Holiday 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.
Holiday 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 Cutchogue
4.87 out of 5 average rating, 116 reviewsThe Perfect North Fork Escape
13–20 Oct
Home in Cutchogue
4.96 out of 5 average rating, 190 reviewsStunning Vinyard Views - Spring Special $475/Nt!
29 Oct – 5 Nov
Home in East Hampton
4.88 out of 5 average rating, 101 reviewsGorgeous East Hampton Getaway
19–26 Nov
Home in Shelter Island
5.0 out of 5 average rating, 50 reviewsCASA GYPSEA - a chic and peaceful 3 bedroom house
13–20 Nov
Home in Shelter Island
4.92 out of 5 average rating, 52 reviewsBeautiful beach home with pool & water views!
10–17 Nov
Home in Southold
5.0 out of 5 average rating, 10 reviewsGorgeous home with heated gunnite pool!
1–8 Apr
Home in Shelter Island
5.0 out of 5 average rating, 10 reviewsSpacious house with pool.
10–17 Jul
Home in Shelter Island
4.97 out of 5 average rating, 76 reviewsModern, spacious SI home with pool
18–25 Jan
Apartment rentals with a pool
Apartment in Montauk
4.99 out of 5 average rating, 181 reviewsMontauk Waterfront Condo w/ Sunset Views
5–12 Mar
Apartment in Montauk
4.95 out of 5 average rating, 107 reviewsDeluxe Studio Apt@The Montauk Manor
23–30 Apr
Apartment in Montauk
4.8 out of 5 average rating, 232 reviewsMontauk Royal Atlantic Beach Resort North
15–22 Aug
Apartment in Montauk
4.82 out of 5 average rating, 158 reviewsCoastline View Studio
31 Oct – 7 Nov
Apartment in Greenport
5.0 out of 5 average rating, 90 reviews"Breathtaking Waterfront Water's Edge view"
27 Sep – 4 Oct
Apartment in Greenport
4.89 out of 5 average rating, 81 reviewsSeaside Escape w Pool, Private Beach & Patio
22–29 Jan
Apartment in Bridgehampton
4.92 out of 5 average rating, 13 reviewsBridgehampton w/ Pool steps to town 3 bd 2.5 Bath
2–9 Dec
Apartment in Montauk
4.74 out of 5 average rating, 39 reviewsThe Exclusive Resort in Montauk
3–10 Nov
Home rentals with a private pool
Home in Water Mill
4.91 out of 5 average rating, 110 reviewsBeach Barn w/ Sauna and Heated Pool - Dog Friendly
1–8 Jan
Home in East Hampton
4.94 out of 5 average rating, 16 reviewsWalk to Water. Stunning Home with Gorgeous Pool & Grounds.
18–25 Sep
Home in Remsenburg
4.95 out of 5 average rating, 64 reviewsExperience a Quiet Hamptons Getaway
30 Jan – 6 Feb
Home in Southampton
4.94 out of 5 average rating, 16 reviewsPerfect Getaway at Sunny Modern Shampton Lake House
1–8 Jan
Home in East Hampton
5.0 out of 5 average rating, 13 reviewsSaltbox with Separate Poolhouse in Northwest Woods
3–10 Apr
Home in East Hampton
4.79 out of 5 average rating, 39 reviewsEnchanting Home with Large Decks and Heated Pool
24–31 Dec
Bungalow in East Hampton
4.93 out of 5 average rating, 99 reviewsEast Hampton Ranch with Access to Clearwater Private Beach
4–11 May
Quick stats about holiday 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
€ 121 before taxes and fees
Destinations to explore
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