
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

Breathtaking Sag Harbor 5 bed 6 bath-Heated Pool

Gorgeous home with saltwater pool. Steps to beach!

Perfect Beach Home in Sag Harbor

Classic Southampton Village Home w/ Pool

Modern farmhouse w/ pool, beach, horses and winery

CASA GYPSEA - a chic and peaceful 3 bedroom house

Modern House close to the beach

Fully renovated dream summer house in the Hamptons
Condo rentals with a pool

Second Floor Corner Unit Overlooking the Ocean

Beautiful condo on Long Islands Northfork

Montauk Waterfront Condo w/ Sunset Views

Endless Summer Studio Condo w Balcony Bayview

Waterfront Elevated Bungalow - Spectacular Views

Waterfront Autumn Escape in Wine Country: 2BR

Beachside Waterview 2Br Condo w/ Pool in Greenport

Waterfront Condo C-204 at The Cliffside Resort
Home rentals with a private pool

East Hampton Ranch with Access to Clearwater Private Beach

Explore the Water & Woods at a Relaxing Retreat

Beach Barn w/ Heated Pool & Sauna - Dog Friendly
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 Heights
Total rentals
150 properties
Nightly prices starting at
€ 147 before taxes and fees
Total number of reviews
3.7K reviews
Family-friendly rentals
140 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
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- Rentals with outdoor seating Shelter Island Heights
- Rentals with a fireplace Shelter Island Heights
- Rentals with breakfast Shelter Island Heights
- Beachfront rentals Shelter Island Heights
- Rentals with a washer and dryer Shelter Island Heights
- Apartment rentals Shelter Island Heights
- Rentals with beach access Shelter Island Heights
- Cottage rentals Shelter Island Heights
- Family-friendly rentals Shelter Island Heights
- Condo rentals Shelter Island Heights
- Rentals with a hot tub Shelter Island Heights
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- House rentals Shelter Island Heights
- Boutique hotel rentals Shelter Island Heights
- Fitness-friendly rentals Shelter Island Heights
- Rentals with a kayak Shelter Island Heights
- Rentals with a fire pit Shelter Island Heights
- Pet-friendly rentals Shelter Island Heights
- Waterfront rentals Shelter Island Heights
- 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