning....but wait there's more....a 5 minute walk across the street will land you onto Turtle Beach for incredible evening sunsets! Having the option of the bay and the beach is a dream come true! Lay out in the sun,...
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    Location Information
    Gulf Gate Estates, Sarasota
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Laurel
    3.4 miles from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sea Esta on Shakett Creek Treat your family and friends to some riverfront fun with this northern Nokomis house, with boating in Shakett Creek, a private lanai with sweeping views of the water, and a private heated pool. Dogs are welcome for a small nightly fee. Shops and restaurants are a...
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    Laurel, Florida
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Casey Key
    1.5 miles from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    About this property
    Amazing live-aboard opportunity and a fully self-contained houseboat. Very private was all the necessary amenities and many extras. On-site also for availability and use for a small fee are paddle boards, kayaks, bicycles, and an electric car like a golf cart. Gulf of Mexico access across the...
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    Location Information
    Casey Key, Florida
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Gulf Gate Estates
    3.7 miles from Oscar Scherer State Park
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Our Beach Cottage is the perfect home for your vacation. We are located about 3 miles to Siesta Key where you can enjoy the #1 Beach, great restaurants, entertainment and much more. You can also enjoy the a kayak/paddle board launch less than .5 mile from our door. The property is fully fenced for...
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    Gulf Gate Estates, Sarasota
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    LUX CONDOs near beautiful, sparkling Siesta Key Beach.1 / 27
    (1)Excellent
    Gulf Gate Branch
    4.6 miles from Oscar Scherer State Park
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 11, 2017
    The location is great. Really close to the beach. The host is very friendly and helpful. We enjoyed our vacation.
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    About this property
    Dear Renter, I am Beya, the owner with more a decade experience in the vacation rental field. I have been offering authentic condos in the beautiful natural area of the Vintage Grand community. I would be happy to host you in one of my condos.I have down and upstairs floor condos with lake-view or...
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    Location Information
    Gulf Gate Branch, Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Casey Key
    0.6 miles from Oscar Scherer State Park
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Recently remodeled,this welcoming home is situated in the perfect and safest location for the best experience you are looking for! Located just 7 minutes away from Casey Key Beach, 12 minutes to Venice Beach and 17 minutes to the beautiful Siesta Key Beach! It is also very close to I-75 and...
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    Location Information
    Casey Key, Florida
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Casey Key
    1.9 miles from Oscar Scherer State Park
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Nestled on a private island just steps from the Gulf of Mexico, this 2-bedroom, 2-bath vacation rental apartment offers a lovely home base to kick back, relax, and enjoy the sandy shores. The 1,500-square-foot interior features all the comforts of home, while the outdoor patio and gas grill are...
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    Location Information
    Casey Key, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Laurel
    2.6 miles from Oscar Scherer State Park
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Smoking allowed
    About this property
    Get ready for coastal relaxation at this Nokomis vacation rental! This 1-bed, 2-bath house is set on an expansive yard boasting a large pond and a lanai complete with a shared pool area and 2 upscale seating areas! Make the 2.8-mile trip to Nokomis Beach, or travel a bit further to Venice Beach for...
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    Location Information
    Laurel, Florida
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 4
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