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 hot tub
Home in East Hampton
4.97 out of 5 average rating, 116 reviewsExplore the Water & Woods at a Relaxing Retreat
Home in East Hampton
4.97 out of 5 average rating, 120 reviewsEast Hampton (walking distance to village)
Home in Cutchogue
4.96 out of 5 average rating, 190 reviewsPrivate Oasis W/Stunning Vinyard And Pool Views
Home in Sag Harbor
4.82 out of 5 average rating, 132 reviewsNew! Sag Harbor Village Pool, Hot Tub &Beach House
Home in Manorville
4.99 out of 5 average rating, 201 reviewsUltimate House with Heated Pool, Hot Tub and Sauna
Home in Wading River
4.97 out of 5 average rating, 460 reviewsYour Zen Retreat
Home in Southampton
4.82 out of 5 average rating, 199 reviewsCozy & Chic Summer Getaway near village/beaches
Home in Center Moriches
4.98 out of 5 average rating, 189 reviewsWalk to beach and playground. Outdoor hot tub.
House rentals with a pool
Home in East Hampton
4.93 out of 5 average rating, 141 reviews1800 Historical East Hampton Home, 1 Mile to Town!
Home in East Hampton
4.92 out of 5 average rating, 128 reviewsHeated pool, games room, near beach, kid-friendly
Home in Cutchogue
4.87 out of 5 average rating, 116 reviewsThe Perfect North Fork Escape
Home in Southampton
4.95 out of 5 average rating, 132 reviewsWaterview, PoolOpenNow! DogsFree+Kayaks+PingPong
Home in Hampton Bays
4.98 out of 5 average rating, 112 reviewsBeach House Feel - newly renovated backyard Oasis
Home in Shelter Island
4.92 out of 5 average rating, 52 reviewsBeautiful beach home with pool & water views!
Home in Shelter Island
5.0 out of 5 average rating, 51 reviewsCASA GYPSEA - a chic and peaceful 3 bedroom house
Home in Shelter Island
4.97 out of 5 average rating, 76 reviewsModern, spacious SI home with pool
House rentals with free parking
Home in Shelter Island
4.92 out of 5 average rating, 73 reviewsFamily Friendly Island Home
Home in Greenport
4.98 out of 5 average rating, 85 reviewsDesigner's Dream - Charming Boathouse
Home in Mattituck
4.92 out of 5 average rating, 93 reviewsModern Farmhouse Steps to Beach & Love Lane
Home in Greenport
5.0 out of 5 average rating, 36 reviewsBeachfront Greenport Villa
Home in Greenport
5.0 out of 5 average rating, 30 reviewsHistoric Stunner in Heart of Village
Home in Sag Harbor
5.0 out of 5 average rating, 92 reviewsSecluded Modern Beach Style House
Home in Sag Harbor
4.96 out of 5 average rating, 25 reviewsThe Hamptons Casita: Summer Meets Perfect Pool
Home in Sag Harbor
5.0 out of 5 average rating, 22 reviewsPrimely located Sag Harbor Village home
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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