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Southold Long Term Vacation Rentals(371)

371 Results
$800 - $2,000
per night
3 - 6 night min stay
  • 4 BR,
  • 2 BA,
  • Sleeps 12
3 - 6 night min stay
(18)
  • 4 BR,
  • 3 BA,
  • Sleeps 8
2 - 3 night min stay
(12)
$700 - $1,900
per night
2 - 3 night min stay
  • 6 BR,
  • 5 BA,
  • Sleeps 10
2 - 3 night min stay
(8)
  • 6 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 12
4 night min stay
(6)
$250 - $371
per night
2 - 7 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 - 7 night min stay
(3)
$700 - $1,214
per night
1 - 7 night min stay
  • 5 BR,
  • 2 BA,
  • Sleeps 10
1 - 7 night min stay
(7)
$375 - $871
per night
2 - 7 night min stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 7 night min stay
(4)
$700 - $1,250
per night
2 - 7 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 - 7 night min stay
(7)
$485
per night
1 - 3 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
1 - 3 night min stay
(6)
$3,000 - $4,500
per week
7 - 14 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
7 - 14 night min stay
(7)
  • 5 BR,
  • 3 BA,
  • Sleeps 9
7 night min stay
(15)
$3,000 - $4,500
per week
7 - 14 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 12
7 - 14 night min stay
$1,300
per night
2 - 6 night min stay
  • 5 BR,
  • 4 BA,
  • Sleeps 8
2 - 6 night min stay
2 Reviews
  • 1 BR,
  • 1 BA,
  • Sleeps 2
2 night min stay
(4)
$500 - $1,000
per night
2 - 31 night min stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 31 night min stay
$3,000 - $4,200
per week
7 - 30 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 7
7 - 30 night min stay
2 Reviews
  • 5 BR,
  • 3 BA,
  • Sleeps 6
7 night min stay
2 Reviews
$4,000 - $5,000
per night
2 - 3 night min stay
  • 4 BR,
  • 4 BA,
  • Sleeps 12
2 - 3 night min stay
(3)
  • 5 BR,
  • 5 BA,
  • Sleeps 10
14 night min stay
$4,772 - $5,943
per week
22 - 106 night min stay
  • 5 BR,
  • 5 BA,
  • Sleeps 10
22 - 106 night min stay
2 Reviews
  • 5 BR,
  • 6 BA,
  • Sleeps 15
14 night min stay
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
$5,000 - $12,000
per week
7 night min stay
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 8
7 night min stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
30 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 - 7 night min stay
(36)
$300 - $450
per night
2 - 7 night min stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 7
2 - 7 night min stay
(9)
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 12
2 - 7 night min stay
(9)
  • 6 BR,
  • 4 BA,
  • Sleeps 16
1 - 2 night min stay
(5)
$350 - $1,571
per night
2 - 14 night min stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 14 night min stay
(12)
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Recent Southold Reviews

Breath Taking!!

5 of 5
I rented this house a few years ago. I would have rented it every year if the owner hadn't decided to stop renting for a few years. When I saw it listed again this year i jumped on it. As soon as you get into the house you can see the most amazing views of the water. The view is so gorgeous it's unbelievable!! Sliding doors lead to an amazing deck, with panoramic views as far as the eye can see. A short walk through a well-manicured lawn leads to steps leading down to your own private beach. The Long Island Sound is beautiful; we enjoyed swimming, fishing and kayaking from our own beach. Just outstanding. A short walk takes you to Plum Gut and a view of the lighthouse. Orient Point is in a great location, surrounded by water and very quaint. Just walking around or star gazing at night is great!! It's also very close to Greenport; Greenport is a town with great shops and restaurants. It's Very enjoyable walking through Greenport. The inside of the house is great with anything you need and has a wonderful heated pool; we had a great time in there as well. Miklos the owner is great to work with and very accommodating!! Overall a 100% perfect vacation. I'm so happy we have an opportunity to return again this year!! Phil
  • Submitted: Apr 20, 2015
  • Stayed: Aug 2014

Very Nice home with fantastic location.

4 of 5
The house is very well maintained inside and it is a fantastic location. Easy to get to Sag and East Hampton. It seems to be well geared toward small children, but is also a lovely 4 bedroom for an adult get-away. The owner does work with you if there are any problems. Keep in mind that if you visit in the winter, the house is set at 50 degrees and takes several hours to heat if it's cold outside. Also make sure the driveway is plowed before you arrive. The large yard looks lovely from what I could see with the snow. I bet it's beautiful in the summer. Very private area on a quite street. I would definitely recommend this house, especially for summer/fall stays.
  • Submitted: Mar 17, 2015
  • Stayed: Mar 2015

Our Christmas Holiday 2014

5 of 5
The house was lovely and fully equipped, my family loved it. It is a big house therefore space is not an issue and it caters to all types of family. Lovely family house.
  • Submitted: Jan 4, 2015
  • Stayed: Dec 2014