Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Barn
Cottage
Estate
Farmhouse
House
Apartment
Boat
Bungalow
Cabin
Castle
Chalet
Condo
Hotel
Lodge
Studio
Townhome
Villa
Yacht

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Shelter Island Vacation Rentals with Pool(37)

37 Results
7 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 10
(9)
14 night minimum stay
  • 6 BR,
  • 4 BA,
  • 2 HF BA,
  • Sleeps 12
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
2 Reviews
14 - 30 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
  • 4 BR,
  • 2 BA,
  • Sleeps 9
1 Review
7 - 31 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 12
1 Review
2 - 3 night minimum stay
  • 6 BR,
  • 7 BA,
  • Sleeps 14
(7)
2 - 9 night minimum stay
  • 4 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 12
(5)
30 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 Reviews
4 - 14 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 7
(3)
2 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 Reviews
7 - 14 night minimum stay
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
1 Review
6 - 28 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
1 Review
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 - 30 night minimum stay
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
2 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
3 - 7 night minimum stay
  • 5 BR,
  • 4 BA,
  • Sleeps 10
(4)
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
1 Review
18 more choices from the HomeAway Network
7 night minimum stay
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
6 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
1 Review
7 - 31 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 5
7 night minimum stay
  • 5 BR,
  • 2 BA,
  • Sleeps 9
(3)
$1,200
per night
3 - 14 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
1 Review
3 - 14 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 Reviews
  • Studio,
  • 1 BA,
  • Sleeps 14
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
(6)
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
(5)
29 - 30 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 5
Advertisement
 

Recent Shelter Island Reviews

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

Fantastic holiday in this house!

5 of 5
John the owner was wonderfully helpful from start to finish with our holiday to Shelter Island. He was unfazed that we were going to be five mommies and babies for the week and was on hand to answer questions all the time. The garden is beautiful, the rooms all airy and clean (excepting a great room in the basement without light which was great for babies to sleep in!) and from here we were able to do long strolls to Sunset Beach and to the spit on the south of the island. All round fabulous- highly recommended.
  • Submitted: Jun 30, 2014
  • Stayed: May 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