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Holiday Rentals with Pools 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!
    12 Matching Rentals in OspreyView all 18 rentals
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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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    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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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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    34238, Osprey, Florida
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    34238, Osprey, Florida
    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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    34229, Osprey, Florida
    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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    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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    34242, Osprey, Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely 1-bedroom 1-bath condo in Pelican Cove. Vaulted ceilings with view of marina from the lanai. Pelican Cove is located minutes away from shopping and Siesta Key Beach. Unit available for 2 mos during season, at $2200 per mo. 6-mos at $775 per mo. 9-mos at $725 per mo. For additional...
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    34231, Osprey, Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Amazing Siesta Key Seasonal Rental Available December 2018 through April 2019! This bay front home captures the essence of island living. Lush tropical landscaping, attractive entry gates and a calming water feature creates a sense of serenity that draws you in and continues throughout. The...
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    34242, Osprey, Florida
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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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
    34229, Osprey, Florida
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • 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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    34231, Osprey, Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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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
    34242, Osprey, Florida
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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