Rental Listings
Shelter Island Modern and Clean Close to Beach
Priced at June ('19 - '19) $10,000 Beds: 3 Baths: 2 Sq. Feet: 2708This stylish ranch home, within close proximity to Sunset Beach, golf and fine dining, has been ... Property Details
Dering Harbor Waterfront with Dock and Pool
Priced at MD-LD ('19 - 09/02/19) $125,000; August(LD) ('19 - 19) $65,000 Beds: 4 Baths: 3.5 Sq. Feet: 2300This traditional on a slight hill has incredible sunset views onto Dering Harbor, recently ... Property Details
Shelter Island Contemporary with Pool
Priced at July ('19 - '19*8K for 2 wks.) $16,000; August(LD) ('19 - '19*10K for 2 wks) $20,000 Beds: 4 Baths: 3 Sq. Feet: 2303A four-bedroom, three-bath Contemporary on .50+/- acres in the heart of Shelter Island. The property ... Property Details
Charming 1920’s Waterfront Cottage with Dock
Priced at Two Weeks (07/01/19 - 07/31/19) $4,970; Weekly (08/01/19 - 08/31/19) $5,530 Beds: 1 Baths: 2 Sq. Feet: 875Located within short distance to the ferry, Heights and beach, this tastefully decorated 1920's ... Property Details
South Shore Shelter Island Beauty
Priced at August ('19 - 19**Aug only) $60,000 Beds: 4 Baths: 3.5 Sq. Feet: 3964This restored Victorian carriage house occupies one of the most beautiful and scenic spots on ... Property Details
Sweet Shelter Island Creek Front Bungalow
Priced at June ('19 - 19) $2,000 RENTED; July ('19 - 19) $4,500 RENTED; August(LD) ('19 - 19) $6,000 RENTED Beds: 1 Baths: 1 Sq. Feet: 400This quaint one bedroom, one bath studio cottage is located in estate section and offers southerly ... Property Details
Pristine Shelter Island Bay View with Dock Access
Priced at June ('19 - 19) $12,000; July ('19 - '19) $14,000; Ext. Season (09/01/19 - 09/30/19 same 4 Oct) $8,000 Beds: 2 Baths: 1 Bath, 1 Half Sq. Feet: 1608This recently renovated ranch has a sunny living room, kitchen with new appliances and two bedrooms, ... Property Details
Classic and Chic
Priced at June ('19 - '19) $12,000 RENTED; July ('19 - '19) $14,000 RENTED; August(LD) ('19 - '19) $16,000 RENTED Beds: 4 Baths: 3 Sq. Feet: 2618Newly renovated house with an interesting mix of old world furnishings combined with modern ... Property Details
Close to the Beach
Priced at July ('19 - 19) $14,000; August(LD) ('19 - 19) $16,000; July/August(LD) ('19 - 19) $28,000 Beds: 4 Baths: 2 Sq. Feet: 1548Four bedroom, two bath one level home with pool on Shelter Island. Perfect summer retreat in a great ... Property Details
Shelter Island Modern Close to Beach
Priced at July ('19 - '19) $24,000; August(LD) ('19 - '19, $26k Aug no LD) $30,000 Beds: 4 Baths: 4 Sq. Feet: 3280Within close proximity to a wide sandy bay beach, this pristine four bedroom, four bath cedar clad ... Property Details
Sleek Dering Harbor Village with Pool
Priced at August(LD) $33,000 Beds: 5 Baths: 4 Sq. Feet: 2753Located on a quiet lane in the heart of Dering Harbor Village, this classic Victorian has been ... Property Details
Historic Shelter Island
Priced at MD-LD ('19 - 19) $24,000 Beds: 4 Baths: 2.5 Sq. Feet: 2445The former Shelter Island library has been renovated to include four bedrooms, two and a half baths ... Property Details
Lush and Lovely Shelter Island with Pool
Priced at July/August(LD) ('19 - '19) $35,000 RENTED Beds: 4 Baths: 4 Sq. Feet: 2424Located a half block from sandy beach, this deer free property has beautiful gardens and pool with ... Property Details
Shelter Island Languor on Lily Pond
Priced at July ('19 - 19) $7,500 RENTED; August(LD) ('19 - 19) $8,500 RENTED Beds: 3 Baths: 2.5 Sq. Feet: 2750This sunny three story shingle-style house sits on approximately 1.1 +/- acres fronting Lily Pond. A ... Property Details
Shelter Island Sunset Cottage
Priced at August(LD) ('19 - 19) $13,750; July/August(LD) ('19 - 19) $24,500 RENTED Beds: 4 Baths: 1.5 Sq. Feet: 1456This delightful water view cottage is a stone's throw from Sunset Beach, Perlman Music Program, Camp ... Property Details
Historic Sanctuary
Priced at MD-LD ('19 - 19) $35,000 RENTED Beds: 5 Baths: 3 Sq. Feet: 4872This 1848 colonial revival boasts five bedrooms, three baths and a partial basement on 1 +/- acre. ... Property Details
Shelter Island Traditional with Deep Water Dock
Priced at July ('19 - 19) $22,500 RENTED; August(LD) ('19 - 19 (Aug only, $22,500)) $25,000 RENTED Beds: 3 Baths: 3 Sq. Feet: 2200This sun filled traditional is located at waters edge, within close proximity to sandy beach. This ... Property Details
Pristine Renovated Farmhouse Close to Boating
Priced at Weekly (08/19/19 - 09/02/19) $5,500 Beds: 3 Baths: 2.5 Sq. Feet: 2151Sitting pretty on the southwest side of Shelter Island within close proximity to beach and boating, ... Property Details
Spectacular Dering Harbor Waterfront Modern
Priced at S Term (08/01/19 - 08/15/19) $30,000 Unavailable Beds: 4 Baths: 3.5 Sq. Feet: 4634Dering Harbor Vacation Rental New to the rental market! One step into this glass-walled modern with ... Property Details
Shelter Island Water View Cottage
Priced at August(LD) ('19 - 19) $12,000 RENTED Beds: 2 Baths: 2 Sq. Feet: 1355Shelter Island Heights Vacation Rental This cottage, located in desirable Shelter Island Heights, ... Property Details
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