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 Shelter Island
4.92 out of 5 average rating, 52 reviewsBeautiful beach home with pool & water views!
Home in Shelter Island
5.0 out of 5 average rating, 51 reviewsCASA GYPSEA - a chic and peaceful 3 bedroom house
Home in Shelter Island
4.97 out of 5 average rating, 76 reviewsModern, spacious SI home with pool
Home in Shelter Island
5.0 out of 5 average rating, 16 reviewsFamily Friendly Oasis Steps to Water - Heated Pool
Home in Shelter Island
5.0 out of 5 average rating, 10 reviewsSpacious house with pool.
Home in Cutchogue
5.0 out of 5 average rating, 26 reviewsNorth Fork paradise between beaches and vineyards
Home in East Hampton
4.86 out of 5 average rating, 77 reviews4 BD w/ Heated Pool in E Hampton, Fully Furnished
Home in Sag Harbor
5.0 out of 5 average rating, 27 reviewsSag Harbor Modern Oasis
Condo rentals with a pool
Condo in Montauk
4.94 out of 5 average rating, 109 reviewsDeluxe Studio Apt@The Montauk Manor
Condo in Montauk
4.8 out of 5 average rating, 232 reviewsMontauk Royal Atlantic Beach Resort North
Condo in Montauk
4.82 out of 5 average rating, 158 reviewsCoastline View Studio
Condo in Greenport
4.83 out of 5 average rating, 100 reviewsSeaside Escape w Pool, Private Beach + Patio
Condo in Greenport
5.0 out of 5 average rating, 91 reviews"Breathtaking Waterfront Water's Edge view"
Condo in Bridgehampton
4.92 out of 5 average rating, 13 reviewsBridgehampton w/ Pool steps to town 3 bd 2.5 Bath
Condo in Montauk
5.0 out of 5 average rating, 3 reviewsMontauk Retreat - Steps from Beach and Town
Condo in Montauk
4.81 out of 5 average rating, 26 reviewsMontauk Sunsets
Home rentals with a private pool
Home in Remsenburg
4.95 out of 5 average rating, 64 reviewsExperience a Quiet Hamptons Getaway
Home in Southampton
4.94 out of 5 average rating, 16 reviewsPerfect Getaway at Sunny Modern Shampton Lake House
Home in East Hampton
4.79 out of 5 average rating, 39 reviewsEnchanting Home with Large Decks and Heated Pool
Home in East Hampton
5.0 out of 5 average rating, 13 reviewsSaltbox with Separate Poolhouse in Northwest Woods
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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