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Pet Friendly Holiday Rentals in Osterville

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    AU$1,709 Average
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    Travellers to Osterville are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    15 Matching Rentals in OstervilleView all 53 rentals
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Cable/satellite TV
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    • Hot Tub
    • Wi-Fi
    • Waterfront
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    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
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Robert Paul Properties rental home located in the heart of Crosby Town (North Bay Marina area) perfect summer vacation spot. Spacious kitchen and family room with TV as well as dining area on the way to the living room. 1st floor half-bath/laundry as well as the master bedroom and full bath....
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    Osterville, Cape Cod 02655
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You get home from one of the beaches the complimentary beach pass allows you to visit, then washing off the sand in your enclosed outdoor shower. Relax on the sun splashed outdoor deck with your guests while enjoying a cold refreshing beverage and a delicious meal prepared on the gas grill. In the...
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    Osterville, Cape Cod 02655
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    31 Eel River Road1 / 22
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 June 2018
    We rented here for 2 weeks and loved it. Quintessential Cape Cod! Walking distance to the quant village with lots of cute shops and restaurants. The back porch was perfect for...
    Reviewed 4 April 2018
    What else does one have to say, we had a great stay! With West Bay views, access to the bay, a nice yard and walking to the Crosby's Boat Yard and Osterville village...
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    About this property
    Enjoy sunsets from this charming Cape Cod rental overlooking West Bay with a deeded path for easy access to the water. A comfortable seaside home which is perfectly configured for summer time fun! This four bedroom 3 1/2 bath home is perfectly located in the heart of Wianno and within walking...
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    Osterville, Cape Cod 02655
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    94 Waterfield Road1 / 19
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 August 2019
    My family and I had a wonderful time staying here. There is plenty of space and the backyard and deck were put to great use. It is pindrop quiet and the kitchen is very well...
    Reviewed 1 April 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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    Osterville, Cape Cod 02655
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    17 Indian Trail1 / 51
    (1)Excellent
    9 Bedrooms, 9 Bathrooms, Sleeps 1 Quick View
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    • Grill
    • Internet Access
    • Cable/satellite TV
    • DVD Player
    • Patio
    • Parking
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 August 2019
    I rented this property for a family gathering of 19 people for a week in August. The property is stunning, 7 acres of house, gardens, tennis court on the water in Osterville...
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    About this property
    Quiet luxury on the waters edge. Feel at one with the sand, surf, and sun while luxuriating on your own beach area surrounded by private and lush 26 acres in this exclusive gated paradise that is Oyster Harbors. Complete with a tennis court, beach house, dock and beach area. This property provides...
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    Osterville, Cape Cod 02655
    Holiday Rental House - 9 Bedrooms, 9 Bathrooms, Sleeps 1
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Private Garden
    • Cable/satellite TV
    • Air Conditioning
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    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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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the Windmill house...…. Wonderful Osterville location just steps to the Marina is known as the 'Windmill House.' This stunning three bedroom, three full bath home is nicely appointed with a soaring two story living room with flat screen TV, and French doors to a private outdoor patio....
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    Osterville, Cape Cod 02655
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    271 Westwind Cir1 / 17
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Central Heating
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 July 2019
    We absolutely loved this rental home!!! Well maintained. Loved the finished basement, including a pool table, and back deck with grill. Also had a hammock in the big back yard...
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    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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    Osterville, Cape Cod 02655
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    38A Blossom Avenue1 / 18
    (2)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 days ago
    This house is fantastic. Decorated in great taste, comfortable, bright, and all appliances and bathrooms are like new. Bedrooms and living areas sooo comfortable. Location is...
    Reviewed 22 July 2019
    This home was beautifully decorated with all the amenities of home: Sonos, big screen tv, outdoor grill, Nepresso Coffee maker, Tempurpedic master king bed and a large closet...
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    About this property
    Robert Paul Properties rental home. Walk to town for dinner or a short drive to area Dowses beach. Brand new to rental market and extremely well appointed home in Coastal Osterville Village. First floor has new gourmet kitchen, bedroom, living room as well as full bath and powder room....
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    Osterville, Cape Cod 02655
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    9 Bedrooms, 9 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Robert Paul Properties Luxury Collection Rental home. Feel truly swept away in Old Cape Cod charm and nostalgia at this quintessential coastal estate. Situated on the banks of Seapuit River, between Cotuit and West Bays, you are arguably by the three nicest bodies of water Nantucket Sound has to...
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    Osterville, Cape Cod 02655
    Holiday Rental House - 9 Bedrooms, 9 Bathrooms, Sleeps 12
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Three bedroom carriage house on private oceanfront estate in Wianno section of Osterville. Originally built as stablemen's quarters, this house has been renovated into an adorable cottage-like home. Screened in porch leads to a large living area with hardwood floors, cathedral ceiling, ceiling...
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    Osterville, Cape Cod 02655
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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