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Shelter Island Short Term Vacation Rentals(54)

54 Results
  • 7 BR,
  • 6 BA,
  • 2 HF BA,
  • Sleeps 14
7 - 14 night min stay
(8)
$250 - $371
per night
2 - 7 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 - 7 night min stay
(3)
$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
  • 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)
  • 4 BR,
  • 3 BA,
  • Sleeps 7
4 - 90 night min stay
(4)
$2,000 - $3,333
per night
5 - 14 night min stay
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 12
5 - 14 night min stay
$200 - $250
per night
1 - 3 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
1 - 3 night min stay
$200 - $250
per night
1 - 3 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
1 - 3 night min stay
1 Review
  • 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
  • 6 BR,
  • 4 BA,
  • Sleeps 12
3 - 5 night min stay
2 Reviews
  • 6 BR,
  • 7 BA,
  • Sleeps 14
3 night min stay
(8)
  • 6 BR,
  • 6 BA,
  • 1 HF BA,
  • Sleeps 10
30 night min stay
$425 - $575
per night
2 night min stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
2 night min stay
(6)
$195 - $457
per night
2 - 7 night min stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 7 night min stay
(15)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
2 night min stay
2 Reviews
  • 1 BR,
  • 1 BA,
  • Sleeps 4
2 - 3 night min stay
(17)
  • 3 BR,
  • 2 BA,
  • Sleeps 10
3 - 28 night min stay
1 Review
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
(4)
$350 - $571
per night
2 - 7 night min stay
  • 3 BR,
  • 1 BA,
  • Sleeps 8
2 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 night min stay
$500 - $575
per night
2 - 6 night min stay
  • 4 BR,
  • 1 BA,
  • Sleeps 8
2 - 6 night min stay
1 Review
$1,000 - $3,500
per week
7 - 31 night min stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
7 - 31 night min stay
$2,650 - $6,250
per week
7 - 14 night min stay
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
7 - 14 night min stay
1 Review
$500 - $600
per night
3 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
  • 5 BR,
  • 3 BA,
  • Sleeps 10
14 night min stay
$5,000 - $5,500
per month
30 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
30 night min stay
$250
per night
3 - 4 night min stay
  • 4 BR,
  • 1 BA,
  • Sleeps 8
3 - 4 night min stay
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Recent Shelter Island Reviews

Absolutely perfect getaway

5 of 5
Our weeklong stay was simply perfect. The house is lovely from top to bottom. I LOVED the lap pool. The pictures just don't do this home justice. Staying here feels like true indoor/outdoor living. The natural light is incredible and when the sliding doors are open, and you get a really nice cross breeze. It's close to the downtown Shelter Heights district with restaurants and shops and there's a quiet beach within walking or biking distance from the house. I really loved getting cocktails at Sunset Beach (at sunset of course) and Rams Head Inn brunch's lobster benedict was impeccable (also only a five minute drive from the house). About half of the nights, we fired up the grill and ate on the back deck, which was a nice feature. Right down the road, there's also this fantastic little mini golf place that's super kitschy but fun. Overall, this property was the perfect getaway for our Shelter Island vaca. I would highly recommend it to anyone traveling or summering on the Island.
  • Submitted: Apr 19, 2015
  • Stayed: Aug 2014

Beautiful House that's improved over the years

5 of 5
My wife and I rented this house when we got married and returned with our two kids this year. This house holds a special place in our hearts but it would still be considered a favorite even if you removed the significance. It's beautifully decorated and kept in amazing condition. If your looking for a weekend house to explore the North Folk, this is it. We'll return again.
  • Submitted: Nov 10, 2014
  • Stayed: Oct 2014

LOVELY HOME - WONDERFUL LOCATION!

4 of 5
Lovely views of the harbor and very close to restaurants, cafes and shops - A great house and it was very comfortable for our 'girlfriends' weekend, we were five women who enjoyed relaxing on the front porch chatting with a glass of wine - We did cook one meal and it was great to have access to fresh herbs and tomatoes from the garden in the yard - The caretaker, Tom, even brought us peppers from his own garden that were delicious - Thank you Tom! This is a 5-star property but I gave it a 4-star rating only because of the constant traffic in front of the house going to the ferry - We were there in October so it was considerably less than it must be in the summer months - Even after saying that, I would definitely stay there again! (One suggestion would be to have a full length mirror somewhere in the bedroom area)
  • Submitted: Oct 29, 2014
  • Stayed: Oct 2014