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 Sag Harbor
4.85 out of 5 average rating, 250 reviewsExclusive Sag Harbor Compound
Dec 8 – 15
Home in East Hampton
4.92 out of 5 average rating, 128 reviewsHeated pool, games room, near beach, kid-friendly
Oct 23 – 30
Home in East Hampton
4.93 out of 5 average rating, 141 reviews1800 Historical East Hampton Home, 1 Mile to Town!
Oct 28 – Nov 4
Home in Water Mill
4.91 out of 5 average rating, 110 reviewsBeach Barn w/ Sauna and Heated Pool - Dog Friendly
Nov 12 – 19
Home in Cutchogue
4.87 out of 5 average rating, 116 reviewsThe Perfect North Fork Escape
Oct 16 – 23
Home in East Hampton
4.87 out of 5 average rating, 188 reviewsHeated Saltwater Pool, Walk to Beach, Dog Friendly
Nov 21 – 28
Home in Sag Harbor
4.82 out of 5 average rating, 132 reviewsNew! Sag Harbor Village Pool, Hot Tub &Beach House
Nov 8 – 15
Home in East Hampton
4.88 out of 5 average rating, 101 reviewsGorgeous East Hampton Getaway
Oct 10 – 17
Weekly house rentals
Home in Greenport
4.98 out of 5 average rating, 85 reviewsDesigner's Dream - Charming Boathouse
Mar 16 – 23
Home in Shelter Island
5.0 out of 5 average rating, 50 reviewsCASA GYPSEA - a chic and peaceful 3 bedroom house
Oct 14 – 21
Home in Shelter Island
4.92 out of 5 average rating, 73 reviewsFamily Friendly Island Home
Jun 3 – 10
Home in Greenport
5.0 out of 5 average rating, 30 reviewsHistoric Stunner in Heart of Village
Jan 23 – 30
Home in Greenport
4.99 out of 5 average rating, 72 reviewsBeach House in L.I. Wine Country
Oct 24 – 31
Home in Shelter Island
5.0 out of 5 average rating, 10 reviewsSpacious house with pool.
Aug 1 – 8
Home in Shelter Island
4.97 out of 5 average rating, 76 reviewsModern, spacious SI home with pool
Jan 18 – 25
Home in Greenport
5.0 out of 5 average rating, 10 reviewsThe Sandy Shack - Coastal Escape
Nov 6 – 13
Private house rentals
Home in Shelter Island
4.92 out of 5 average rating, 52 reviewsBeautiful beach home with pool & water views!
Dec 7 – 14
Home in Greenport
4.96 out of 5 average rating, 28 reviewsWalk to town, Greenport Village - Harbor Views
Feb 20 – 27
Home in East Marion
4.92 out of 5 average rating, 24 reviewsWaterfront Bungalow w/Private Beach on Peconic Bay
Jun 5 – 12
Home in Greenport
5.0 out of 5 average rating, 10 reviewsThe Saltbox: Outdoor Dining, Fire Pit, Soaking Tub
Sep 24 – Oct 1
Home in East Marion
4.95 out of 5 average rating, 99 reviewsQuiet, Upscale Retreat by the Beach
Oct 3 – 10
Home in Sag Harbor
5.0 out of 5 average rating, 22 reviewsPrimely located Sag Harbor Village home
May 9 – 16
Home in Greenport
4.9 out of 5 average rating, 20 reviewsmodern 3 bedroom home with fireplace
Dec 23 – 30
Home in Greenport
5.0 out of 5 average rating, 3 reviewsWaterfront Greenport Boathouse
Jan 13 – 20
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
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- Rentals with pools Shelter Island Heights
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