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Holiday Rentals in Osprey, FL

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    1 / 17
    5 of 5 bubbles (1) Excellent
    Osprey
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    1 / 14
    5 of 5 bubbles (1) Excellent
    Osprey
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 16
    Osprey
    2 Bedrooms, 2 Bathrooms, Sleeps 1 | Quick View
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    1 / 17
    Osprey
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Wi-Fi
    • Satellite TV
    • Private Outdoor...
    • Private Garden
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    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... View all property information
    Location Information
    Osprey, Florida 34229
    1 / 25
    Osprey
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Balcony
    • Central Heating
    • Terrace
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Pine Run Tropical Vacation Rental. This end unit condo features a beautiful and peaceful view of the lush landscape from a huge screened lanai. Brand new master bedroom and living room furniture is yours to enjoy. King size bed in master and queen in guest bedroom. The community is located right... View all property information
    Location Information
    Osprey, Florida 34229
    1 / 21
    Osprey
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
    • Wi-Fi
    • Parking
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Pine Run Vacation Rental. This gorgeous and completely renovated unit features an oversized kitchen with granite counters and new appliances. Spacious living room and dining room are tastefully decorated with a nice wooded view. Two large bedrooms with private balconies. Shady shell paths lead to... View all property information
    Location Information
    Osprey, Florida 34229
    1 / 4
    Osprey
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Fully furnished trailer, 10 minutes to Siesta Key. Newly updated, all furnished, walking distance to many restaurants and stores. Quiet area, picnic bench next to creek. Wifi, cable all included except electric. New refrigerator and stove. 2 car carport, enclosed Lanai. No pets, no smoking. Small... View all property information
    Location Information
    Osprey, Florida 34238

    The following rentals are within 10 kilometers of Osprey, Florida.

