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Southold Pet Friendly Vacation Rentals

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    Travellers to Southold are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    12 Matching Rentals in the Southold AreaView all 42 rentals
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    Beach House In Wine Country; walk to beach, large sun room, outdoor dining1 / 16
    (2)Excellent
    Southold
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Southold
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Southold
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Shorecrest Beach House, 4 bedroom private beach front, new renovation1 / 32
    (3)Excellent
    Southold
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Waterfront
    • Washer
    • Parking
    • Internet Access
    • Air Conditioning
    • Grill
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 30, 2018
    We were absolutely blown away by how lovely our stay was at this beach front cottage right on the water in Southold! From the gorgeous sunsets seen from the porch over the water...
    Reviewed July 24, 2018
    This beach house is located right on the north shore of the long island sound, perfectly placed in the middle of the North Fork close to all the beautiful wineries and breweries...
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    About this property
    Newly renovated with two new full bathrooms, new kitchen and second floor bedroom/family room with glorious views overlooking the Long Island Sound, the Shorecrest Beach House has never looked so good! The Shorecrest beach house is located on a grassy bluff overlooking the ocean and available for...
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    Location Information
    Southold, North Fork 11971
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Southold
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Balcony
    • DVD Player
    • Waterfront
    • Parking
    • Grill
    • Hot Tub
    • Wi-Fi
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This unique country cottage is situated on a spring-fed fresh water lake one block from Kenney's Beach - a sandy Long Island Sound beach staffed by Southold Town lifeguards. Designed to maximize the beauty of its pristine surroundings, the entire back of the house has French doors opening onto a...
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    Location Information
    Southold, North Fork 11971
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    The following rentals are within 10 kilometres of Southold.
    Cutchogue
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Secure Parking
    • Patio
    • Private Garden
    • Washer
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This newly renovated cottage has a spacious living room, large eat-in-kitchen, 2 bedrooms; one with queen-sized bed, the other with two twins, and one full and one half bath. There is a waterview across the street from the relaxing 'pebble lounge' the garden seating area in front of the house....
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    Cutchogue, North Fork 11935
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    The Farmhouse1 / 15
    (1)Very good
    Greenport
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Secure Parking
    • Cable/satellite TV
    • Private Garden
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 6, 2017
    My family rented this house for the holiday week between Christmas and New Years. The house is located within walking distance to town - which was quite great The house has...
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    About this property
    Renovated and tastefully furnished, The Farmhouse features one of the largest wrap around porches in the village and it is enviably located steps away from the town's best restaurants and bars, as well as just 3 short blocks to the beach. The space Just steps away from the center of the Greenport...
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    Greenport, North Fork 11944
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    Greenport
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Private Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Built in 1828 for a ship’s captain, this historic property remains as one of the oldest structures in the village. Original details abound. Large, bright & airy rooms. Brand new furnishings. Perfect for entertaining or a quiet weekend retreat. The Space Located on a tree lined street this...
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    Location Information
    Greenport, North Fork 11944
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    North Fork Beach House on LI Sound1 / 14
    (1)Excellent
    Peconic
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Patio
    • Housekeeping Included
    • Air Conditioning
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 27, 2018
    House had everything we needed to enjoy a vacation at the beach. Great outdoor barbecue area, huge outdoor shower. Sunsets are amazing from the deck!Comfortable beds and...
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    About this property
    Enter a world of tranquility and surround yourself with the beauty of nature! Decorated with an eclectic mix of antique and contemporary furniture, the home has three bedrooms, one bath, dining room, living room with large flat screen tv, sunroom with seating and dining area. Kitchen is remodeled...
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    Peconic, North Fork 11958
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Greenport
    4 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will love this 4 bedroom 4.5 bathroom charmer on a quiet street. Walk to town, shops, carousel LIRR Jitney and ferry to Shelter Island Golf course and beaches 1 mile away. There are over 40 wineries nearby. The front deck has 2 Adirondack chairs to just relax. A full deck off the back over...
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    Location Information
    Greenport, North Fork 11944
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 9
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    Shelter Island Heights
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Terrace
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    For those seeking a peaceful, quiet, zen-like place to spend their vacation or honeymoon, 'The Shelter Island Hideaway Beach Vacation Cottage' is the home for you. The luxurious, waterfront 2-bedroom, 1-bathroom vacation rental cottage offers 1,125 square feet of sheer Caribbean-style elegance....
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    Location Information
    Shelter Island Heights, Shelter Island 11964
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Greenport
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Parking
    • Private Garden
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled steps from the beach, and all that Greenport and the North Fork has to offer, this exquisitely charming 3 bedroom 2 bathroom waterfront home is absolutely delightful.. You’ll love my place because of the views, the location, the people, the ambiance, the outdoors space, and the Saltwater...
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    Location Information
    Greenport, North Fork 11944
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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