Rental Listings
Shelter Island Cottage Close to Beach
Priced at April ('25 - 25) $3,500 Beds: 2 Baths: 1 Sq. Feet: 1248Rental Registration #2023-L-0165. This sun-filled cedar shingled cottage on a quiet lane, and within ... Property Details
Shelter Island Retreat with Pool Close to Beach
Priced at June ('25 - 25) $20,000, July ('25 - 25) $28,000; August ('25 - 25) $33,000 Beds: 3 Baths: 2 Sq. Feet: 1456Rental Registration# 2023-L-0027. Located within close proximity to sandy beach with sunsets galore ... Property Details
Bayview Contemporary Shelter Island
Priced at Winter (01/01/25 - 06/02/25) $6,000; Custom (06/03/25 - 06/16/25) $9,000; Custom (06/17/25 - 06/30/25) $10,000; July ('25 - 25) $21,000; Two Weeks (07/01/25 - 07/14/25) $11,000; Custom (07/15/25 - 07/31/25) $12,500; Two Weeks (08/01/25 - 08/31/25) $13,500; Two Weeks (08/01/25 - 09/06/25) $13,500; August(LD) ('25 - 25) $26,000; September ('25 - 25) $16,000; Weekly (09/06/25 - 06/04/26) $5,500 Beds: 4 Baths: 3 Sq. Feet: 2600Rental Registration #2025-V-002. This sunny Contemporary with slices of water views has loads of ... Property Details
Iconic Shelter Island Heights Waterview Victorian
Priced at July ('25 - 25) $36,000; July/August(LD) ('25 - 25) $80,000; August(LD) ('25 - 25) $45,000 Beds: 5 Baths: 3.5 Sq. Feet: 2596Rental Registration #2023-L-0145. Since the turn of the century, this Victorian has greeted visitors ... Property Details
Shelter Island Spacious Traditional with Pool Close to Beach
Priced at Custom (07/19/25 - 07/26/25) $10,900; Custom (09/17/25 - 09/30/25) $21,000; October ('25 - 25) $31,000 Beds: 5 Baths: 3.5 Sq. Feet: 2552Rental Registration #2023-V-0039 & 2023-L-0133. Enjoy your summer at this spacious traditional ... Property Details
Cheery Renovated Shelter Island Farmhouse near Marina
Priced at Year Round (10/01/25 - 09/30/26) $62,000; August(LD) ('25 - 25) $15,000 Beds: 4 Baths: 2.5 Sq. Feet: 2052Rental Registration #2023-L-0172 & 2024-V-0023. This sun filled farmhouse has been recently ... Property Details
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
Wades Beach Chic Cottage on the Dunes
Priced at June ('25 - 25) $25,000; Custom (06/01/25 - 09/01/25) $95,000; July ('25 - 25) $40,000; August ('25 - 25) $45,000 Beds: 3 Baths: 2 Sq. Feet: 1080Rental Registration #2024-L-0015. This fresh and chic beach cottage promises a fun summer on the ... 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
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 June/July ('25 - 25) $65,000; July ('25 - 25) $35,000 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
Shelter Island Pristine Traditional with Pool
Priced at July (07/01/25 - 07/18/25) $20,000; August(LD) ('25 - 25) $37,000 Beds: 4 Baths: 3 Sq. Feet: 3194Rental Registration #2024-L-0027. This recently built traditional is located on one acre within ... 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
