Vacation rentals with a pool in Shelter Island
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Shelter Island
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 rentals with a pool
House rentals with a pool
Home in Cutchogue
4.96 out of 5 average rating, 190 reviewsStunning Vinyard Views - Spring Special $475/Nt!
Apr 6 – 13
Home in Shelter Island
5.0 out of 5 average rating, 50 reviewsCASA GYPSEA - a chic and peaceful 3 bedroom house
Jan 21 – 28
Home in Shelter Island
4.92 out of 5 average rating, 52 reviewsBeautiful beach home with pool & water views!
Dec 27 – Jan 3
Home in Shelter Island
5.0 out of 5 average rating, 10 reviewsSpacious house with pool.
Nov 1 – 8
Home in Shelter Island
5.0 out of 5 average rating, 16 reviewsFamily Friendly Oasis Steps to Water - Heated Pool
Jan 9 – 16
Home in Sag Harbor
4.98 out of 5 average rating, 88 reviewsPerfection in Sag Harbor 5 Br 1 block from water
Apr 2 – 9
Home in Shelter Island
4.97 out of 5 average rating, 76 reviewsModern, spacious SI home with pool
Jan 26 – Feb 2
Home in Cutchogue
5.0 out of 5 average rating, 24 reviewsNorth Fork paradise between beaches and vineyards
Nov 7 – 14
Condo rentals with a pool
Condo in Montauk
4.99 out of 5 average rating, 181 reviewsMontauk Waterfront Condo w/ Sunset Views
Feb 6 – 13
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 15 – 22
Condo in Montauk
4.82 out of 5 average rating, 158 reviewsCoastline View Studio
Oct 30 – Nov 6
Condo in Greenport
4.89 out of 5 average rating, 81 reviewsSeaside Escape w Pool, Private Beach & Patio
Dec 4 – 11
Condo in Greenport
5.0 out of 5 average rating, 90 reviews"Breathtaking Waterfront Water's Edge view"
Sep 26 – Oct 3
Condo in Montauk
4.74 out of 5 average rating, 39 reviewsThe Exclusive Resort in Montauk
Nov 3 – 10
Condo in Montauk
4.82 out of 5 average rating, 87 reviewsBeautiful Condo on the Ocean Bluffs
Nov 19 – 26
Home rentals with a private pool
Home in Remsenburg
4.95 out of 5 average rating, 64 reviewsExperience a Quiet Hamptons Getaway
Jan 29 – Feb 5
Home in Southampton
4.94 out of 5 average rating, 16 reviewsPerfect Getaway at Sunny Modern Shampton Lake House
Jan 1 – 8
Home in East Hampton
5.0 out of 5 average rating, 13 reviewsSaltbox with Separate Poolhouse in Northwest Woods
Apr 2 – 9
Home in East Hampton
4.79 out of 5 average rating, 39 reviewsEnchanting Home with Large Decks and Heated Pool
Feb 17 – 24
Bungalow in East Hampton
4.93 out of 5 average rating, 99 reviewsEast Hampton Ranch with Access to Clearwater Private Beach
May 4 – 11
Quick stats about vacation rentals with a pool in Shelter Island
Total rentals
50 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
720 reviews
Nightly prices starting at
$170 before taxes and fees
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