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 Sag Harbor
4.81 out of 5 average rating, 109 reviewsSag Harbor Gem, private, 4 Bedrooms, Pool w Summer
Jun 6 – 13
Home in Cutchogue
4.96 out of 5 average rating, 190 reviewsStunning Vinyard Views - Spring Special $475/Nt!
Feb 4 – 11
Home in Manorville
4.98 out of 5 average rating, 199 reviewsUltimate House with Heated Pool, Hot Tub and Sauna
Oct 2 – 9
Home in Shelter Island
5.0 out of 5 average rating, 50 reviewsCASA GYPSEA - a chic and peaceful 3 bedroom house
Dec 29 – Jan 5
Home in Shelter Island
5.0 out of 5 average rating, 10 reviewsSpacious house with pool.
Oct 28 – Nov 4
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 Shelter Island
5.0 out of 5 average rating, 16 reviewsFamily Friendly Oasis Steps to Water - Heated Pool
Mar 21 – 28
Home in Shelter Island
4.97 out of 5 average rating, 76 reviewsModern, spacious SI home with pool
Mar 12 – 19
Condo rentals with a pool
Condo in Montauk
4.95 out of 5 average rating, 107 reviewsDeluxe Studio Apt@The Montauk Manor
Mar 30 – Apr 6
Condo in Montauk
4.99 out of 5 average rating, 181 reviewsMontauk Waterfront Condo w/ Sunset Views
Sep 13 – 20
Condo in Montauk
4.8 out of 5 average rating, 232 reviewsMontauk Royal Atlantic Beach Resort North
Jul 20 – 27
Condo in Montauk
4.82 out of 5 average rating, 158 reviewsCoastline View Studio
Oct 26 – Nov 2
Condo in Greenport
5.0 out of 5 average rating, 90 reviews"Breathtaking Waterfront Water's Edge view"
Jan 5 – 12
Condo in Greenport
4.89 out of 5 average rating, 80 reviewsSeaside Escape w Pool, Private Beach & Patio
Apr 8 – 15
Condo in Montauk
4.74 out of 5 average rating, 39 reviewsThe Exclusive Resort in Montauk
Apr 19 – 26
Condo in Montauk
4.82 out of 5 average rating, 87 reviewsBeautiful Condo on the Ocean Bluffs
Mar 27 – Apr 3
Home rentals with a private pool
Home in Remsenburg
4.95 out of 5 average rating, 64 reviewsExperience a Quiet Hamptons Getaway
Jan 24 – 31
Home in Southampton
4.94 out of 5 average rating, 16 reviewsPerfect Getaway at Sunny Modern Shampton Lake House
Jan 14 – 21
Home in East Hampton
5.0 out of 5 average rating, 13 reviewsSaltbox with Separate Poolhouse in Northwest Woods
Apr 4 – 11
Home in East Hampton
4.79 out of 5 average rating, 39 reviewsEnchanting Home with Large Decks and Heated Pool
Apr 2 – 9
Bungalow in East Hampton
4.93 out of 5 average rating, 99 reviewsEast Hampton Ranch with Access to Clearwater Private Beach
May 21 – 28
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
€ 159 before taxes and fees
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