Shelter Island Summer Rentals, Cottages & Cabins

Book a Place to Stay in Shelter Island for Your Summer Getaway

About Shelter Island Summer Rental on SunSkiResorts

SunSki's selection of summer rentals in Shelter Island promises the ideal setting for your next seasonal escape. We offer a diverse array of properties boasting enticing features such as private pools, indoor/outdoor swimming facilities, hot tubs, WiFi, beachfront access, and more. Whether you're journeying with family, friends, or a larger group, we have a rental perfectly tailored to your requirements.

Immerse yourself in the epitome of summer leisure in Shelter Island with SunSki. Our summer rental accommodations are meticulously curated to ensure utmost comfort and relaxation. From chic condos and opulent resorts to charming villas, quaint bungalows, cozy cabins, RVs, and cottages, we present a spectrum of options to match your vacation vision. Discover your idyllic summer retreat with SunSki.

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Frequently Asked Questions About Shelter Island Luxury Rentals

There are a lot of options in Shelter Island. If you plan on staying in the Shelter Island area, consider making a reservation for a few nights at one of these properties as these have been rated the top Summer Rentals in Shelter Island:

In 2025, SunSki offers 1273 summer rentals in or around Shelter Island. Find unique home rentals for your summer holiday or a weekend getaway with family and friends.
The average price per night for a summer rental in Shelter Island is $453. Check the full list of summer accommodations in Shelter Island.
There are 1273 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with SunSkiResorts.

Yes, here are some popular summer holiday rentals in Shelter Island that have a private or indoor pool:

Check all holiday rentals with a pool in Shelter Island on SunSkiResorts.

Yes, We have 1273 summer rental homes in Shelter Island and types of place to stay in Shelter Island include:

  • Vacation Homes: 1273 available for rent
  • Villas: 1273 Rentals available for rent
  • Holiday Apartments: 1273 Rentals available for rent
  • Hotels with Suites: 1273 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Shelter Island. Use our search filter to discover all of our luxury summer accommodations with an indoor/outdoor pool. Sorting by price is another way to find the most and least expensive luxury summer rentals in Shelter Island.