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Southold Holiday Vacation with Pools

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    C$739 Average
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    C$0C$1,000+
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    Travellers to Southold are booking April dates now. Secure your vacation rental today, and have the perfect trip.
    6 Matching Rentals in the Southold AreaView all 42 rentals
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    Beautiful Classic North Fork Home, wrap around porch, pool, walk to beach1 / 19
    (1)Excellent
    Southold
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    The following rentals are within 10 kilometres of Southold.
    Waterfront Condo C204 at The Cliffside Resort1 / 14
    (11)Excellent
    Greenport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Cutchogue
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Greenport
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Outdoor Dining Area
    • Wi-Fi
    • Patio
    • Parking
    • Grill
    • Children's Pool
    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Historic home in Greenport Village walking distance to restaurants, water, shopping etc..bike or short drive from vineyards. Large yard with outdoor patio with BBQ and outdoor shower. 2 family home with two separate duplex units that can be rented separately or together. Perfect for family...
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    Location Information
    Greenport, North Fork 11944
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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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