Rental Listings
Shelter Island Modern Close to Beach
Priced at June ('26 - 26) $30,000; Two Weeks (07/15/26 - 07/31/26) $20,000 Beds: 4 Baths: 4 Sq. Feet: 2120Rental Registration #2026-L-0002. Within close proximity to a wide sandy bay beach, this pristine ... Property Details
Lush and Lovely Shelter Island with Pool
Priced at Custom (07/17/26 - 07/31/26) $21,000; August ('26 - 26) $42,000 Beds: 4 Baths: 4 Sq. Feet: 2424Rental Registration #2026-L-0030. Located a half block from sandy beach, this deer free property has ... Property Details
Shelter Island Getaway with Stunning 180-degree Waterfront Views
Priced at Custom (05/23/26 - 09/07/26) $39,500; July/August (07/01/26 - 09/07/26) $29,500; July ('26 - 26) $17,500; August(LD) ('26 - 26) $19,500 Beds: 4 Baths: 1.5 Sq. Feet: 1456Rental Registration #2026-L-0013. A romantic and secluded summer getaway. Enjoy a front row seat to ... Property Details
Shelter Island Traditional with Deep Water Dock
Priced at Custom (05/22/26 - 07/31/26) $65,000; MD-LD ('26 - 26) $90,000; July ('26 - 26) $35,000; July/August(LD) ('26 - 26) $70,000; August(LD) ('26 - 26, w/o LD $35k) $43,000 Beds: 3 Baths: 3 Sq. Feet: 2200Shelter Island, NY Vacation Rental Rental Registration #2025-L-0137. This sun filled traditional is ... Property Details
Shelter Island Cottage Close Proximity to Sandy Beach
Priced at June ('26 - 26) $7,000; June/July ('26 - 26) $15,000; Two Weeks (06/01/26 - 07/31/26) $5,000; July ('26 - 26) $10,000 Beds: 3 Baths: 1.5 Sq. Feet: 1935Rental Registration #2025-L-0118. New to the rental market! This well maintained, sunny cottage is ... Property Details
Quaint and Convenient Shelter Island
Priced at June ('26 - 26) $7,700; August(LD) ('26 - 26) $9,900; Custom (08/01/26 - 08/15/26) $4,950; September (09/08/26 - 09/30/26) $7,700; October ('26 - 26) $5,500 Beds: 2 Baths: 2 Sq. Feet: 892Rental Registration #2024-L-0106. A delightful two-bedroom, two-bath cottage in Shelter Island's ... Property Details
Shelter Island Spacious Traditional near Beach
Priced at July ('26 - 26) $39,000 RENTED; August(LD) ('26 - 26) $39,000 Beds: 4 Baths: 2.5 Sq. Feet: 2682Spacious Shelter Island Rental Rental Registration #2024-L-0111. Located a stone's throw from wide ... Property Details
Shelter Island Water View with Pool
Priced at June ('26 - 26) $14,000; July ('26 - 26) $23,000; August(LD) ('26 - 26) $23,000 RENTED; September ('26 - 26) $14,000 Beds: 4 Baths: 2 Sq. Feet: 1932Rental Registration #2025-L-0048. Located a stone's throw from sandy beach just across the street, ... Property Details
Shelter Island Pristine Traditional with Pool
Priced at July ('26 - 26) $35,000; Two Weeks (07/01/26 - 07/31/26) $20,000; Two Weeks (08/01/26 - 08/18/26) $20,000; Custom (08/01/26 - 08/18/26) $22,000 Beds: 4 Baths: 3 Sq. Feet: 3194Rental Registration #2026-L-0022. This recently built traditional is located on one acre within ... Property Details
Shelter Island Ram Island Beachfront with Pool
Priced at June ('26 -26) $26,500; September ('26 - 26) $26,500 Beds: 4 Baths: 2 Sq. Feet: 1500Rental Registration #2026-L-0024. 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 ('26 - 26) $27,000; August(LD) ('26 - 26, w/o LD $29k) $32,000; September (09/11/26 - 09/30/26) $20,000 Beds: 4 Baths: 2 Sq. Feet: 1850Rental Registration #25-972. No groups or shares. Located approximately 1.5 +/- miles from town on ... Property Details
Stunning Shelter Island Little Ram Waterfront with Pool
Priced at July ('26 - 26) $30,000 RENTED, August(LD) ('26 - 26) $35,000 RENTED Beds: 4 Baths: 3 Sq. Feet: 1584Rental Registration #2026-L-0001. Located on Little Ram Island on Gardiners Bay, this four bedroom, ... Property Details
Shelter Island Languor with Pool and Guest House
Priced at MD-LD ('26 - 26) $78,000; Custom (05/22/26 - 06/30/26) $22,000; June ('26 - 26) $17,000; July ('26 - 26) $24,500; August(LD) ('26 - 26, w/o LD $27K) $32,000 Beds: 5 Baths: 4 Sq. Feet: 2300Rental Registration #2025-L-0010. This five bedroom, four bath traditional has an open living room, ... Property Details
Shelter Island Close Proximity to Beach with Pool
Priced at Year Round (1/1/26 - 12/31/26) $60,000; MD-LD ('26 -26) $50,000; June ('26 - 26) $8,000; July/August(LD) ('26 - 26) $35,000; July ('26 - 26) $15,000; August(LD) ('26 - 26, w/o LD $20K) $25,000 Beds: 3 Baths: 2 Sq. Feet: 1600Rental Registration #2025-L-0031. A sweet ranch house on 1.5 +/- acres within close proximity to ... Property Details
Shelter Island Retreat with Tennis and Pool
Priced at June ('26 - 26) $24,000 RENTED; July ('26 - 26) $32,000; August ('26 - 26) $40,000 Beds: 5 Baths: 3 Sq. Feet: 2697Rental Registration #2025-L-0036. Enjoy this spacious five bedroom, three bath raised contemporary ... Property Details
Victorian Shelter Island Heights
Priced at June ('26 - 26) $19,000; August(LD) ('26 - 26) $23,750 RENTED Beds: 3 Baths: 2 Sq. Feet: 1500Rental Registraton #2026-L-006. This lovely iconic 1800's Heights Victorian sits on a corner with ... Property Details
