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 East Hampton
4.92 out of 5 average rating, 131 reviewsHeated pool, games room, near beach, kid-friendly
Home in Southampton
4.97 out of 5 average rating, 241 reviewsStunning 3 bed 2 bath home W Pool
Home in East Hampton
4.88 out of 5 average rating, 101 reviewsGorgeous East Hampton Getaway
Home in East Hampton
4.93 out of 5 average rating, 146 reviews1800 Historical East Hampton Home, 1 Mile to Town!
Home in North Fork
4.96 out of 5 average rating, 191 reviewsPrivate Oasis Stunning Views 7/6 - 7/20 Available
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
4.92 out of 5 average rating, 99 reviewsAstounding Watermill 5 Bedroom home with Pool
Home in Southampton
4.95 out of 5 average rating, 133 reviewsWaterview, Pool, DogsStayFree! Kayaks, PingPong
Weekly house rentals
Home in North Fork
4.83 out of 5 average rating, 191 reviewsThe Greenport Townhouse - Amazing Location & Large Backyard
Home in East Hampton
4.94 out of 5 average rating, 208 reviewsPrivate beach Historical House with large property
Home in North Fork
4.98 out of 5 average rating, 87 reviewsDesigner's Dream - Charming Boathouse
Home in Shelter Island
5 out of 5 average rating, 53 reviewsCASA GYPSEA - a chic and peaceful 3 bedroom house
Home in Shelter Island
4.92 out of 5 average rating, 73 reviewsFamily Friendly Island Home
Home in North Fork
5 out of 5 average rating, 4 reviewsQuaint Chalet w/Salt-heated Pool
Home in Shelter Island
4.97 out of 5 average rating, 78 reviewsModern, spacious SI home with pool
Home in North Fork
5 out of 5 average rating, 34 reviewsHistoric Stunner in Heart of Village
Private house rentals
Home in North Fork
5 out of 5 average rating, 16 reviewsRelaxation in Greenport
Home in North Fork
5 out of 5 average rating, 47 reviewsThe Big Easy... A gentle, slow and easy going stay
Home in Shelter Island
5 out of 5 average rating, 18 reviewsFamily Friendly Oasis Steps to Water - Heated Pool
Home in North Fork
5 out of 5 average rating, 38 reviewsBeachfront Greenport Villa
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, 94 reviewsSecluded Modern Beach Style House
Home in Shelter Island
5 out of 5 average rating, 10 reviewsSpacious house with pool.
Home in Sag Harbor
5 out of 5 average rating, 28 reviewsSag Harbor Modern Oasis
Quick stats about house rentals in Shelter Island Heights
Total rentals
190 properties
Rentals with a pool
70 properties have a pool
Pet-friendly rentals
80 properties allow pets
Family-friendly rentals
180 properties are a good fit for families
Total number of reviews
5.5K reviews
Nightly prices starting at
$120 before taxes and fees
Destinations to explore
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- Rentals with pools Shelter Island Heights
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- Family travel hub Tips and inspiration
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