
House vacation rentals in Shelter Island
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Top-rated house rentals in Shelter Island
Guests agree: these houses 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 house rentals
House rentals with a pool

Private Oasis W/Stunning Vinyard and Pool Views

4 BD w/ Heated Pool in E Hampton, Fully Furnished

Spacious Home with Pool in Southold

Gorgeous home with saltwater pool. Steps to beach!

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna

Amazing Home in SH with private heated Pool

1800 Historical East Hampton Home, 1 Mile to Town!

Ultimate House with Heated Pool, Hot Tub and Sauna
Weekly house rentals

Private Waterfront Access + Hot Tub + Scenic Yard

Beach Cottage | Steps to Water| Fireplace|Firepit

Salt & Sea House - Near wineries, farms, & beaches

The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub

Hamptons Oceanfront Oasis

Renovated Southampton Home+Pool

Le Petit Cottage, Southold, NY

Cottage by the beach
Private house rentals

Adorable Beach House on LI Sound

Greenport Getaway - North Fork Rental

Waterfront Beach House Gardens, AC, BBQ, Kyaks

North Fork Farmhouse with Saltwater Pool

Mulberry Seaside Cottage

The Olde Church in Greenport

Summer Getaway in the Hamptons. Mins from Beaches

Walk to town, Greenport Village - Harbor Views
Quick stats about house rentals in Shelter Island
Total rentals
110 properties
Nightly prices starting at
R177 ZAR before taxes and fees
Total number of reviews
1.9K reviews
Family-friendly rentals
100 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
50 properties have a pool
Destinations to explore
- The Hamptons Vacation rentals
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- Rentals with outdoor seating Shelter Island
- Kid-friendly rentals Shelter Island
- Rentals with pools Shelter Island
- Family-friendly rentals Shelter Island
- Rentals with a kayak Shelter Island
- Rentals with a fire pit Shelter Island
- Waterfront rentals Shelter Island
- Rentals with a fireplace Shelter Island
- Rentals with a patio Shelter Island
- Pet-friendly rentals Shelter Island
- Rentals with a hot tub Shelter Island
- Fitness-friendly rentals Shelter Island
- Rentals with a washer and dryer Shelter Island
- Rentals with beach access Shelter Island
- Beachfront rentals Shelter Island
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- Beach
- Charlestown Beach
- Fairfield Beach
- Yale University
- Southampton Beach
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- Napeague Beach
- TPC River Highlands
- Ocean Beach Park
- Shinnecock Hills Golf Club
- Walnut Public Beach
- Woodmont Beach
- Jennings Beach
- Blue Shutters Beach
- Ninigret Beach
- Silver Sands Beach
- Amagansett Beach
- Groton Long Point Main Beach
- Sunken Meadow State Park
- Seaside Beach
- South Jamesport Beach
- Sandy Beach
- Brownstone Adventure Sports Park