Holiday 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.
Holiday 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, 112 reviewsSag Harbor Gem, private, 4 Bedrooms, Pool w Summer
Home in East Hampton
4.87 out of 5 average rating, 188 reviewsHeated Saltwater Pool, Walk to Beach, Dog Friendly
Home in Manorville
4.99 out of 5 average rating, 205 reviewsUltimate House with Heated Pool, Hot Tub and Sauna
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 Cutchogue
5.0 out of 5 average rating, 26 reviewsNorth Fork paradise between beaches and vineyards
Home in Shelter Island
5.0 out of 5 average rating, 16 reviewsFamily Friendly Oasis Steps to Water - Heated Pool
Home in Shelter Island
4.97 out of 5 average rating, 76 reviewsModern, spacious SI home with pool
Apartment rentals with a pool
Apartment in Montauk
4.95 out of 5 average rating, 110 reviewsDeluxe Studio Apt@The Montauk Manor
Apartment in Montauk
4.8 out of 5 average rating, 232 reviewsMontauk Royal Atlantic Beach Resort North
Apartment in Montauk
4.82 out of 5 average rating, 158 reviewsCoastline View Studio
Apartment in Greenport
4.87 out of 5 average rating, 82 reviewsSeaside Escape w Pool, Private Beach & Patio
Apartment in Greenport
5.0 out of 5 average rating, 91 reviews"Breathtaking Waterfront Water's Edge view"
Apartment in Montauk
5.0 out of 5 average rating, 3 reviewsSun N Sound Resort, Montauk, NY
Apartment in Bridgehampton
4.92 out of 5 average rating, 13 reviewsBridgehampton w/ Pool steps to town 3 bd 2.5 Bath
Apartment in Montauk
5.0 out of 5 average rating, 3 reviewsMontauk Retreat - Steps from Beach and Town
Home rentals with a private pool
Home in East Hampton
4.76 out of 5 average rating, 75 reviewsBike to Town and Beach; Saltwater Pool + Cinema
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
4.8 out of 5 average rating, 40 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 holiday 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
€ 157 before taxes and fees
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