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Southold Waterfront Vacation Rentals(192)

192 Results
$950 - $2,000
per night
2 - 4 night min stay
  • 4 BR,
  • 2 BA,
  • Sleeps 12
2 - 4 night min stay
(18)
$725 - $1,500
per night
1 - 7 night min stay
  • 5 BR,
  • 4 BA,
  • Sleeps 14
1 - 7 night min stay
(16)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 - 7 night min stay
(5)
$350 - $485
per night
1 - 3 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
1 - 3 night min stay
(6)
$7,500 - $25,667
per week
7 - 30 night min stay
  • 5 BR,
  • 7 BA,
  • 1 HF BA,
  • Sleeps 10
7 - 30 night min stay
(18)
  • 7 BR,
  • 5 BA,
  • Sleeps 13
1 - 7 night min stay
(5)
$18,000
per month
7 - 31 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 5
7 - 31 night min stay
(7)
  • Studio,
  • 1 BA,
  • Sleeps 3
2 - 5 night min stay
$895 - $1,000
per night
3 - 10 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 10 night min stay
(5)
  • 5 BR,
  • 3 BA,
  • Sleeps 10
2 - 7 night min stay
(8)
  • 4 BR,
  • 3 BA,
  • Sleeps 7
4 - 90 night min stay
(4)
$200 - $375
per night
2 - 7 night min stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 7 night min stay
(44)
  • 4 BR,
  • 2 BA,
  • Sleeps 8
2 night min stay
(17)
$800 - $2,900
per week
7 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
7 night min stay
(11)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
4 - 5 night min stay
2 Reviews
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 6
7 - 14 night min stay
1 Review
  • 4 BR,
  • 3 BA,
  • Sleeps 7
3 - 14 night min stay
(4)
  • 5 BR,
  • 3 BA,
  • Sleeps 10
7 night min stay
(9)
$300 - $386
per night
2 - 7 night min stay
  • 3 BR,
  • 1 BA,
  • Sleeps 5
2 - 7 night min stay
$200 - $350
per night
2 - 7 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
2 - 7 night min stay
$25,000 - $35,000
per month
30 - 31 night min stay
  • 4 BR,
  • 4 BA,
  • Sleeps 8
30 - 31 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 7 night min stay
(3)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 7 night min stay
(14)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
14 night min stay
(7)
  • 4 BR,
  • 3 BA,
  • Sleeps 12
3 - 7 night min stay
(19)
  • 4 BR,
  • 2 BA,
  • Sleeps 10
3 - 7 night min stay
(5)
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 14 night min stay
1 Review
$5,000 - $5,833
per week
14 - 31 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
14 - 31 night min stay
$200 - $500
per night
3 - 7 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night min stay
(15)
$400 - $500
per night
2 - 7 night min stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 7 night min stay
(14)
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Recent Southold Reviews

Fantastic and Fun!

5 of 5
Over May 15-17, we had roughly 20 girls stay at the house for a bachelorette. The house was fabulous - There was more than enough room! The kitchen comfortably fit everyone inside, and the majority of the party could sit at the dinner table at once. The backyard patio was a great spot to hang out and lounge. The backyard is huge and although we didn't spend much time on the beach, it definitely would be a great place to throw a bonfire (which was recommended to do by the home owner, Petros). We had a party bus that picked all of the girls up at the house without a problem. Everything was wonderful! We would absolutely rent here again!
  • Submitted: May 18, 2015
  • Stayed: May 2015

It was like living in a fairy tale.

5 of 5
Beautiful cottage surrounded by flowers, water and wonderful sunsets.
  • Submitted: May 18, 2015
  • Stayed: Aug 2014

Great family weekend

5 of 5
Just spent a wonderful family weekend in this beautiful home, idyllic setting, and perfect location. We were seven adults and our dog with room to spare. Can't say enough to recommend this clean and spacious home filled with all of the modern amenities and surrounding beauty one could hope for in a vacation retreat. Right down the road from the best wineries and finer dining options of Southold, the private beach is literally down the back steps. A perfect getaway home in the North Fork area.
  • Submitted: May 17, 2015
  • Stayed: May 2015