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 Sag Harbor
4.81 out of 5 average rating, 108 reviewsSag Harbor Gem, private, 4 Bedrooms, Pool w Summer
Jun. 6 – 13
Home in Cutchogue
4.87 out of 5 average rating, 115 reviewsThe Perfect North Fork Escape
Oct. 4 – 11
Home in Cutchogue
4.96 out of 5 average rating, 190 reviewsStunning Vinyard Views - Spring Special $475/Nt!
Feb. 4 – 11
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 Greenport
5.0 out of 5 average rating, 19 reviewsThe Corwin House
May 16 – 23
Home in Shelter Island
5.0 out of 5 average rating, 10 reviewsSpacious house with pool.
Oct. 27 – Nov. 3
Home in Southold
5.0 out of 5 average rating, 10 reviewsGorgeous home with heated gunnite pool!
Apr. 14 – 21
Home in Shelter Island
4.97 out of 5 average rating, 76 reviewsModern, spacious SI home with pool
Feb. 28 – Mar. 7
Condo rentals with a pool
Condo in Montauk
4.99 out of 5 average rating, 181 reviewsMontauk Waterfront Condo w/ Sunset Views
Mar. 24 – 31
Condo in Montauk
4.95 out of 5 average rating, 107 reviewsDeluxe Studio Apt@The Montauk Manor
Apr. 12 – 19
Condo in Montauk
4.8 out of 5 average rating, 231 reviewsMontauk Royal Atlantic Beach Resort North
Jul. 20 – 27
Condo in Montauk
4.82 out of 5 average rating, 158 reviewsCoastline View Studio
Oct. 25 – Nov. 1
Condo in Greenport
4.89 out of 5 average rating, 80 reviewsSeaside Escape w Pool, Private Beach & Patio
Sep. 28 – Oct. 5
Condo in Greenport
5.0 out of 5 average rating, 90 reviews"Breathtaking Waterfront Water's Edge view"
Jan. 5 – 12
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. 26 – Apr. 2
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
Jan. 25 – Feb. 1
Bungalow in East Hampton
4.93 out of 5 average rating, 99 reviewsEast Hampton Ranch with Access to Clearwater Private Beach
May 2 – 9
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
$178 CAD before taxes and fees
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