Rental Listings
Shelter Island Adorable Bungalow near Marina
Priced at June ('25 - 25) $8,000; July ('25 - 25) $8,500; August(LD) ('25 - 25) $9,500 Beds: 3 Baths: 2 Sq. Feet: 1200Rental Registration #2023-L-0083. Located in Montclair Colony is this charming cottage with three ... Property Details
Shelter Island Expanded Cottage with Pool
Priced at June ('25 - 25) $18,000; Two Weeks (06/01/25 - 06/30/25) $10,000; Two Weeks (07/01/25 - 09/01/25) $14,000; July ('25 - 25) $26,000; August(LD) ('25 - 25) $26,000 Beds: 3 Baths: 3 Sq. Feet: 1933Rental Registration #2023-V-0003. Located within close proximity of association beaches, this ... Property Details
Farmhouse with Pool
Priced at Custom (05/01/25 - 05/25/25) $4,000; Short-Term (05/30/25 - 06/16/25) $10,500; Weekly (08/16/25 - 09/01/25) $4,200; Two Weeks (08/16/25 - 09/01/25) $7,500; Weekly (09/02/25 - 09/30/25) $3,200; September (09/02/25 - 09/30/25) $10,000; October (10/01/25 - 10/31/25) $6,000; Winter (11/01/25 - 04/30/26) $3,500 Beds: 4 Baths: 2.5 Sq. Feet: 2522Rental Registration #2023-L-0111. New to the Market. Hidden behind tall privet hedges with wide ... Property Details
Charming 1920’s Waterfront Cottage with Dock
Priced at Custom (05/23/25 - 06/30/25) $8,500; July ('25 - 25) $11,750; August(LD) ('25 - 25) $11,750 Beds: 1 Baths: 2 Sq. Feet: 875Rental Registration #23-V-0016. Located within short distance to the ferry, Heights and beach, this ... Property Details
Pristine Shelter Island Bay View with Dock Access
Priced at July ('25 - 25) $22,000; August ('25 - 25) $25,000; September ('25 - 25) $18,000 Beds: 3 Baths: 2 Sq. Feet: 1608Rental Registration #2023-L-0132. This recently renovated ranch has a sunny living room, kitchen ... Property Details
Shelter Island Modern Close to Beach
Priced at June (05/30/25 - 06/30/25) $26,000; July ('25 - 25) $36,000; August(LD) ('25 - 25, w/o LD $36k) $39,000 RENTED Beds: 4 Baths: 4 Sq. Feet: 2120Rental Registration #2024-L-0019. Within close proximity to a wide sandy bay beach, this pristine ... Property Details
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 June/July ('25 - 25) $17,000; June ('25 - 25) $8,000; July ('25 - 25) $12,000 Beds: 3 Baths: 1.5 Sq. Feet: 1935Rental Registration #2023-L-0159. New to the rental market! This well maintained, sunny cottage is ... 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 #2024-L-0106. 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) $42,000, July ('25 - 25) $20,000; August(LD) ('25 - 25) $22,000 Beds: 3 Baths: 2 Sq. Feet: 2500Rental Registration #2025-L-0008. Located in the Conservancy Estates area on the south side of ... Property Details
Fabulous Shelter Island Modern with Pool
Priced at Two Weeks (06/01/25 - 06/30/25) $8,500; Two Weeks (07/01/25 - 07/31/25) $14,500; Two Weeks (08/01/25 - 09/01/25) $14,500; Two Weeks (09/02/25 - 09/30/25) $8,000 Beds: 3 Baths: 3 Sq. Feet: 1338Rental Registration #2024-L-0093. Located within close proximity to marina, this sleek modernist, ... Property Details
Quiet Shelter Island Beach Area Farmhouse With Pool
Priced at August(LD) ('25 - 25) $26,000 Beds: 5 Baths: 3 Sq. Feet: 3126Rental Registration #2023-V-0009. This turn of the century farmhouse on 1.25 +/- acres was one of ... Property Details
Turn Of The Century Shelter Island Waterfront
Priced at June ('25 - 25) $17,000; July/August(LD) ('25 - 25) $52,500 RENTED; Custom (09/06/25 - 09/30/25) $20,000 Beds: 4 Baths: 2 Sq. Feet: 2500Rental Regisstration #2023-L-0177. Located on the harbor, this classic turn of the century Farmhouse ... 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 Shelter Island Waterfront with Dock and Sandy Beach
Priced at August ('25 - 25) $49,500; September ('25 - 25) $25,000 Beds: 4 Baths: 3 Sq. Feet: 2799Rental Registration #2023-V-0037. Set close to wide sandy beach on slight bluff, this sunny ... Property Details