Rental Listings
Fabulous Shelter Island Watefront Cottage
Priced at August(LD) ('19 - '19) $12,000 Beds: 3 Baths: 2 Sq. Feet: 1267Simple and sweet, located on inlet of a harbor, this three bedroom, two bath cottage has sunsets and ... Property Details
Shelter Island Pond Front Traditional
Priced at June ('19 - '19 ($6,000 per week)) $24,000; July ('19 - '19 ($7,000 per week)) $32,000; August(LD) ('19 - '19 ($7,000 per week)) $32,000; S Term (06/01/19 - 06/30/19**2 week min) $6,000 Beds: 4 Baths: 3.5 Sq. Feet: 2600This lovely four bedroom, three and one-half bath home perched atop a hill overlooks Fresh Pond. ... Property Details
Silver Beach Mid Century Seclusion
Priced at S Term (08/19/19 - 09/02/19**$7K per week**) $14,000 Beds: 3 Baths: 2 Sq. Feet: 2000This original mid century modern has water views and is a lovely spot to spend the summer. There are ... Property Details
Shelter Island Waterfront with Pool, Dock and Tennis
Priced at August(LD) ('19 - 19) $45,000 Beds: 4 Baths: 3.5 Sq. Feet: 3246Located within close proximity to the South Ferry and surrounded by nature, this waterfront home ... Property Details
Shelter Island Farmhouse with Pool and Pool Cabana
Priced at August(LD) (08/01/19 - 09/02/19) $20,000; S Term (08/18/19 - 09/02/19) $12,000 Beds: 3 Baths: 2.5 Sq. Feet: 1750Located just outside the Heights, this quaint 1898 farmhouse has incredible charm and character. The ... Property Details
Shelter Island Spacious Waterfront with Pool and Dock
Priced at July ('19 - '19) $55,000; August(LD) ('19 - '19) $60,000; July/August(LD) ('19 - '19) $110,000 Beds: 5 Baths: 5 Baths, 2 Half Sq. Feet: 4941A memorable vacation can be in your future at this spacious waterfront home with close to 5,000 sf ... Property Details
Shelter Island Modern and Clean Close to Beach
Priced at MD-LD ('19 - '19) $38,000; June ('19 - '19) $10,000; July ('19 - '19) $14,000; August(LD) ('19 - '19) $16,000; Winter (11/01/18 - 5/01/19 (monthly)) $2,800 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 - 09/15/19) $125,000 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 Bayfront with Pool
Priced at MD-LD ('19 - '19) $125,000; June ('19 - '19) $35,000; July ('19 - '19) $45,000; August(LD) ('19 - '19) $50,000 Beds: 5 Baths: 3 Sq. Feet: 4297This spacious contemporary on Gardiners Bay offers views to "Bug Light" lighthouse and has room for ... 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; S Term ('19 - 19) $10,000 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 Winter (01/11/19 - 05/31/19) $42,000; S Term (08/01/19 - 08/31/19 wkly) $2,765 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(LD) ('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; July ('19 - 19) $4,500; August(LD) ('19 - 19) $6,000 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 Apr, May, Sep, Oct) $8,000; S Term ('19 - '19 Memorial Weekend) $4,000 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; July ('19 - '19) $14,000; August(LD) ('19 - '19) $16,000; Winter (09/03/18 - 04/30/19) $2,995 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 Shelter Island with Pool
Priced at MD-LD ('19 - 19) $35,000; June ('19 - 19) $14,000; 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 June ('19 - '19) $16,000; July ('19 - '19) $24,000; August(LD) ('19 - '19 26k Aug no LD) $30,000; Winter ('18 - '19) $25,000 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 June (05/22/19 - 06/30/19) $22,000; August(LD) (08/01/19 - 09/02/19) $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 (07/15/19 - 07/31/19) $15,000; August(LD) ('19 - 19) $25,000; July/August(LD) (07/15/19 - 09/02/19) $35,000; S Term ('19 - 19) $12,000 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
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