Rental Listings
Shelter Island Waterfront with Pool
Priced at Two Weeks (08/01/26 - 09/07/26) $15,000 Beds: 4 Baths: 3 Sq. Feet: 2200Rental Registration #2026-L-0079. Spacious four bedroom, three bath contemporary with beautiful ... Property Details
Shelter Island Waterview Cottage
Priced at September ('26 - 26) $20,000 Beds: 4 Baths: 3.5 Sq. Feet: 2675Rental Registration #2026-L-0028. Set on a peaceful 0.75-acre property in the heart of Shelter ... Property Details
Shelter Island Newly Renovated Water View Cottage with Pool
Priced at July/August(LD) ('26 - 26) $85,000; Custom (07/15/26 - 09/07/26) $70,000; August(LD) ('26 - 26) $50,000; September ('26 - 26) $25,000; October ('26 - 26) $15,000; November ('26 - 26) $7,500; December ('26 - 26) $7,500; January ('27 - 27) $5,600; February ('27 - 27) $5,600; March ('27 - 27) $5,600 Beds: 3 Baths: 3.5 Sq. Feet: 1836Rental Registration #2026-L-0004. Located on a private Ram Island lane, this stylish and uplifting ... Property Details
Charming Cottage
Priced at Custom (08/10/26 - 09/08/26) $18,000 Beds: 2 Baths: 1 Sq. Feet: 1000Rental Registration #2025-L-0053. Located within close proximity to popular beaches, this two ... Property Details
Gracious Shelter Island with Pool
Priced at July ('26 - 26) $25,000 RENTED; August(LD) ('26 - 26) $40,000 RENTED; Year Round (09/07/26 - 08/31/27) $78,000; September (09/07/26 - 09/30/26) $5,000; October ('26 - 26) $5,000; November ('26 - 26) $5,000; December ('26 - 26) $5,000; January ('27 - 27) $5,000; February ('27 - 27) $5,000; March ('27 - 27) $5,000; April ('27 - 27) $5,000; May ('27 - 27) $5,000; June ('27 - 27) $5,000 Beds: 5 Baths: 2Rental Registration #2025-L-0135. This classic Shelter Island country home was recently renovated by ... Property Details
Chic Shelter Island Barn with Pool and Day Dock
Priced at July ('26 - 26) $35,000 RENTED; Custom (08/28/26 - 09/07/26) $8,000; Custom (09/08/26 - 09/30/26) $8,000; October ('26 - 26) $8,000; November ('26 - 26) $8,000; December ('26 - 26) $8,000; January ('27 - 27) $8,000; February ('27 - 27) $8,000; March ('27 - 27) $8,000; April ('27 - 27) $8,000; May ('27 - 27) $8,000; June ('27 - 27) $8,000 Beds: 2 Baths: 2 Sq. Feet: 1560Rental Registration #2025-L-0006. This chic barn-style house is located off a quiet lane and is ... Property Details
Bayview Contemporary Shelter Island
Priced at August(LD) ('26 - 26) $26,000; September ('26 - 26) $14,000; Two Weeks (09/01/26 - 09/30/26) $7,500 Beds: 4 Baths: 3 Sq. Feet: 2600Rental Registration #2025-V-002. This sunny Contemporary with slices of water views has loads of ... Property Details
Shelter Island Spacious Traditional with Pool Close to Beach
Priced at Weekly (08/23/26 - 09/05/26) $10,800 Beds: 5 Baths: 3.5 Sq. Feet: 2552Rental Registration #2026-L-0080. Enjoy your summer at this spacious traditional with plenty of room ... Property Details
Newly renovated 1911 Historic Estate with Pool on 6 Acres
Priced at Two Weeks (08/24/26 - 09/07/26) $30,000 Beds: 6 Baths: 4.5 Sq. Feet: 2790Rental Registration #2025-L-0031. This newly renovated 1911 home combines old world charm with ... Property Details
Shelter Island Waterfront with Pool and Dock
Priced at MD-LD ('26 - 26) $100,000; August(LD) ('26 - 26) $50,000; September ('26 - 26) $20,000 Beds: 4 Baths: 2 Sq. Feet: 2200Rental Registration #2026-L-0003. Charming waterfront cottage offers views of the harbor from nearly ... Property Details
Farmhouse with Pool
Priced at Weekly (08/16/26 - 09/07/26) $4,200; Custom (08/16/26 - 09/07/26) $9,500 Beds: 4 Baths: 2.5 Sq. Feet: 2522Rental Registration #2025-L-0107. New to the Market. Hidden behind tall privet hedges with wide ... Property Details
Shelter Island Getaway with Stunning 180-degree Waterfront Views
Priced at July/August(LD) ('26 - 26) $24,500; August(LD) ('26 - 26) $13,500 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
Quaint and Convenient Shelter Island
Priced at August(LD) ('26 - 26) $9,900; 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 RENTED; September (09/08/26 - 09/30/26) $15,000 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/July (06/27/26 - 07/29/26) $23,000 RENTED; 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
Turn Of The Century Shelter Island Waterfront
Priced at August(LD) ('26 - 26, w/o LD $35k) $40,000; September ('26 - 26) $20,000 Beds: 4 Baths: 2 Sq. Feet: 2500Rental Regisstration #2026-L-0045. Located on the harbor, this classic turn of the century Farmhouse ... Property Details
Shelter Island Ram Island Beachfront with Pool
Priced at 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 RENTED; 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
