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Shelter Island Vacation Rentals with air conditioning(84)

84 Results
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
30 night min stay
  • 5 BR,
  • 3 BA,
  • Sleeps 10
7 night min stay
(9)
  • 4 BR,
  • 3 BA,
  • Sleeps 7
3 - 14 night min stay
(4)
  • 4 BR,
  • 2 BA,
  • Sleeps 10
3 night min stay
(6)
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 6
14 night min stay
1 Review
  • 4 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 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
$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)
$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)
  • 3 BR,
  • 2 BA,
  • Sleeps 10
3 - 28 night min stay
1 Review
$350 - $571
per night
2 - 7 night min stay
  • 3 BR,
  • 1 BA,
  • Sleeps 8
2 - 7 night min stay
$2,350
per week
7 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
7 night min stay
(4)
$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
$257 - $536
per night
5 - 30 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
5 - 30 night min stay
(3)
$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
  • 5 BR,
  • 2 BA,
  • Sleeps 12
7 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night min stay
(3)
$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
$500 - $600
per night
3 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 - 7 night min stay
  • 4 BR,
  • 4 BA,
  • Sleeps 7
14 night min stay
(4)
  • 4 BR,
  • 2 BA,
  • Sleeps 8
3 - 30 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
$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,
  • Sleeps 10
14 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

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