
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

Private Oasis W/Stunning Vinyard and Pool Views

Designer Chic Home w/ Heated Gunite Saltwater Pool

Spectacular Southampton Retreat!

Breathtaking Sag Harbor 5 bed 6 bath-Heated Pool

Gorgeous home with saltwater pool. Steps to beach!

North Fork Sound Front Home with Pool

CASA GYPSEA - a chic and peaceful 3 bedroom house

Cedar Cottage with Fab Pool on Shelter Island, NY
Apartment rentals with a pool

Second Floor Corner Unit Overlooking the Ocean

1 BR Loft Apt- Montauk Manor- Pools, Tennis & Gym!

Montauk Waterfront Condo w/ Sunset Views

Endless Summer Studio Condo w Balcony Bayview

Beautiful Waterview Condo on the North Fork of LI

1856 Trading House close to water

Deluxe Studio Apt@The Montauk Manor

Montauk Oceanfront Condo
Home rentals with a private pool

Explore the Water & Woods at a Relaxing Retreat
East Hampton Ranch with Access to Clearwater Private Beach

Chic Poolside Hideaway in East Hampton
Enchanting Home with Large Decks and Heated Pool
Perfect Getaway at Sunny Modern Shampton Lake House
Saltbox with Separate Poolhouse in Northwest Woods
Quick stats about holiday rentals with a pool in Shelter Island Heights
Total rentals
160 properties
Nightly prices starting at
£126 before taxes and fees
Total number of reviews
3.5K reviews
Family-friendly rentals
130 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with dedicated workspaces
80 properties have a dedicated workspace
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
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- Boston Holiday rentals
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- East River Holiday rentals
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- Mount Pocono Holiday rentals
- The Hamptons Holiday rentals
- Rentals with breakfast Shelter Island Heights
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- Rentals with a hot tub Shelter Island Heights
- Boutique hotel rentals Shelter Island Heights
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- Rentals with pools Suffolk County
- Rentals with pools New York
- Rentals with pools United States
- Yale University
- Charlestown Beach
- Fairfield Beach
- Foxwoods Resort Casino
- Southampton Beach
- Cooper's Beach, Southampton
- Ocean Beach Park
- Walnut Public Beach
- Napeague Beach
- Shinnecock Hills Golf Club
- Blue Shutters Beach
- TPC River Highlands
- Brownstone Adventure Sports Park
- Woodmont Beach
- Jennings Beach
- Silver Sands Beach
- Cedar Beach
- Sandy Beach
- Groton Long Point Main Beach
- Ninigret Beach
- Sunken Meadow State Park
- Seaside Beach
- Wildemere Beach
- Harveys Beach