Rental Listings
Lush and Lovely Shelter Island with Pool
Priced at June ('19 - 19) $12,000; 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 MD-LD ('19 - 19) $33,500; June (05/24/19 - 06/30/19) $10,000; July ('19 - 19) $11,750; August(LD) ('19 - 19) $13,750; July/August(LD) ('19 - 19) $24,500 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 S Term ('19 - '19, 2 wks) $10,000 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 June ('19 - 19) $5,000; August(LD) ('19 - 19) $12,000; Winter (09/03/18 - 06/30/19 $2,750/month) $16,500; S Term (06/01/19 - 06/14/19) $2,500 Beds: 2 Baths: 2 Sq. Feet: 1355Shelter Island Heights Vacation Rental This cottage, located in desirable Shelter Island Heights, ... Property Details
Shelter Island Cottage with Pool, Boat Slip & Association Beach
Priced at MD-LD ('19 - '19) $30,000 RENTED; July ('19 - '19) $10,000 RENTED; August(LD) ('19 - '19) $13,000 RENTED; Y/R ('19 - '19) $30,000 RENTED; S Term (08/01/19 - 09/03/19) $4,000 RENTED Beds: 3 Baths: 2 Sq. Feet: 1600South Ferry & Wades Beach Vacation Rental This clean and straightforward Shelter Island cottage ... Property Details
Shelter Island Cottage Close Proximity to Sandy Beach
Priced at MD-LD (06/01/19 - 09/02/19) $17,000 RENTED; June ('19 - '19) $5,000 RENTED; July ('19 - '19) $6,500 RENTED; August(LD) ('19 - '19) $7,000 RENTED Beds: 3 Baths: 1.5 Sq. Feet: 1935New to the rental market! This well maintained, sunny cottage is located only a few doors from a ... Property Details
Shelter Island Bay Front Traditional with Pool
Priced at MD-LD ('19 - 19) $88,000; June ('19 - 19) $15,000; July ('19 - 19) $30,000; August(LD) ('19 - 19) $40,000; July/August(LD) ('19 - 19) $80,000 Beds: 4 Baths: 5 Sq. Feet: 2774Enjoy spectacular views of West Neck Bay and Creek at this renovated four-bedroom, five-bath home on ... Property Details
Hilltop Traditional with Pool Close Proximity to Beach
Priced at July ('19 - '19) $20,000; August(LD) ('19 - '19) $22,000 Beds: 3 Baths: 2 Sq. Feet: 2962Located within close proximity to Sunset Beach, ferry and golf, this hilltop Traditional is in a ... Property Details
Shelter Island Victorian with Water View and Pool
Priced at August(LD) ('19 - 19**$6,500 per wk**) $28,000; S Term (08/01/19 - 09/02/19 per week) $6,500 Beds: 5 Baths: 4 Sq. Feet: 4675This Victorian-style home on a shy acre is in the Hay Beach area with pretty water views, a pillared ... Property Details
Charming Cottage Close Proximity to Beach
Priced at S Term (08/23/19 - 09/02/19) $7,000; Extended Season (09/02/19 - 09/19/19) $3,000 Beds: 3 Baths: 2 Sq. Feet: 1472If you enjoy a quiet cottage on a country lane within close proximity to sugar sandy beaches, look ... Property Details
Freshly Renovated Shelter Island Cottage on Golf Course
Priced at August(LD) (08/01/19 - 09/02/19) $12,500 RENTED; Y/R (09/03/19 - 09/03/20) $3,000 Beds: 2 Baths: 2 Sq. Feet: 1888This delightful cottage has just completed a beautiful renovation and is sure to please. There are ... Property Details
Shelter Island Pristine Waterfront Compound with Pool and Dock
Priced at MD-LD ('19 - '19) $325,000; June ('19 - '19, two weeks $37,500) $75,000; July ('19 - '19, two weeks $65,000) $125,000; August(LD) ('19 - '19, two weeks: $85,000 w/o LD $82,500) $150,000 Beds: 5 Baths: 5 Sq. Feet: 3000In one of the most pristine natural settings on Shelter Island, Congdon's Point is a hidden ... Property Details
Quaint and Convenient Shelter Island
Priced at Ext. Season (09/03/19 - 09/30/19) $6,500; Winter (10/01/19 - 10/31/19) $5,000 Beds: 2 Baths: 2 Sq. Feet: 892A delightful two-bedroom, two-bath cottage in Shelter Island's Montclair Colony. Features include a ... Property Details
Iconic 1884 Shelter Island Heights Seacoast Estate
Priced at June ('19 - '19) $25,000 Beds: 7 Baths: 8 Sq. Feet: 7165This 1884 Queen Anne style waterfront estate possesses an extraordinary provenance, and has been ... Property Details
Shelter Island Heights Contemporary
Priced at MD-LD ('19 - '19) $35,000; July ('19 - '19) $13,000; August(LD) ('19 - '19) $15,000 Beds: 3 Baths: 2 Sq. Feet: 1584Located a stone's throw from Shelter Island Country Club, Crescent Beach, North Ferry and Shelter ... Property Details
Distinctive Shelter Island Heights Gem
Priced at Weekly (05/24/19 - 06/15/19) $2,000; S Term (05/24/19 - 06/15/19) $4,500; S Term (08/18/19 - 09/14/19) $6,000 Beds: 4 Baths: 2 Sq. Feet: 2154This beautifully renovated 1890 Shelter Island traditional offers tasteful appointments and ... Property Details
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