146+ Private Villas and Holiday Rentals in Shelter Island |
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Shelter Island Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Shelter Island

Discover more than 146 vacation rentals available in Shelter Island. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Shelter Island.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Shelter Island, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Shelter Island. On average, places to stay near Shelter Island offer 892.96 ft², with nightly prices averaging ZA R18,613.

With Casai, finding and comparing holiday rentals in Shelter Island is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Shelter Island

Type Count
Vacation Homes 126
Holiday Apartments 4
Cottages 3

Use these Quick Filters to Find a Holiday Rental in Shelter Island

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Shelter Island.

Weather in Shelter Island, NY

View the weather forecast for Shelter Island before booking your Shelter Island Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Shelter Island, NY

Casai offers a large selection of top attractions around Shelter Island . Research things to do on your vacation before you visit Shelter Island.


Mashomack Preserve
Shelter Island Kayak
Wades Beach
Sylvester Manor
Havens House
Shelter Island Historical Society
Cooper's Beach
East Hampton Main Beach
Wolffer Estates Vineyard
Hammonasset Beach State Park
Meschutt Beach
Guild Hall
Ditch Plains Beach
Hither Hills State Park
Clinton Crossing Premium Outlets
The Hamptons Beaches
Orient Beach State Park
Bay Street Theatre
Indian Wells Beach
Ponquogue Beach

Other Places to Stay in Shelter Island, NY


Sylvester Manor 363 Properties
Shelter Island Kayak 305 Properties
Shelter Island Historical Society 222 Properties
Havens House 219 Properties
Menantic Creek 213 Properties
Shorewood 182 Properties
Wades Beach 178 Properties
Mashomack Preserve 174 Properties
Shelter Island Heights 97 Properties

Frequently Asked Questions About Shelter Island?

What are the top holiday rentals in Shelter Island?

With numerous options available in Shelter Island, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Shelter Island:

How many holiday rentals have private pools in Shelter Island?

Discover a selection of holiday rentals with private pools near Shelter Island with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Shelter Island are best for families?

If you're searching for a family-friendly holiday home in Shelter Island, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Shelter Island:

How many Casai.co.za holiday rentals are available in Shelter Island?

As of 2025, Casai boasts over 146 properties listed in the Shelter Island area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Shelter Island.

Nearby Neighborhood (5) 
Neighborhood Property Count
The Heights Vacation Rentals in Shelter Island, New York 419
Menantic Creek Vacation Rentals in Shelter Island, New York 213
Coecles Harbor Vacation Rentals in Shelter Island, New York 293
Shorewood Vacation Rentals in Shelter Island, New York 182
Montclair Colony Vacation Rentals in Shelter Island, New York 197

People Also Ask

There are 146 Shelter Island, NY Holiday Rentals

Recently Booked Holiday Rentals in Shelter Island