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Shelter Island Vacation Rentals with Online Payment(38)

38 Results
7 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 10
(9)
14 - 30 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
14 - 30 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 3 night minimum stay
  • 6 BR,
  • 7 BA,
  • Sleeps 14
(7)
21 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 10
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 30 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
(3)
$2,275 - $3,500
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
(3)
3 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
1 Review
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
7 night minimum stay
  • 6 BR,
  • 4 BA,
  • Sleeps 14
2 Reviews
3 - 14 night minimum stay
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
1 Review
2 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
1 Review
6 - 28 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
1 Review
31 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 14 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
(7)
7 - 30 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
1 Review
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
(3)
27 - 30 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
31 night minimum stay
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 6
1 Review
17 more choices from the HomeAway Network
3 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 10
(5)
$2,002 - $4,004
per week
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
(3)
4 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 5
7 night minimum stay
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
7 night minimum stay
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
2 - 7 night minimum stay
  • 3 BR,
  • Sleeps 5
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
(9)
$1,700
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
1 Review
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Recent Shelter Island Reviews

GREAT HOUSE, PERFECT LOCATION

5 of 5
What a wonderful find! We've been going to Shelter Island for years, but this was our first time spending a full week with our young kids. The house is a quick walk to town and easily accessible to the best attractions on the island, and yet, it's secluded location offers great privacy. It's a beautiful piece of property on the creek, allowing for a lovely sunset every night. I loved that I was always looking out onto the water. The house is feels large for it's size with nice flow, and a large screened-in porch was a great spot for reading, playing games or just bird watching. Birder or not, you'll find yourself reaching for the bird book to identify those charming little creatures! My favorite spot was the converted one-car garage into a screened in room. We ate dinner out there every night. Having access to the kayak for a quick ride over the the harbor or over to the tall grasses to see the egrets. Our kids loved the bunk beds and we appreciated a nice mattress in the master bedroom! Bring your bikes!
  • Submitted: Jul 23, 2014
  • Stayed: Jun 2014

BEAUTIFUL, CHARMING HOME

5 of 5
We had the pleasure of spending 10 wonderful days at this fully updated, charming farmhouse. The house was extremely well maintained and the English gardens are spectacular. The beds were extremely comfortable, with crisp white bedding and the kitchen was well stocked. The children spent hours in the large, private pool. The home is extremely well located to walk to sunset (crescent) beach and Shelter Island Heights and is also close to the central part of town. There are so many great things to do in Shelter Island: beach, hiking, biking, kayaking, mini-golf, farmer's market, great restaurants and all of it was just minutes away. The owner was very responsive and helpful and made us feel at home. We would love to rent this house again.
  • Submitted: Jul 9, 2014
  • Stayed: Jun 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