Rental Listings
Intimate Island Getaway with Stunning 180-degree Waterfront Views
Priced at Custom (05/23/25 - 09/01/25) $40,750; July/August (07/01/25 - 09/01/25) $32,750 Beds: 4 Baths: 1.5 Sq. Feet: 1456Rental Registration #2024-L-0012. This delightful water view cottage is a stone's throw from Sunset ... Property Details
Shelter Island Traditional with Deep Water Dock
Priced at MD-LD ('25 - 25) $95,000; July/August(LD) ('25 - 25) $75,000; July ('25 - 25) $35,000; August(LD) ('25 - 25) $40,000 Beds: 3 Baths: 3 Sq. Feet: 2200Shelter Island, NY Vacation Rental Rental Registration #2023-L-0167. This sun filled traditional is ... Property Details
Shelter Island Cottage Close Proximity to Sandy Beach
Priced at November ('24 - 24) $2,200; December ('24 - 24) $2,200; January ('25 - 25) $2,200; February ('25 - 25) $2,200; March ('25 - 25) $2,200; April ('25 - 25) $2,200 Beds: 3 Baths: 1.5 Sq. Feet: 1935Rental Registration #0159. New to the rental market! This well maintained, sunny cottage is located ... Property Details
Quaint and Convenient Shelter Island
Priced at June ('25 - 25) $7,700; August(LD) ('25 - 25) $9,900; September ('25 - 25) $7,700; October ('25 - 25) $5,500 Beds: 2 Baths: 2 Sq. Feet: 892Rental Registration #2023-L-0007. A delightful two-bedroom, two-bath cottage in Shelter Island's ... Property Details
Summer Beach Cottage on Shelter Island
Priced at MD-LD ('24 - 24) $28,000 RENTED; Year Round (09/01/24 - 09/30/25) $40,000 RENTED Beds: 2 Baths: 1 Sq. Feet: 700Shelter Island Summer Beach Cottage for Rent Rental Registration #2023-L-0105. Located within close ... Property Details
Fabulous Shelter Island Sandy Beach House with Pool
Priced at Two Weeks (07/14/25 - 08/28/25) $12,110 Beds: 5 Baths: 5 Sq. Feet: 2954Rental Registratino #2022-L-0114. Located in the estate section, this sprawling five bedroom ranch ... Property Details
Shelter Island Quiet Contemporary with Pool
Priced at July/August(LD) ('25 - 25) $59,000, July ('25 - 25) $27,000; August(LD) ('25 - 25, w/o LD $31k) $32,000 Beds: 3 Baths: 2 Sq. Feet: 2500Rental Registration #2023-L-0127. Located in the Conservancy Estates area on the south side of ... Property Details
Shelter Island Ram Island Beachfront with Pool
Priced at June ('25 - 25) $26,500; September ('25 - 25) $26,500 Beds: 4 Baths: 2 Sq. Feet: 1500Rental Registration #2023-L-0001. Set on 1.8 +/- waterfront acres on Ram Island by Coecles Harbor ... Property Details
Clean East Hampton Contemporary with Pool and Tennis
Priced at July ('25 - 25) $27,000; August(LD) ('25 - 25) $29,000 Beds: 4 Baths: 2 Sq. Feet: 1850Rental Registration #23-1112. No groups or shares. Located approximately 1.5 +/- miles from town on ... Property Details
Shelter Island Creekfront with Dock and Pool
Priced at June ('25 - 25) $18,000; July ('25 - 25) $25,500 RENTED; August(LD) ('25 - 25) $30,600 RENTED Beds: 4 Baths: 3 Sq. Feet: 3000Rental Registration #2023-L-0029. This four-bedroom, three-bath creekfront Traditional occupies .75 ... Property Details
Sunny Bayfront on Shelter Island
Priced at Custom (09/01/25 - 09/30/25) $8,000 Beds: 4 Baths: 2.5 Sq. Feet: 1504Rental Registration #2023-L-0041. This contemporary offers four bedrooms and two and one half baths ... Property Details
Traditional Pond Front Shelter Island
Priced at MD-LD ('25 - 25) $50,000; June ('25 - 25) $15,000; July ('25 - 25) $20,000; August(LD) ('25 - 25) $25,000 Beds: 4 Baths: 2.5 Sq. Feet: 3000Rental Registration #2024-L-0024. This Victorian Traditional has four bedrooms, two and one half ... Property Details
