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
4.93 out of 5 average rating, 140 reviews1800 Historical East Hampton Home, 1 Mile to Town!
Nov. 26 – Dec. 3
Home in East Hampton
4.97 out of 5 average rating, 116 reviewsExplore the Water & Woods at a Relaxing Retreat
Dec. 4 – 11
Home in East Hampton
4.87 out of 5 average rating, 188 reviewsHeated Saltwater Pool, Walk to Beach, Dog Friendly
Oct. 23 – 30
Home in Sag Harbor
4.81 out of 5 average rating, 108 reviewsSag Harbor Gem, private, 4 Bedrooms, Pool w Summer
Jun. 6 – 13
Home in Cutchogue
4.87 out of 5 average rating, 115 reviewsThe Perfect North Fork Escape
Oct. 4 – 11
Home in Cutchogue
4.96 out of 5 average rating, 190 reviewsStunning Vinyard Views - Spring Special $475/Nt!
Feb. 4 – 11
Home in Hampton Bays
4.98 out of 5 average rating, 112 reviewsBeach House Feel - newly renovated backyard Oasis
Oct. 25 – Nov. 1
Home in Southampton
4.96 out of 5 average rating, 130 reviewsWaterview, PoolOpenNow! DogsFree+Kayaks+PingPong
Mar. 21 – 28
Weekly house rentals
Home in Shelter Island
4.92 out of 5 average rating, 73 reviewsFamily Friendly Island Home
May 12 – 19
Home in Greenport
4.98 out of 5 average rating, 85 reviewsDesigner's Dream - Charming Boathouse
Oct. 13 – 20
Home in Shelter Island
4.88 out of 5 average rating, 69 reviewsCharming 4BR Cottage on Shelter Island
Dec. 17 – 24
Home in Greenport
5.0 out of 5 average rating, 30 reviewsHistoric Stunner in Heart of Village
Jan. 6 – 13
Home in Greenport
5.0 out of 5 average rating, 10 reviewsThe Sandy Shack - Coastal Escape
Sep. 18 – 25
Home in Shelter Island
4.97 out of 5 average rating, 76 reviewsModern, spacious SI home with pool
Feb. 28 – Mar. 7
Home in Greenport
5.0 out of 5 average rating, 70 reviewsBeach House in L.I. Wine Country
Oct. 24 – 31
Home in Greenport
5.0 out of 5 average rating, 16 reviewsRelaxation in Greenport
Mar. 8 – 15
Private house rentals
Home in Shelter Island
5.0 out of 5 average rating, 16 reviewsFamily Friendly Oasis Steps to Water - Heated Pool
May 9 – 16
Home in Shelter Island
4.92 out of 5 average rating, 52 reviewsBeautiful beach home with pool & water views!
Sep. 25 – Oct. 2
Home in East Marion
4.95 out of 5 average rating, 99 reviewsQuiet, Upscale Retreat by the Beach
Dec. 18 – 25
Home in Greenport
5.0 out of 5 average rating, 3 reviewsWaterfront Greenport Boathouse
Dec. 14 – 21
Home in Greenport
5.0 out of 5 average rating, 18 reviewsWalk to Beach or to Town …
Nov. 16 – 23
Home in Greenport
4.99 out of 5 average rating, 84 reviewsGreenport Village Rental
Aug. 11 – 16
Home in Greenport
4.9 out of 5 average rating, 20 reviewsmodern 3 bedroom home with fireplace
Dec. 14 – 21
Home in Southold
5.0 out of 5 average rating, 31 reviewsSalt & Sea House - Near wineries, farms, & beaches
Jun. 3 – 10
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
$164 CAD before taxes and fees
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