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Holiday Rentals with Pools in Osprey

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    Don't let other travellers get your favourite Osprey area holiday rental. You're so close to securing your perfect getaway. Book today.
    14 Matching Rentals in the Osprey AreaView all 23 rentals
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    Pet friendly paradise with heated pool close to Sarasota-Osprey-Nokomis-Venice1 / 17
    (2)Very good
    Osprey
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Osprey
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Welcome to the Paradise1 / 17
    (1)Excellent
    Osprey
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    2 BR / 2 BA Condo in Stoneybrook Golf & County Club - Sarasota & Siesta Key1 / 15
    (2)Excellent
    Osprey
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Hot Tub
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Sauna
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    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 4 weeks ago
    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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    Location Information
    34238, Osprey, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Osprey
    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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    Osprey
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • 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 that sleeps 4 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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    Osprey
    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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    Location Information
    34242, Osprey, Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    The following rentals are within 10 kilometres of Osprey.
    4/3 Pool home 4 miles from Siesta Key Beach1 / 24
    (1)Excellent
    Gulf Gate Branch
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Private Garden
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 January 2018
    This was an amazing place and we couldn't have been happier with our selection. Having a screened in pool attached to the house allowed us easy access everywhere without going...
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    About this property
    U-shaped home surrounding a private pool in the center. 4 bedrooms, living and dining area overlook pool. 40' of glass doors make this true indoor/outdoor living. House sits on a corner lot with 2 driveways. There is room for 2 cars in the rear driveway. House also has a washer/dryer. Split plan...
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    Location Information
    34233, Gulf Gate Branch, Florida
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    LUX CONDOs near beautiful, sparkling Siesta Key Beach.1 / 27
    (1)Excellent
    Gulf Gate Branch
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 October 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
    34238, Gulf Gate Branch, Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Amazing 2 bedrooms, 2 bathroom, with private backyard in a quiet neighborhood. This bright and fully remodeled home is tastefully decorated and well stocked. Conveniently located close walk to Publix and Walmart. Restaurants, cafeterias, spas, beauty salons, bars are around downtown area and only...
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    Location Information
    34233, Gulf Gate Branch, Florida
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Gulf Gate Branch
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Only 8 min. to the #1 Beach in the USA 'Siesta Key Beach'!! Our 'SUPER CLEAN' large 3 bedroom / 2 bathroom condo in a beautiful gated complex. This spacious split plan offers a master bedroom with a walk-in closet, central living room, kitchen, dining room room and two bedrooms on seperate wings...
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    Location Information
    34238, Gulf Gate Branch, Florida
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 Bedrooms, 2 Bathrooms, Sleeps 4 1/2 mile from The Gulf Of Mexico WIFI with HDTV in the living area Pets allowed with permission and pet deposit Absolutely no pets allowed in the pool area Short walk to the beach Private condo 8 units on the complex Looking for a tropical winter get-away or...
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    Location Information
    34231, Gulf Gate Branch, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Washer
    • Hot Tub
    • Parking
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    NEW seasonal rental property available in Sarasota Gulf Gate neighborhood with close proximity to Siesta Key Beach, shopping, restaurants, just about everything ! 2 bedrooms, 3 NEW queen size beds, 2 baths, large NEW screened lanai includng a pool and integrated spa/hot tub! 1 car garage with new...
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    Location Information
    34231, Gulf Gate Branch, Florida
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Gulf Gate Branch
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Balcony
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Grill
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax in comfort at Sea Winds! The unit offers a king bed and sleeper sofa, open patio space and a garden view, perfect for enjoying an outdoor meal. Take a dip in the community pool or shop the neighboring plazas. Beach accesses are 2 blocks in either direction, just a short walk.. Wireless...
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    Location Information
    34242, Gulf Gate Branch, Florida
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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