
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

Southold Home with Saltwater Pool (until 10/13)

East Hampton 3 Bed / 3 Bath Charmer w Pool

Modern East Hampton Home w/ Heated Saltwater Pool

Stylish+Modern Cape w/Saltwater Pool-5min to Beach

Perfect Beach Home in Sag Harbor

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna

Luxury Beach House | Pool & Hot Tub | Sag Harbor

5BR/4BA: Sag Harbor, Pool, Fireplace, Near to town
Condo rentals with a pool

Beautiful condo on Long Islands Northfork

2 BR Waterfront Autumn Escape in Wine Country

Waterfront Elevated Bungalow - Spectacular Views

Beautiful Waterview Condo on the North Fork of LI

Bridgehampton w/ Pool steps to town 3 bd 2.5 Bath

Newly Renovated Modern Townhouse w/Pool & Tennis

A Unique Piece of Paradise, Water Front pool

Waterfront Autumn Escape in Wine Country: 2BR
Home rentals with a private pool

East Hampton Ranch with Access to Clearwater Private Beach
Enchanting Home with Large Decks and Heated Pool

Southampton Quiet Private Home/Pool 6min to Villag
Perfect Holiday Getaway with Gourmet Kitchen
Saltbox with Separate Poolhouse in Northwest Woods
Quick stats about vacation rentals with a pool in Shelter Island
Total rentals
60 properties
Nightly prices starting at
€ 146 before taxes and fees
Total number of reviews
1K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Destinations to explore
- Plainview Vacation rentals
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- Family-friendly rentals Shelter Island
- Pet-friendly rentals Shelter Island
- Rentals with a fire pit Shelter Island
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- Rentals with outdoor seating Shelter Island
- Rentals with a kayak Shelter Island
- Rentals with a hot tub Shelter Island
- House rentals Shelter Island
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- Fitness-friendly rentals Shelter Island
- Rentals with a patio Shelter Island
- Rentals with beach access Shelter Island
- Rentals with a washer and dryer Shelter Island
- Rentals with pools Suffolk County
- Rentals with pools New York
- Rentals with pools United States
- Yale University
- Foxwoods Resort Casino
- Charlestown Beach
- Fairfield Beach
- Southampton Beach
- Cooper's Beach, Southampton
- Ocean Beach Park
- Walnut Public Beach
- Blue Shutters Beach
- Shinnecock Hills Golf Club
- Napeague Beach
- Cedar Beach
- Groton Long Point Main Beach
- TPC River Highlands
- Brownstone Adventure Sports Park
- Woodmont Beach
- Silver Sands Beach
- Sunken Meadow State Park
- Sandy Beach
- Jennings Beach
- Wildemere Beach
- Ninigret Beach
- Mystic Seaport Museum
- Outer Beach at Smith Point County Park