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Shelter Island Pet Friendly Vacation Rentals(37)

37 Results
  • 4 BR,
  • 2 BA,
  • Sleeps 10
3 night minimum stay
(6)
  • 5 BR,
  • 3 BA,
  • Sleeps 10
7 night minimum stay
(9)
$357 - $893
per night
3 - 14 night minimum stay
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 14 night minimum stay
1 Review
$5,000
per week
14 - 30 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
14 - 30 night minimum stay
$425 - $575
per night
2 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
2 night minimum stay
(4)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
(4)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 28 night minimum stay
1 Review
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 6
14 night minimum stay
1 Review
  • 3 BR,
  • 3 BA,
  • Sleeps 7
  • 5 BR,
  • 3 BA,
  • Sleeps 10
  • 5 BR,
  • 4 BA,
  • Sleeps 10
(4)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
$3,000
per week
14 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 3
14 night minimum stay
$2,975 - $4,200
per week
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
$500 - $1,000
per night
1 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
1 - 7 night minimum stay
1 Review
  • 4 BR,
  • 1 BA,
  • Sleeps 15
2 - 3 night minimum stay
2 Reviews
  • 3 BR,
  • Sleeps 5
2 - 7 night minimum stay
1 Review
$1,800
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
1 Review
$3,000 - $4,500
per week
7 night minimum stay
  • 5 BR,
  • 4 BA,
  • Sleeps 12
7 night minimum stay
(4)
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
$250 - $329
per night
3 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 10
3 - 7 night minimum stay
(5)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
5 night minimum stay
(9)
$3,250 - $5,100
per week
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
7 night minimum stay
(7)
$3,500 - $5,500
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 7
  • 5 BR,
  • 2 BA,
  • Sleeps 9
(3)
$500 - $800
per night
5 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
5 - 7 night minimum stay
  • 3 BR,
  • Sleeps 8
3 - 7 night minimum stay
2 Reviews
  • 3 BR,
  • 2 BA,
  • Sleeps 7
1 Review
  • 7 BR,
  • 6 BA,
  • 1 HF BA,
  • Sleeps 16
14 night minimum stay
2 Reviews
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Recent Shelter Island Reviews

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

Beautiful Serene Retreat

5 of 5
The pictures don't capture what a lovely and surprising home this is nor how spectacular its setting. The landscaping, the views of the creek, the subtle winningness of the architecture...a great experience. We found the house warm and artfully arranged with stylish and comfortable furniture and good artwork. The overall effect is clean and organized but in an unfussy way, plus a great kitchen that would please a serious chef, all perfect for an enlightened beach house. It was such a treat to wake up to the dreamy views of the creek after a night of restful sleep on the exceptionally comfortable king-size bed. Though the weather during our stay was great - and there is plenty to do on Shelter Island/Hamptons - at times we enjoyed just lounging around the house and deck, reading, cooking, paddling around in the canoe & kayaks...we had to motivate ourselves to leave. On the one rainy day, we were happily occupied with various fun activities in the house - playing games, exercising in the basement workout room and browsing through the wonderful selection of movies on the Roku TV system. We can only imagine how cozy it would be to huddle around the fireplace in the winter months! Meanwhile, the location - minutes from ferry, beaches, shops and restaurants - could not be more convenient. The house is an easy 5-minute drive from the famed Vine Street Café and a short ferry ride away from wineries on the North Fork and the lovely, low-key town of Sag Harbor on the South Fork. The owners are super pleasant and accommodating. They left well-written notes detailing their home and Shelter Island attractions which certainly made our lives a lot easier. This is a dream of a vacation home. We look forward to our return.
  • Submitted: Sep 9, 2014
  • Stayed: Aug 2014

Stunning, fabulous location, GREAT HOUSE

5 of 5
What can I say except I am VERY picky when it comes to rental homes and this property is even better in person than any picture would do it justice, and it hands down beat my high expectations. Each room has been decorated in stunning furnishings, lighting, the right balance of classic and modern. The screened in porch was a great place to start the day with coffee and baked goods purchased on the island, and NOTHING beats getting on the ferry for the short crossing, its like all the stress goes away. I will for sure be renting this property again!
  • Submitted: May 6, 2014
  • Stayed: May 2014