Search Shelter Island Vacation Rentals

Rental Period:	Any Time Period Week Month Year June July July - Labor Day Memorial Day - Labor Day August - Labor Day August Extended Season Sept. October
Maximum Price:	-- $10,000 $25,000 $50,000 $75,000 $100,000 +
Min. Bedrooms:	-- N/A 1 2 3 4 5 6+
Min. Bathrooms:	-- N/A 1 2 3 4 5 6+
Pool:		Tennis:
Waterfront:		Waterview:
Dock:

 

An Ideal Way to Enjoy a Stay on Scenic Shelter Island

Shelter Island’s renowned location 100 miles outside of New York City has it all -- tennis in the Heights and Moussa Drame Tennis Academy at the Pridwin; Hampshire Farms Stables; Heights Beach Club; Golf at Gardiners Bay Country Club or Shelter Island Golf Club; Junior Sailing at the Shelter Island yacht Club; Shelter Island Yoga & Fitness at the Dering Harbor Inn; Shelter Island Fit Center & Yoga and Barr classes in the Center

Charming Year Round & Seasonal Getaways

We offer Shelter Island rentals to suit all occasions, including:

• Seasonal, Monthly & Yr. Round
• Waterfront rentals, water view rentals and rentals with pools
• All styles of Shelter Island rentals, from secluded compounds to rustic cottages
• Shelter Island summer rentals with all the amenities you need including pools and fully furnished kitchens, beds and baths