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Shelter Island Beach Vacation Rentals(37)

37 Results
  • 4 BR,
  • 3 BA,
  • Sleeps 7
3 - 14 night min stay
(4)
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 6
14 night min stay
1 Review
$5,600 - $6,000
per week
7 - 31 night min stay
  • 5 BR,
  • 3 BA,
  • Sleeps 12
7 - 31 night min stay
1 Review
  • 6 BR,
  • 7 BA,
  • Sleeps 14
3 night min stay
(8)
$12,500 - $25,000
per month
30 - 31 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
30 - 31 night min stay
(3)
$22,000 - $25,000
per month
30 night min stay
  • 4 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 12
30 night min stay
(5)
$425 - $575
per night
2 night min stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
2 night min stay
(6)
$257 - $536
per night
5 - 30 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
5 - 30 night min stay
(3)
  • 5 BR,
  • 2 BA,
  • Sleeps 12
7 night min stay
$325 - $564
per night
2 - 7 night min stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 7 night min stay
(6)
$750 - $929
per night
13 - 30 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
13 - 30 night min stay
  • 4 BR,
  • 4 BA,
  • Sleeps 7
14 night min stay
(4)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night min stay
(3)
  • 5 BR,
  • 3 BA,
  • Sleeps 10
14 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 9
3 - 31 night min stay
1 Review
  • 4 BR,
  • 3 BA,
  • Sleeps 8
$12,000 - $22,000
per month
30 - 31 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
30 - 31 night min stay
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
7 - 30 night min stay
$2,975 - $4,200
per week
7 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
7 night min stay
18 more choices from the HomeAway Network
$2,002 - $4,004
per week
7 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
7 night min stay
(4)
  • 4 BR,
  • 4 BA,
  • Sleeps 8
7 night min stay
(8)
$1,000
per night
7 - 13 night min stay
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
7 - 13 night min stay
$286 - $750
per night
2 - 7 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
2 - 7 night min stay
(3)
$900 - $1,167
per night
15 night min stay
  • 5 BR,
  • 2 BA,
  • Sleeps 9
15 night min stay
(3)
$5,000 - $7,000
per week
7 - 14 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
7 - 14 night min stay
$3,000 - $10,000
per week
7 night min stay
  • 5 BR,
  • 4 BA,
  • Sleeps 12
7 night min stay
(4)
$10,000 - $27,000
per month
30 night min stay
  • 4 BR,
  • 4 BA,
  • Sleeps 5
30 night min stay
$500
per night
3 - 31 night min stay
  • 5 BR,
  • 2 BA,
  • Sleeps 9
3 - 31 night min stay
1 Review
  • 7 BR,
  • 8 BA,
  • Sleeps 20
$1,283 - $10,000
per week
7 - 30 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
7 - 30 night min stay
1 Review
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Recent Shelter Island Reviews

It’s wonderful

4 of 5
It’s wonderful to know that Shelter Island Hideaway has everything you need in a vacation rental. You get the best of both nature and the relaxation of a spa. The walk to the beach is a short one while the multitude of windows is enough to tickle your senses even when you remain indoors.
  • Submitted: Apr 9, 2015
  • Stayed: Mar 2015

Everything in the photos - and so much more!

5 of 5
This property is just absolutely stunning and so wonderful. My husband and I got married on Shelter Island and stayed here for 4 nights during our wedding weekend. We had countless numbers of family and friends filtering in and out throughout those days, and the size was more than accommodating. There are so many different spaces for different groups to socialize in, and we just had a blast. And nobody could get over what a beautiful property it was! It’s so well suited and fun for guests of any age, and every single room inside (there are many!), as well as the pool and the grounds outside are so well kept and spotless. And huge! Little touches like the amazing sound system, the on-site laundry services, all of the kitchen amenities, and the bikes in the garage just make you feel even more at home. And the beautiful porches both upstairs and downstairs are so perfect for relaxing. I enjoyed my coffee every morning on the upstairs balcony with a view of the water. The house is also on such a beautiful and quiet block only steps away from the beach, with the occasional deer families stopping by the front lawn. We just had the most fantastic and memorable few days on Shelter Island, and this house was integral to our good time. Andrew was also always so responsive and helpful in answering all of my questions both before our stay, and during. I can’t thank you enough for sharing your beautiful home with us Andrew! We will be back!
  • Submitted: Sep 29, 2014
  • Stayed: Sep 2014

Beautiful home, perfect vacation

5 of 5
My wife and I were lucky enough to find this home and spend our July out there. Could not have been a more perfect stay. Home is meticulously designed and decorated, an open sunny home during the day and a warm retreat at night. The garden and pool is a perfect oasis and a great place to forget about day to day life and relax. Shelter Island itself is serene and has everything you could want from a summer vacation. Beaches and boating and barbecues or a short trip to the hamptons and the ocean. Hoping to make it back again next summer!
  • Submitted: Sep 9, 2014
  • Stayed: Jul 2014