    1 / 32
    Gulf Gate Branch
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • x
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    About this property
    Villa Cascada is a uniquely configured private home featuring a heated pool/waterfall, 4 bedrooms, 4 bathrooms that sleeps 12, with 2 living areas and 2 kitchens and an almost unbelievable pool courtyard surrounded by lush gardens and a tall privacy wall enclosing the entire property. Each of the... View all property information
    Location Information
    Gulf Gate Branch, Florida
    1 / 33
    Gulf Gate Branch
    6 Bedrooms, 5 Bathrooms, Sleeps 16 | Quick View
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    • Pet-friendly
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    • x
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    About this property
    Welcome to the Sandy Seahorse Cottage! This uniquely configured private home [Sandy Cabana and Seahorse Cabana] is the perfect escape for you and your family and friends. This gorgeous beachy getaway comfortably sleeps 12 with a little room for more!The property has recently been updated with new... View all property information
    Location Information
    Gulf Gate Branch, Florida
    1 / 18
    Gulf Gate Branch
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    Welcome to Serenity Cottage, a gorgeous get away vacation home that boasts all the beauty that Siesta Key has to offer and the best amenities to enjoy our wonderful island! A pristine and elegant home so close to the most beautiful beach in the world most would say, Serenity Cottage offers a... View all property information
    Location Information
    Gulf Gate Branch, Florida
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    1 / 33
    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Pet-friendly
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    • x
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    About this property
    Welcome to La Sirena Casita! This gorgeous freshly remodeled beach casita is the perfect getaway for you and your closest friends and family! The décor is beautifully done and so reminiscent of the seashore and beach [found only in the Point of Rocks area]. It’s clearly luxurious here. Enjoy a... View all property information
    Location Information
    Gulf Gate Branch, Florida
    1 / 22
    Gulf Gate Branch
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
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    About this property
    Welcome to the Sandy Cabana! The Sandy Cabana is one half of the uniquely configured private home called the Sandy Seahorse Cottage and it is the perfect escape for you and your family and friends. This property can be rented separately or combined to accommodate a large party! This side of the... View all property information
    Location Information
    Gulf Gate Branch, Florida
    1 / 35
    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    About this property
    Welcome to Casita Alegria of Villa Fiesta! Enjoy a master bedroom featuring a colorful king size bed (sleeps 2) and en suite master bathroom, and a second bedroom with two twin beds (sleeps 2) and a separate living room with a very comfy, queen size sofa sleeper (sleeps 2) all of which collectively... View all property information
    Location Information
    Gulf Gate Branch, Florida
    1 / 18
    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    The Hibiscus andOrchidVillas are two separate units which can be uniquely configured to create Villa Cascada, an absolutely beautiful and stunning private pool home. Please Note: * These units [Hibiscus &Orchid] can be rented separately. * Combined, these units are called: Villa Cascada(Sleeps 12)... View all property information
    Location Information
    Gulf Gate Branch, Florida
    1 / 35
    Gulf Gate Branch
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    Welcome to the Seahorse Cabana! The Seahorse Cabana is one half of the uniquely configured private home called the Sandy Seahorse Cottage and it is the perfect escape for you and your family and friends. This property can be rented separately or combined to accommodate a large party! This side of... View all property information
    Location Information
    Gulf Gate Branch, Florida
    1 / 31
    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • ?
    About this property
    Welcome to Casita Sonrisa of Villa Fiesta! Enjoy a master bedroom featuring a colorful king size bed (sleeps 2) and en suite master bathroom, and a second bedroom with two twin beds (sleeps 2) and a separate living room with a very comfy, queen size sofa sleeper (sleeps 2) all of which collectively... View all property information
    Location Information
    Gulf Gate Branch, Florida
    1 / 19
    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • ?
    About this property
    The Orchid and Hibiscus Villas are two separate units which can be uniquely configured to create Villa Cascada, an absolutely beautiful and stunning private pool home. Please Note: * These units [Orchid & Hibiscus] can be rented separately. * Combined, these units are called: Villa Cascada(Sleeps... View all property information
    Location Information
    Gulf Gate Branch, Florida
    1 / 20
    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    The Sea Wave and Sea Shell are two separate units which can be uniquely configured to create Villa Brisa Marina, an absolutely beautiful and stunning private pool home. Please Note: * These units [Sea Wave & Sea Shell] can be rented separately. * Combined, these units are called: Villa Brisa... View all property information
    Location Information
    Gulf Gate Branch, Florida
    1 / 24
    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    The Sea Shell and Sea Waveare two separate units which can be uniquely configured to create Villa Brisa Marina, an absolutely beautiful and stunning private pool home. Please Note: * These units [Sea Shell & Sea Wave] can be rented separately. * Combined, these units are called: Villa Brisa... View all property information
    Location Information
    Gulf Gate Branch, Florida
    1 / 30
    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    Welcome to Casita Lima of Villa Margarita! Enjoy a master bedroom featuring a colorful king size bed (sleeps 2) and en suite master bathroom, and a second bedroom with two twin beds (sleeps 2) and a separate living room with a very comfy, queen size sofa sleeper (sleeps 2) all of which collectively... View all property information
    Location Information
    Gulf Gate Branch, Florida
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    1 / 20
    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • ?
    About this property
    The Coral Reef and Star Fish Casitas are two separate units which can be uniquely configured to createVilla Dom Bisa, features its own brand new, private heated pool with “sun shelf” and a three minute walk to the Nation’s finest beach [no major streets to cross]. Please Note: * These units [Coral... View all property information
    Location Information
    Gulf Gate Branch, Florida
    1 / 24
    Gulf Gate Branch
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • ?
    About this property
    Welcome to 'Sea-clusion!' Retreat and relax in this newly hidden gem tucked into the lovely Bianco Sands complex just a SHORT stroll to the warm sands of Crescent Beach. With a newly updated kitchen and bath this delightful 1/1 offers a charming retreat for couples, out of town guests or just you... View all property information
    Location Information
    Gulf Gate Branch, Florida
    1 / 25
    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • ?
    About this property
    Welcome to Casita Salado of Villa Margarita! Enjoy a master bedroom featuring a colorful king size bed (sleeps 2) and en suite master bathroom, and a second bedroom with two twin beds (sleeps 2) and a separate living room with a very comfy, queen size sofa sleeper (sleeps 2) all of which... View all property information
    Location Information
    Gulf Gate Branch, Florida
    1 / 22
    Gulf Gate Branch
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • ?
    About this property
    Villa Brisa Marina or “Sea Breeze” is an exciting 4BR/4BA/2Kit home on our boutique collection of fine vacation homes and it’s sure to be a standout. This home features a brand new heated pool and a four minute walk to the Nation’s finest beach [no major streets to cross]. It’s perfect for families... View all property information
    Location Information
    Gulf Gate Branch, Florida
    1 / 22
    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    The Star Fish and Coral Reef casitas are two separate units which can be uniquely configured to create Villa Dom Brisa, features its own brand new, private heated pool with “sun shelf” and a three minute walk to the Nation’s finest beach [no major streets to cross]. Please Note: * These units [Star... View all property information
    Location Information
    Gulf Gate Branch, Florida
    1 / 21
    Gulf Gate Branch
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    Villa Dom Brisa or “Sun Breeze” is another beautifully decorated, exciting new 4BR/4BA/2Kit home recently added to our boutique collection of fine vacation homes at The Cottages. This home is part of the Las Brisa complex of two beautiful 4-BR homes offering unique sleeping combinations to larger... View all property information
    Location Information
    Gulf Gate Branch, Florida
    1 / 25
    Gulf Gate Branch
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    Villa Fiesta is a vibrant, festive newly decorated four bedroom/four bathroom/two kitchen pool home with only a 4 minute walking distance to the gorgeous Siesta Key beach access for Point of Rocks. Point of Rocks is the most notable beach access for sunbathing, paddleboarding, kayaking, snorkeling... View all property information
    Location Information
    Gulf Gate Branch, Florida
    1 / 34
    Gulf Gate Branch
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    Villa Margarita is a vibrant, festive newly decorated four bedroom/four bathroom/two kitchen pool home with only a 4 minute walking distance to the gorgeous Siesta Key beach access for Point of Rocks. Point of Rocks is the most notable beach access for sunbathing, paddleboarding, kayaking,... View all property information
    Location Information
    Gulf Gate Branch, Florida