House vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Shelter Island house rentals
House rentals with a pool
Home in East Hampton
4.92 out of 5 average rating, 131 reviewsHeated pool, games room, near beach, kid-friendly
Home in East Hampton
4.87 out of 5 average rating, 190 reviewsHeated Salt Water Pool, Walk 2 Beach, Fence 4 Pup
Home in Water Mill
4.91 out of 5 average rating, 111 reviewsBeach Barn w/ Sauna and Heated Pool - Dog Friendly
Home in North Fork
4.96 out of 5 average rating, 191 reviewsPrivate Oasis Stunning Views 7/6 - 7/20 Available
Home in Watermill
4.88 out of 5 average rating, 130 reviewsModern House close to the beach
Home in Manorville
4.99 out of 5 average rating, 211 reviewsUltimate House with Heated Pool, Hot Tub and Sauna
Home in East Hampton
4.97 out of 5 average rating, 117 reviewsExplore the Water & Woods at a Relaxing Retreat
Home in North Fork
4.87 out of 5 average rating, 117 reviewsThe Perfect North Fork Escape
Weekly house rentals
Home in East Lyme
4.96 out of 5 average rating, 107 reviewsWalk to the beach at Black Point, Niantic, Ct
Home in North Fork
4.97 out of 5 average rating, 225 reviewsThe Greenport Bungalow
Home in North Fork
4.98 out of 5 average rating, 109 reviewsStylish Farmhouse in North Fork
Home in North Fork
4.98 out of 5 average rating, 149 reviewsGreenport Village walking distance to all
Home in North Fork
4.98 out of 5 average rating, 87 reviewsDesigner's Dream - Charming Boathouse
Home in Shelter Island
4.92 out of 5 average rating, 73 reviewsFamily Friendly Island Home
Home in Shelter Island
5 out of 5 average rating, 10 reviewsSpacious house with pool.
Home in Sag Harbor
4.9 out of 5 average rating, 77 reviewsSag Harbor Wonder, 3 bedroom 2 Bath & Heated Pool
Private house rentals
Home in North Fork
5 out of 5 average rating, 38 reviewsBeachfront Greenport Villa
Home in North Fork
5 out of 5 average rating, 28 reviewsNorth Fork paradise between beaches and vineyards
Home in North Fork
5 out of 5 average rating, 17 reviewsGorgeous home with heated gunnite pool!
Home in East Hampton
4.95 out of 5 average rating, 56 reviewsOpen Breezy Bungalow with Beach Access By Summer
Home in North Fork
5 out of 5 average rating, 13 reviewsThe Saltbox: Outdoor Dining, Fire Pit, Soaking Tub
Home in Sag Harbor
5 out of 5 average rating, 12 reviewsSunny Sag Harbor Retreat
Home in Sag Harbor
4.96 out of 5 average rating, 26 reviewsThe Hamptons Casita: Summer Meets Perfect Pool
Home in East Hampton
5 out of 5 average rating, 46 reviewsBeach Cottage, East Hampton
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
$120 before taxes and fees
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- Rentals with a washer and dryer Shelter Island
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