Vacation rentals with a pool in Shelter Island Heights
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Shelter Island Heights
Guests agree: these homes with a pool 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 rentals with a pool
House rentals with a pool
Home in Cutchogue
4.87 out of 5 average rating, 116 reviewsThe Perfect North Fork Escape
Oct 15 – 22
Home in Cutchogue
4.96 out of 5 average rating, 190 reviewsStunning Vinyard Views - Spring Special $475/Nt!
Dec 31 – Jan 7
Home in Sag Harbor
4.82 out of 5 average rating, 132 reviewsNew! Sag Harbor Village Pool, Hot Tub &Beach House
Nov 7 – 14
Home in Shelter Island
5.0 out of 5 average rating, 50 reviewsCASA GYPSEA - a chic and peaceful 3 bedroom house
Apr 15 – 22
Home in Greenport
5.0 out of 5 average rating, 19 reviewsThe Corwin House
May 9 – 16
Home in Shelter Island
4.92 out of 5 average rating, 52 reviewsBeautiful beach home with pool & water views!
May 10 – 17
Home in Shelter Island
4.97 out of 5 average rating, 76 reviewsModern, spacious SI home with pool
Dec 9 – 16
Home in Southold
5.0 out of 5 average rating, 10 reviewsGorgeous home with heated gunnite pool!
Mar 15 – 22
Condo rentals with a pool
Condo in Montauk
4.99 out of 5 average rating, 181 reviewsMontauk Waterfront Condo w/ Sunset Views
Apr 2 – 9
Condo in Montauk
4.95 out of 5 average rating, 107 reviewsDeluxe Studio Apt@The Montauk Manor
Apr 23 – 30
Condo in Montauk
4.8 out of 5 average rating, 232 reviewsMontauk Royal Atlantic Beach Resort North
Aug 1 – 8
Condo in Montauk
4.82 out of 5 average rating, 158 reviewsCoastline View Studio
Apr 12 – 19
Condo in Greenport
4.83 out of 5 average rating, 100 reviewsSeaside Escape w Pool, Private Beach + Patio
Jan 12 – 19
Condo in Greenport
5.0 out of 5 average rating, 90 reviews"Breathtaking Waterfront Water's Edge view"
Sep 29 – Oct 6
Condo in Bridgehampton
4.92 out of 5 average rating, 13 reviewsBridgehampton w/ Pool steps to town 3 bd 2.5 Bath
Dec 2 – 9
Condo in Montauk
4.82 out of 5 average rating, 87 reviewsBeautiful Condo on the Ocean Bluffs
Oct 21 – 28
Home rentals with a private pool
Home in Water Mill
4.91 out of 5 average rating, 110 reviewsBeach Barn w/ Sauna and Heated Pool - Dog Friendly
Nov 11 – 18
Home in Remsenburg
4.95 out of 5 average rating, 64 reviewsExperience a Quiet Hamptons Getaway
Feb 1 – 8
Home in Southampton
4.94 out of 5 average rating, 16 reviewsPerfect Getaway at Sunny Modern Shampton Lake House
Jan 13 – 20
Home in East Hampton
5.0 out of 5 average rating, 13 reviewsSaltbox with Separate Poolhouse in Northwest Woods
Apr 5 – 12
Home in East Hampton
4.79 out of 5 average rating, 39 reviewsEnchanting Home with Large Decks and Heated Pool
Sep 23 – 30
Bungalow in East Hampton
4.93 out of 5 average rating, 99 reviewsEast Hampton Ranch with Access to Clearwater Private Beach
May 7 – 14
Quick stats about vacation rentals with a pool in Shelter Island Heights
Total rentals
100 properties
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
80 properties are a good fit for families
Total number of reviews
1.6K reviews
Nightly prices starting at
ﺩ.ﺇ477 before taxes and fees
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