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 Hampton Bays
4.77 out of 5 average rating, 97 reviewsJacuzzi & pool. Fenced in property.
Home in East Hampton
4.97 out of 5 average rating, 31 reviewsPretty East Hampton Village Fringe - Hansom Hills
Home in East Hampton
4.88 out of 5 average rating, 17 reviews4 BR/3BA Quiet Pool Home
Home in North Fork
4.94 out of 5 average rating, 33 reviewsBailey House
Home in East Hampton
4.9 out of 5 average rating, 42 reviewsBright Modern Home With Stunning Yard & Pool
Home in East Hampton
4.82 out of 5 average rating, 91 reviewsEast Hampton Oasis - Pool and Hot Tub
Home in Manorville
4.98 out of 5 average rating, 242 reviewsUltimate House with Heated Pool, Hot Tub and Sauna
Home in Rocky Point
4.96 out of 5 average rating, 91 reviewsLuxury modern farmhouse with heated pool & hot tub
Condo rentals with a pool
Condo in Montauk
4.91 out of 5 average rating, 23 reviews1 BR Loft Apt- Montauk Manor- Pools, Tennis & Gym!
Condo in North Fork
4.83 out of 5 average rating, 123 reviewsSeaside Escape w Pool, Private Beach + Patio
Condo in Montauk
5 out of 5 average rating, 209 reviewsMontauk Waterfront Condo w/ Sunset Views
Condo in Montauk
4.89 out of 5 average rating, 9 reviewsEndless Summer Studio Condo w Balcony Bayview
Condo in North Fork
4.88 out of 5 average rating, 147 reviewsBeautiful Waterview Condo on the North Fork of LI
Condo in North Fork
5 out of 5 average rating, 107 reviews"Breathtaking Waterfront Water's Edge view"
Condo in Hampton Bays
4.95 out of 5 average rating, 42 reviewsA Unique Piece of Paradise, Water Front pool
Condo in North Fork
4.92 out of 5 average rating, 137 reviewsBeachside Waterview 2Br Condo w/ Pool in Greenport
Home rentals with a private pool
Home in East Hampton
4.98 out of 5 average rating, 128 reviewsExplore the Water & Woods at a Relaxing Retreat
Home in East Hampton
4.88 out of 5 average rating, 33 reviewsChic Poolside Hideaway in East Hampton
Home in Water Mill
4.92 out of 5 average rating, 120 reviewsBeach Barn w/ Sauna and Heated Pool - Dog Friendly
Home in Southampton
5 out of 5 average rating, 81 reviewsBest of Country and Beach Living
Home in East Hampton
4.82 out of 5 average rating, 45 reviewsEnchanting Home with Large Decks and Heated Pool
Home in Southampton
4.93 out of 5 average rating, 61 reviewsSouthampton Quiet Private Home/Pool 6min to Villag
Home in Southampton
4.95 out of 5 average rating, 20 reviewsPerfect Getaway at Sunny Modern Shampton Lake House
Home in East Hampton
5 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
Nightly prices starting at
$170 before taxes and fees
Total number of reviews
770 reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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