House vacation rentals in Shelter Island Heights
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Top-rated house rentals in Shelter Island Heights
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 Heights house rentals
House rentals with a pool
Home in North Fork
4.97 out of 5 average rating, 201 reviewsPrivate Oasis W/Stunning Vinyard and Pool Views
Home in East Hampton
4.93 out of 5 average rating, 107 reviewsPrivate & Pristine with Pool and Kid’s Playard
Home in Water Mill
4.92 out of 5 average rating, 120 reviewsBeach Barn w/ Sauna and Heated Pool - Dog Friendly
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 East Hampton
4.94 out of 5 average rating, 155 reviews1800 Historical East Hampton Home, 1 Mile to Town!
Home in Southampton
4.95 out of 5 average rating, 151 reviewsWaterview, DogsStayFree! Kayaks, Ping-Pong
Home in New London
4.89 out of 5 average rating, 117 reviewsBeauty and the Beach!
Weekly house rentals
Home in North Fork
5 out of 5 average rating, 23 reviewsElegant Victorian in the Heart of Greenport
Home in North Fork
5 out of 5 average rating, 11 reviewsModern Farmhouse Oasis in GP Village
Home in Shelter Island
4.93 out of 5 average rating, 15 reviewsShelter Island GEM Farm House
Home in Shelter Island
5 out of 5 average rating, 29 reviewsFamily Friendly Oasis Steps to Water - Heated Pool
Home in Shelter Island
5 out of 5 average rating, 12 reviewsBeautiful Home on Shelter Island
Home in Shelter Island
5 out of 5 average rating, 63 reviewsCASA GYPSEA - a chic and peaceful 3 bedroom house
Home in North Fork
5 out of 5 average rating, 29 reviewsRelaxation in Greenport
Home in Shelter Island
5 out of 5 average rating, 5 reviewsIsland beach, fireside retreat - Hamptons!
Private house rentals
Home in North Fork
5 out of 5 average rating, 17 reviewsNewly renovated farmhouse - steps to Village
Home in North Fork
5 out of 5 average rating, 60 reviewsThe Big Easy... A gentle, slow and easy going stay
Home in North Fork
4.9 out of 5 average rating, 30 reviewsGorgeous home with saltwater pool. Steps to beach!
Home in North Fork
4.96 out of 5 average rating, 54 reviews1 block to town, bay views, in Greenport Village.
Home in North Fork
4.92 out of 5 average rating, 12 reviewsNorth Fork Sound Front Home with Pool
Home in Shelter Island
4.88 out of 5 average rating, 24 reviewsNEWLY RENOVATED W/ POOL & FIREPLACE
Home in North Fork
4.95 out of 5 average rating, 38 reviewsWater Views Beach Greenport Getaway
Home in North Fork
4.97 out of 5 average rating, 36 reviewsLe Petit Cottage Southold NY
Quick stats about house rentals in Shelter Island Heights
Total rentals
200 properties
Nightly prices starting at
G$25,035 GYD before taxes and fees
Total number of reviews
5.8K reviews
Family-friendly rentals
190 properties are a good fit for families
Pet-friendly rentals
80 properties allow pets
Rentals with a pool
80 properties have a pool
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- Kid-friendly rentals Shelter Island Heights
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