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Osterville Pet Friendly Vacation Rentals

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    Travellers to Osterville are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    13 Matching Rentals in OstervilleView all 47 rentals
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Cable/satellite TV
    • DVD Player
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stroll to the village from this lovely three bedrooms, three full bath home. Large open floor plan on first level with kitchen, dining, living room, bedroom and full bath. Go upstairs to two more bedrooms and two additional full baths. There is central air for your comfort as well as a...
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    Osterville, Cape Cod 02655
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    24 South Street1 / 31
    (3)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Wi-Fi
    • Parking
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 6, 2018
    Beautifully decorated traditional Cape house, close to beach, close to village making for ideal Cape vacation. This spacious 4-bedroom is fully equipped top to bottom with...
    Reviewed March 30, 2018
    It is immaculate, well provisioned, comfortable and walking distance to all the wonderful shops, restaurants and beaches of Osterville. I will definitely be back!
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    About this property
    Lovely four bedroom, two bath rental home in the heart of Osterville. Short stroll to village and not far from Dowses Beach with a beach pass provided. Two bedrooms, living room, dining room and sitting area on the first level as well as a full bath. Second level has two bedrooms and second full...
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    Osterville, Cape Cod 02655
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Its always nice to be a short stroll to the village and not far from the beach. This Osterville rental home has these qualities and more. Large open concept kitchen and eating area with TV, formal living room and den with additional flat screen TV, couch and bunk beds for a 4th sleeping area....
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    Osterville, Cape Cod 02655
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Cable/satellite TV
    • Parking
    • Hot Tub
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Robert Paul Properties Luxury collection rental home. Enter the private gated community and once you arrive be surrounded by water in prestigious Oyster Harbors. This Shingle Cottage style home was built in 2004 and comes with a sandy beach area as well as amazing attention to details. Over...
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    Osterville, Cape Cod 02655
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 8
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Private Garden
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to what we affectionately refer to as 'The Black Pearl,' a vintage home located in one of the Cape's most coveted locations. Oyster Harbors is a private island only accessible to residents, club members & guests! A deep water dock with access to fast water in minutes. Enjoy views of...
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    Osterville, Cape Cod 02655
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    6 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great home located between Dowses Beach and Osterville village. There are six bedrooms and four full baths and central air for your comfort. The first level offers a large formal dining room, well-equipped kitchen with a casual eating area, comfortable living room, two full baths, two bedrooms and...
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    Osterville, Cape Cod 02655
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 10
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    94 Waterfield Road1 / 19
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 31, 2018
    We've have used this house several times in different seasons and we always had a perfect experience! The house is conveniently located just minutes from charming Osterville...
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    About this property
    Close to Osterville village and Joshua's Pond, this charming rental home has four bedrooms including a master suite with full bath on second level and three bedrooms and a full bath on first floor. Living room, family room and eat-in kitchen. There is a spacious deck off the kitchen, outdoor shower...
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    Location Information
    Osterville, Cape Cod 02655
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Parking
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wonderful Osterville location just steps to the Marina is known as the 'Windmill House.' This stunning 3 bedroom, 3 bath home is nicely appointed with a soaring two story living room with fireplace, flat screen TV, and French doors to a private patio. There is a 1st floor 2 room suite with bath....
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    Osterville, Cape Cod 02655
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Hot Tub
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Waterfront
    • Patio
    • Private Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Robert Paul Properties Luxury collection rental home. Welcome to Osterville! This spacious newly renovated rental property is located in the gated community of Oyster Harbors with a heated infinity pool, spectacular water views of West Bay and a private dock. Drink your coffee on the terrace,...
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    Osterville, Cape Cod 02655
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Central Heating
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 Bedroom Home in Osterville! Beautiful home with great back yard and expansive deck. 3 bedrooms and 3 full baths, this home also offers a full walkout finished basement with pool table and living room! Laundry on site as well. Window A/C units for those hot summer days. Bring the whole family,...
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    Location Information
    Osterville, Cape Cod 02655
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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