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Southold Vacation Rentals with hot tub(199)

199 Results
  • 6 BR,
  • 6 BA,
  • Sleeps 10
3 - 7 night min stay
(38)
  • 7 BR,
  • 6 BA,
  • 2 HF BA,
  • Sleeps 14
7 - 14 night min stay
(8)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 7
(13)
  • 8 BR,
  • 6 BA,
  • 1 HF BA,
  • Sleeps 16
3 - 6 night min stay
2 Reviews
  • 7 BR,
  • 5 BA,
  • Sleeps 13
1 - 7 night min stay
(5)
$1,300
per night
2 - 6 night min stay
  • 5 BR,
  • 4 BA,
  • Sleeps 8
2 - 6 night min stay
2 Reviews
$857 - $1,267
per night
1 - 30 night min stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
1 - 30 night min stay
2 Reviews
$1,429 - $2,857
per night
2 - 7 night min stay
  • 6 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 16
2 - 7 night min stay
  • 5 BR,
  • 5 BA,
  • Sleeps 10
14 night min stay
$1,290 - $3,490
per night
2 - 4 night min stay
  • 6 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 18
2 - 4 night min stay
$4,000 - $5,000
per night
2 - 3 night min stay
  • 4 BR,
  • 4 BA,
  • Sleeps 12
2 - 3 night min stay
(3)
$18,000
per month
7 - 31 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 5
7 - 31 night min stay
(7)
$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
  • 3 BR,
  • 2 BA,
  • Sleeps 7
5 - 6 night min stay
2 Reviews
$20,000
per week
6 - 8 night min stay
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 16
6 - 8 night min stay
$3,500 - $7,000
per week
7 night min stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
7 night min stay
(3)
$2,000 - $3,333
per night
5 - 7 night min stay
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 12
5 - 7 night min stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 6 night min stay
1 Review
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 5 night min stay
(26)
  • 4 BR,
  • 3 BA,
  • Sleeps 7
3 - 14 night min stay
(4)
$5,600 - $9,500
per week
7 night min stay
  • 6 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
7 night min stay
(15)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
13 - 31 night min stay
$750 - $1,167
per night
3 - 7 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night min stay
(6)
$7,000
per week
14 night min stay
  • 5 BR,
  • 4 BA,
  • Sleeps 12
14 night min stay
$1 - $4,250
per night
1 - 3 night min stay
  • 9 BR,
  • 6 BA,
  • 4 HF BA,
  • Sleeps 32
1 - 3 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 night min stay
(3)
$2,300
per night
1 - 3 night min stay
  • 5 BR,
  • 3 BA,
  • Sleeps 22
1 - 3 night min stay
(4)
  • 6 BR,
  • 3 BA,
  • Sleeps 12
2 night min stay
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Recent Southold Reviews

Great location, lovely family home.

5 of 5
We had a wonderful week at Pat and Gil's home. It really is a home and not just a rental. The pool was great, and the rooftop terrace the perfect spot for sunset drinks. A major bonus was the use of the kayaks to paddle across to Sammis beach. All in all an excellent property in a great residential location near the water yet not far from town.
  • Submitted: Jan 12, 2015
  • Stayed: Sep 2014

Perfect Family Getaway

4 of 5
Beautiful, secluded and well maintained house and property. Our family of 8 enjoyed the pool and ample outdoor seating, as well as the tennis court and large hot tub. Especially helpful and one of the main reasons we plan to return was the extremely accommodating owner who allowed us to bring our two dogs. Plan on getting a beach pass as soon as you arrive - Wainscott beach was exceptional and worth the extra cost. There is even an outdoor structure we used to practice yoga and pilates. If you are a nature lover, the views of the property inside the house are amazing and the log cabin "cozy" feel is perfect for those with children or a romantic couple getaway. Towns of Sag Harbor and East Hampton are both close by and if you are unfamiliar with the area, have great restaurants, markets and shopping.
  • Submitted: Dec 15, 2014
  • Stayed: Aug 2014

Gorgeous & Warm Vacation Home

5 of 5
My friends and I were lucky enough to choose this beautiful home as our home base for a bachelorette party during the off-season in the Hamptons. The home is simply stunning and is well suited and laid out to house 10-12 people comfortably. Even with 12 women getting ready, none of the bathrooms or bedrooms ever felt crowded! The kitchen is gorgeous and the back deck is something out of a magazine with wonderful views of the water. It was a great place to prepare dinners in as the open floorplan allowed for even those in the hottub to converse with people who were grilling or relaxing on the back patio. Jonathan was extremely kind and welcoming during our arrival to the home and spent nearly an hour walking us through how to manage all the technology in the home. The home's 10 minute drive from downtown Sag Harbor made it an excellent location for us! Just far enough away to be quiet but easy to get into the city and not far off of 27 either. Would highly recommend Jonathan and his beautifully maintained property!
  • Submitted: Sep 30, 2014
  • Stayed: Sep 2014