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
4.93 out of 5 average rating, 107 reviewsPrivate & Pristine with Pool and Kid’s Playard
Home in North Fork
4.88 out of 5 average rating, 123 reviewsThe Perfect North Fork Escape
Home in East Hampton
4.89 out of 5 average rating, 109 reviewsGorgeous East Hampton Getaway
Home in Hampton Bays
4.94 out of 5 average rating, 121 reviewsPeaceful Retreat in Immaculate Architect’s House
Home in Shelter Island
5 out of 5 average rating, 29 reviewsFamily Friendly Oasis Steps to Water - Heated Pool
Home in Manorville
4.98 out of 5 average rating, 243 reviewsUltimate House with Heated Pool, Hot Tub and Sauna
Home in Mastic Beach
4.93 out of 5 average rating, 118 reviewsGorgeous Waterfront and Indoor Pool Family Oasis!
Home in Southampton
4.95 out of 5 average rating, 151 reviewsWaterview, DogsStayFree! Kayaks, Ping-Pong
Weekly house rentals
Home in Hampton Bays
4.84 out of 5 average rating, 19 reviewsClose to Beach | With Pool | Hampton Bays
Home in East Hampton
5 out of 5 average rating, 85 reviewsSerene East Hampton Escape - 4 Full Suites
Home in North Fork
4.98 out of 5 average rating, 99 reviewsDesigner's Dream - Charming Boathouse
Home in Shelter Island
4.93 out of 5 average rating, 15 reviewsShelter Island GEM Farm House
Home in North Fork
4.92 out of 5 average rating, 12 reviewsNorth Fork Sound Front Home with Pool
Home in Sag Harbor
4.87 out of 5 average rating, 95 reviewsSag Harbor Wonder, 3 bedroom 2 Bath & Heated Pool
Home in Shelter Island
4.88 out of 5 average rating, 24 reviewsNEWLY RENOVATED W/ POOL & FIREPLACE
Home in North Fork
4.97 out of 5 average rating, 36 reviewsLe Petit Cottage Southold NY
Private house rentals
Home in East Hampton
4.96 out of 5 average rating, 48 reviewsEast Hampton Sag Harbor Fringe Pool, Hot Tub, Gym
Home in East Hampton
4.86 out of 5 average rating, 96 reviews4 BD w/ Heated Pool in E Hampton, Fully Furnished
Home in North Fork
5 out of 5 average rating, 9 reviewsStylish Beach Getaway: pool & walking location
Home in North Fork
4.9 out of 5 average rating, 30 reviewsGorgeous home with saltwater pool. Steps to beach!
Home in Shelter Island
5 out of 5 average rating, 6 reviews71
Home in East Hampton
5 out of 5 average rating, 12 reviewsCozy for the Fall- East Hampton Cottage
Home in North Fork
4.96 out of 5 average rating, 26 reviewsWaterfront Beach Cottage
Home in North Fork
4.85 out of 5 average rating, 20 reviewsPrivate North Fork Cottage- Walk to Beach!
Quick stats about house rentals in Shelter Island
Total rentals
100 properties
Nightly prices starting at
$120 before taxes and fees
Total number of reviews
1.6K reviews
Family-friendly rentals
90 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
40 properties have a pool
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- Kid-friendly rentals Shelter Island
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