
House vacation rentals in Shelter Island
Find and book unique houses on Airbnb
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

Corwin House

Private Oasis W/Stunning Vinyard and Pool Views

Beach Barn w/ Heated Pool & Sauna - Dog Friendly

Modern East Hampton Home w/ Heated Saltwater Pool

Stylish+Cozy Hamptons Winter Getaway-5min to Beach

Chic East Hampton 7 Bedroom, 7 Bath, heated Pool

Classic Southampton Village Home w/ Pool

Astounding Watermill 5 Bedroom home with Pool
Weekly house rentals

Beach Cottage | Steps to Water| Fireplace|Firepit

Spectacular Southampton Retreat!

Gorgeous home with saltwater pool. Steps to beach!

The Sandy Shack - Coastal Escape

Stylish Getaway in Greenport

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

Secluded Luxury: New Gunite Pool, Walk to Bay

The Olde Church in Greenport
Private house rentals

Greenport Getaway - North Fork Rental

Country Beach Home!

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna

Lakehouse Getaway North Fork

Luxury Beach House | Pool & Hot Tub | Sag Harbor

Chic & Spacious Designer Home, Heated Pool/Spa

Coastal Cottage on the Water

Le Petit Cottage, Southold, NY
Quick stats about house rentals in Shelter Island
Total rentals
110 properties
Nightly prices starting at
€ 9 before taxes and fees
Total number of reviews
2.2K 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
- Plainview Vacation rentals
- New York Vacation rentals
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- East River Vacation rentals
- Hudson Valley Vacation rentals
- Philadelphia Vacation rentals
- Mount Pocono Vacation rentals
- Jersey Shore Vacation rentals
- Ocean City Vacation rentals
- The Hamptons Vacation rentals
- Family-friendly rentals Shelter Island
- Rentals with a hot tub Shelter Island
- Rentals with a fireplace Shelter Island
- Beachfront rentals Shelter Island
- Rentals with beach access Shelter Island
- Rentals with a kayak Shelter Island
- Rentals with pools Shelter Island
- Rentals with a fire pit Shelter Island
- Pet-friendly rentals Shelter Island
- Rentals with outdoor seating Shelter Island
- Waterfront rentals Shelter Island
- Rentals with a patio Shelter Island
- Rentals with a washer and dryer Shelter Island
- Fitness-friendly rentals Shelter Island
- House rentals Suffolk County
- House rentals New York
- House rentals 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