Rental Listings
Shelter Island Elegant Bayfront with Deepwater Dock
Priced at September ('24 - 24) $12,000; October ('24 - 24) $7,500; November ('24 - 24) $7,000; July ('25 - 25) $55,000; Two Weeks (07/01/25 - 07/31/25) $27,500; August(LD) ('25 - 25) $60,000; Two Weeks (08/01/25 - 08/31/25) $30,000 Beds: 5 Baths: 4.5 Sq. Feet: 4467Rental Registration #2024-L-0046. First offering! This elegant traditional graces a slight bluff ... Property Details
Shelter Island Newly Renovated Water View Cottage with Pool
Priced at August(LD) (24 - 24) $55,000 RENTED; September ('24 - 24) $25,000; October ('24 - 24) $15,000; November (24 - 24) $7,500; December ('24 - 24) $7,500; January ('25 - 25) $7,500; February ('25 - 25) $7,500; March ('25 - 25) $7,500 Beds: 3 Baths: 3.5 Sq. Feet: 1836Rental Registration #2024-L-0028. Located on a private Ram Island lane, this stylish and uplifting ... Property Details
Shelter Island Modern near Marina
Priced at September ('24 - 24) $8,000; October ('24 -24) $6,000 Beds: 1 Baths: 1 Sq. Feet: 1332Rental Registration #2023-L-0125. This sleek, modernist home, built in 2017 is an idyllic spot to ... Property Details
Shelter Island Beach Cottage
Priced at September ('24 - 24) $9,000 Beds: 3 Baths: 2 Sq. Feet: 1428Rental Registration #2022-L-0016. Shelter island's south side offers expansive Shell Beach and ... Property Details
Shelter Island Charming Cape Cod
Priced at September ('24 - 24) $10,000; October ('24 - 24) $7,000 Beds: 3 Baths: 2 Sq. Feet: 1660Rental Registration #2023-L-0072. Located within close proximity to ferry, shops and beach, this ... Property Details
1887 Dering Harbor Village Victorian with Pool and Dock
Priced at May (05/01/25 - 05/28/25) $20,000; June (05/30/25 - 06/30/25) $25,000; July ('25 - 25) $45,000; August(LD) ('25 - 25) $50,000; Custom (09/03/25 - 09/30/25) $30,000 Beds: 5 Baths: 3.5 Sq. Feet: 4053This charming, renovated 1887 Victorian is located on a quiet lane on 1.44+/- acres in the Village ... Property Details
Shelter Island Traditional with Pool bordering Preserve
Priced at Weekly (09/01/24 - 09/30/24) $12,000; Weekly (10/01/24 - 10/31/24) $7,500; Weekly (11/01/24 - 11/30/24) $5,500; Weekly (12/01/24 - 12/31/24) $6,000 Beds: 5 Baths: 5.5 Sq. Feet: 4700Rental Registration #2023-L-0043. This grand compound bordering parkland is spectacular. The main ... Property Details
Shelter Island Quiet Ranch with Pool
Priced at Custom (09/04/24 - 09/15/24) $5,500 Beds: 3 Baths: 2 Sq. Feet: 1247Rental Registration #2023-V-0018. Located just outside the Heights within close proximity to ferry ... Property Details
Shelter Island Quintessential Beach House
Priced at July ('24 - 24) $31,000 RENTED; August(LD) ('24 - 24) $35,100 RENTED; Custom (09/01/24 - 09/24/24) $18,000 RENTED Beds: 4 Baths: 2 Sq. Feet: 2406Rental Registration #2022-L-0040. This distinctive beach house is what summer on Shelter Island is ... Property Details
Sun-Filled Shelter Island Charming Cottage Close to Beach
Priced at September (09/03/24 - 09/23/24) $12,000 Beds: 4 Baths: 3 Sq. Feet: 2400Rental Registration #2024-L-0026. This sun filled one level cottage is located within a stone's ... Property Details
Shelter Island Renovated Cottage near Beach
Priced at Two Weeks (09/01/24 - 09/30/24) $6,000; September ('24 - 24) $12,000; October ('24 - 24) $9,000; Two Weeks (10/01/24 - 10/31/24) $5,000 Beds: 3 Baths: 2 Sq. Feet: 1636Rental Registration #2023-L-0141. This clean and sweet cottage has recently been renovated and is ... Property Details
5 Bedroom Colonial with Infinity Pool and Waterfront Beach
Priced at Custom (09/06/24 - 09/30/24) $30,000 RENTED; October ('24 - 24) $18,000; November ('24 - 24) $15,000; December ('24 - 24) $15,000 Beds: 5 Baths: 6.5 Sq. Feet: 5670Rental Registration #2023-V-0002. This charming 5 bedroom, 6 bath colonial has an open floor plan ... Property Details
Shelter Island Spacious Traditional with Pool Close to Beach
Priced at October ('24 - 24) $31,000 Beds: 5 Baths: 3.5 Sq. Feet: 2552Rental Registration #2023-V-0039 & 2023-L-0133. Enjoy your summer at this spacious traditional with ... Property Details
Cheery Renovated Shelter Island Farmhouse near Marina
Priced at Year Round (09/09/24 - 09/08/25) $62,000 Beds: 4 Baths: 2.5 Sq. Feet: 2052Rental Registration #2023-L-0172 This sun filled farmhouse has been recently renovated and boasts an ... Property Details
Shelter Island Close Proximity to Town and Beach
Priced at July ('24 - 24) $13,000 RENTED; August ('24 - 24) $14,000 RENTED; September (09/03/24 - 09/30/24) $9,500 RENTED Beds: 3 Baths: 1 Sq. Feet: 1600Rental Registration# 19L-2133. This fresh and updated upside down modern on .75 acre is located ... Property Details
Enchanting Shelter Island Heights Union Chapel
Priced at September ('24 - 24) $8,000; October ('24 - 24) $6,000 Beds: 3 Baths: 1.5 Sq. Feet: 1194Rental Registration #2023-L-0112. The homes around Union Chapel in the Heights are always in demand ... Property Details
Shelter Island Waterfront with Pool and Dock
Priced at August(LD) ('24 - 24) $60,000 RENTED; September ('24 - 24) $25,000 RENTED; October ('24 - 24) $15,000 Beds: 4 Baths: 2 Sq. Feet: 2200Rental Registration #2024-L-0022. Charming waterfront cottage offers views of the harbor from nearly ... Property Details
Farmhouse with Pool
Priced at Weekly (09/03/24 - 09/30/24) $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
Pristine Shelter Island Bay View with Dock Access
Priced at September ('24 - 24) $20,000 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 Cottage Close Proximity to Sandy Beach
Priced at October ('24 -24) $2,500; November ('24 - 24) $2,500; December ('24 - 24) $2,500; January ('25 - 25) $2,500; February ('25 - 25) $2,500; March ('25 - 25) $2,500; April ('25 - 25) $2,500 Beds: 3 Baths: 1.5 Sq. Feet: 1935Rental Registration #0159. New to the rental market! This well maintained, sunny cottage is located ... Property Details
