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Holiday Vacation with Pools in Osprey, FL and nearby

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    1 / 17
    3 of 5 bubbles (1) Average
    Osprey
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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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 / 21
    Osprey
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    The following rentals are within 10 kilometres of Osprey, Florida.

    1 / 23
    Gulf Gate Branch
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Seaclusion Welcome to Seaclusion! Please Note: Sleeps 2: Q This is a 1br unit in the Bianco Sands Complex. If this unit is not available, please contact us for the availability of another comparable one! Retreat to this amazing “Sea”-cluded gem tucked into the lovely Bianco Sands complex- just a... View all property information
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    Gulf Gate Branch, Florida
    1 / 39
    Gulf Gate Branch
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Serenity Cottage Welcome to Serenity Cottage! Please Note: There is a 7 night minimum stay per SRQ ordinance. If this unit is not available, please contact us for the availability of another comparable one! A pristine and elegant home so close to the most beautiful beach in the world most would... View all property information
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    Gulf Gate Branch, Florida
    1 / 23
    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Sea Wave Casita 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... View all property information
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    Gulf Gate Branch, Florida
    1 / 25
    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    La Sirena Casita Welcome to Sirena Casita! Please Note: Sleeps 6: K, 4T This is a 2br unit in the Bianco Sands Complex, next to the beautiful pool courtyard. If this unit is not available, please contact us for the availability of another comparable one! This gorgeously remodeled beach casita is... View all property information
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    Gulf Gate Branch, Florida
    1 / 30
    Gulf Gate Branch
    6 Bedrooms, 6 Bathrooms, Sleeps 16 | Quick View
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    Sandy Seahorse Cottage Welcome to the Sandy Seahorse Cottage! Please Note: Sleeps 16: 2K, 2Q, 4T, 2QAB These units [Sandy Cabana & Seahorse Cabana] can be rented separately. This uniquely configured private home [Sandy Cabana and Seahorse Cabana] is the perfect escape for you and your family and... View all property information
    Location Information
    Gulf Gate Branch, Florida
    1 / 42
    Gulf Gate Branch
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Villa Cascada 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.... View all property information
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    Gulf Gate Branch, Florida
    1 / 23
    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Hibiscus Villa The Hibiscus and Orchid 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 [Hibiscus & Orchid] can be rented separately. Combined, these units are called: Villa... View all property information
    Location Information
    Gulf Gate Branch, Florida
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    1 / 24
    Gulf Gate Branch
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Sandy Cabana Welcome to the Sandy Cabana! Please Note: Sleeps 8- K, K, Q, QAB These units [Sandy Cabana & Seahorse Cabana] can be rented separately. Combined, these units are called: Sandy Seahorse Cottage (Sleeps 16) If one unit is not available, please contact us for the availability of the... View all property information
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    Gulf Gate Branch, Florida
    1 / 29
    Gulf Gate Branch
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Seahorse Cabana Welcome to the Seahorse Cabana! Please Note: Sleeps 8: K, K, 2T, QAB These units [Sandy Cabana & Seahorse Cabana] can be rented separately. Combined, these units are called: Sandy Seahorse Cottage (Sleeps 16) If one unit is not available, please contact us for the availability of... View all property information
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    Gulf Gate Branch, Florida
    1 / 25
    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Casita Salado 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... 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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    Casita Lima 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... View all property information
    Location Information
    Gulf Gate Branch, Florida
    1 / 23
    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Sea Shell Casita The Sea Shell and Sea Wave 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 Shell & Sea Wave] can be rented separately. Combined, these units are called: Villa... View all property information
    Location Information
    Gulf Gate Branch, Florida
    1 / 45
    Gulf Gate Branch
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Villa Dom Brisa 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... View all property information
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    Gulf Gate Branch, Florida
    1 / 30
    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Casita Alegria 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... View all property information
    Location Information
    Gulf Gate Branch, Florida
    1 / 29
    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Casita Sonrisa 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... View all property information
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    Gulf Gate Branch, Florida
    1 / 24
    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Orchid Villa 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... View all property information
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    Gulf Gate Branch, Florida
    1 / 48
    Gulf Gate Branch
    4 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    About this property
    Villa Fiesta 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,... View all property information
    Location Information
    Gulf Gate Branch, Florida
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    1 / 35
    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Coral Reef Casita The Coral Reef and Star Fish Casitas are two separate units which can be uniquely configured to create Villa 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:... View all property information
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    Gulf Gate Branch, Florida
    1 / 25
    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Star Fish Casita 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:... View all property information
    Location Information
    Gulf Gate Branch, Florida
    1 / 41
    Gulf Gate Branch
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Villa Margarita 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,... View all property information
    Location Information
    Gulf Gate Branch, Florida
    1 / 43
    Gulf Gate Branch
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Villa Brisa Marina 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... View all property information
    Location Information
    Gulf Gate Branch, Florida