House vacation rentals in Shelter Island
Find and book unique houses on Airbnb
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 Hampton Bays
4.94 out of 5 average rating, 120 reviewsPeaceful Retreat in Immaculate Architect’s House
Home in East Hampton
4.89 out of 5 average rating, 109 reviewsGorgeous East Hampton Getaway
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
4.88 out of 5 average rating, 109 reviewsModern East Hampton Home w/ Heated Saltwater Pool
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, 150 reviewsWaterview, DogsStayFree! Kayaks, Ping-Pong
Home in East Hampton
4.98 out of 5 average rating, 128 reviewsExplore the Water & Woods at a Relaxing Retreat
Weekly house rentals
Home in Shelter Island
5 out of 5 average rating, 6 reviews71
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 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 North Fork
4.91 out of 5 average rating, 11 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 Shelter Island
5 out of 5 average rating, 63 reviewsCASA GYPSEA - a chic and peaceful 3 bedroom house
Private house rentals
Home in North Fork
4.98 out of 5 average rating, 53 reviewsVictorian Pearl
Home in North Fork
5 out of 5 average rating, 4 reviewsPeaceful in Peconic
Home in East Hampton
5 out of 5 average rating, 83 reviewsSerene East Hampton Escape - 4 Full Suites
Home in North Fork
4.97 out of 5 average rating, 36 reviewsLe Petit Cottage Southold NY
Home in North Fork
5 out of 5 average rating, 37 reviewsImmaculate NOFO Beach House Steps from Beach
Home in North Fork
5 out of 5 average rating, 22 reviewsNoFo Family Beach House — Walk To Private Beach
Home in Sag Harbor
4.97 out of 5 average rating, 30 reviewsThe Hamptons Casita: Modern Elegance Meets Cozy
Home in East Hampton
4.96 out of 5 average rating, 25 reviewsPrivate Beach With Exceptional Light
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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- Family-friendly rentals Shelter Island
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