House holiday rentals in Shelter Island
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Top-rated house rentals in Shelter Island
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Shelter Island
House rentals with a pool
Home in East Hampton
4.87 out of 5 average rating, 188 reviewsHeated Saltwater Pool, Walk to Beach, Dog Friendly
2–9 Dec
Home in Sag Harbor
4.82 out of 5 average rating, 132 reviewsNew! Sag Harbor Village Pool, Hot Tub &Beach House
16–23 Nov
Home in Cutchogue
4.96 out of 5 average rating, 190 reviewsStunning Vinyard Views - Spring Special $475/Nt!
24 Feb – 3 Mar
Home in East Hampton
4.92 out of 5 average rating, 128 reviewsHeated pool, games room, near beach, kid-friendly
23–30 Oct
Home in East Marion
4.95 out of 5 average rating, 104 reviews* Restored Farmhouse on the North Fork
3–10 Jun
Home in Watermill
4.88 out of 5 average rating, 128 reviewsModern House close to the beach
19–26 Dec
Home in Cutchogue
4.87 out of 5 average rating, 116 reviewsThe Perfect North Fork Escape
3–10 Oct
Home in Manorville
4.99 out of 5 average rating, 200 reviewsUltimate House with Heated Pool, Hot Tub and Sauna
13–20 Oct
Weekly house rentals
Home in East Hampton
4.94 out of 5 average rating, 202 reviewsPrivate beach Historical House with large property
16–23 Mar
Home in Shelter Island
4.92 out of 5 average rating, 73 reviewsFamily Friendly Island Home
5–12 May
Home in East Marion
4.83 out of 5 average rating, 6 reviewsPrivate North Fork Cottage- Walk to Beach!
5–12 Nov
Home in Greenport
4.98 out of 5 average rating, 85 reviewsDesigner's Dream - Charming Boathouse
8–15 Dec
Home in Shelter Island
4.88 out of 5 average rating, 69 reviewsCharming 4BR Cottage on Shelter Island
2–9 Sep
Home in Mattituck
4.92 out of 5 average rating, 92 reviewsModern Farmhouse Steps to Beach & Love Lane
9–16 Nov
Home in Shelter Island
4.97 out of 5 average rating, 76 reviewsModern, spacious SI home with pool
26 Jan – 2 Feb
Home in Greenport
5.0 out of 5 average rating, 10 reviewsThe Sandy Shack - Coastal Escape
13–20 Sep
Private house rentals
Home in Greenport
5.0 out of 5 average rating, 36 reviewsBeachfront Greenport Villa
12–19 Apr
Home in Southold
5.0 out of 5 average rating, 17 reviewsLe Petit Cottage Southold NY
17–24 Apr
Home in Sag Harbor
4.96 out of 5 average rating, 24 reviewsThe Hamptons Casita: Modern Elegance with Pool
3–10 Jun
Home in Greenport
5.0 out of 5 average rating, 19 reviewsThe Corwin House
15–22 May
Home in Southold
5.0 out of 5 average rating, 31 reviewsSalt & Sea House - Near wineries, farms, & beaches
8–15 Jun
Home in Old Saybrook
4.96 out of 5 average rating, 50 reviewsSteps to Beach! *Cozy Cottage* Pet Friendly
13–20 Apr
Home in Sag Harbor
5.0 out of 5 average rating, 22 reviewsPrimely located Sag Harbor Village home
11–18 Jun
Home in Cutchogue
5.0 out of 5 average rating, 24 reviewsNorth Fork paradise between beaches and vineyards
2–9 Jan
Quick stats about house rentals in Shelter Island
Total rentals
100 properties
Rentals with a pool
40 properties have a pool
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
90 properties are a good fit for families
Total number of reviews
1.8K reviews
Nightly prices starting at
$162 SGD before taxes and fees
Destinations to explore
- New City Holiday rentals
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- Rentals with a patio Shelter Island
- Rentals with a washing machine and dryer Shelter Island
- Pet-friendly rentals Shelter Island
- Beachfront rentals Shelter Island
- Fitness-friendly rentals Shelter Island
- Rentals with a firepit Shelter Island
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- Rentals with a fireplace Shelter Island
- Rentals with pools Shelter Island
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- Family-friendly rentals Shelter Island
- Family-friendly rentals Shelter Island
- Monthly Rentals Shelter Island
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