Rental Listings
Quiet Shelter Island Traditional with Pool
Priced at May ('24 - 24) $20,000; Custom (06/01/24 - 06/22/24) $30,000; Custom (07/01/24 - 07/07/24) $10,000; Custom (07/16/24 - 07/25/24) $13,500; August(LD) ('24 - 24) $45,000 Beds: 4 Baths: 3.5 Sq. Feet: 3115Rental Registration #2022-L-0046. This traditional, sited on 1+/- acre, is located on a quiet ... Property Details
Shelter Island Contemporary with Pool and Association Beach
Priced at Extended Season (10/02/23 - 05/27/24) $2,000; June ('24 - 24) $20,000; July ('24 - 24) $28,000; August(LD) ('24 - 24) $30,000 Beds: 4 Baths: 2 Sq. Feet: 1604Rental Registration #2021-L-114. New to the market! Completely refreshed in Spring of 2022, this ... Property Details
Shelter Island Quintessential Beach House
Priced at Custom (10/01/23 - 12/6/23) $10,000 RENTED; Weekly (05/01/24 - 05/31/24) $3,800; May ('24 - 24) $13,800; June (06/01/24 - 06/14/24) $11,000; Custom (07/01/24 - 07/31/24) $31,000; August(LD) ('24 - 24) $35,100; Custom (09/01/24 - 09/24/24) $18,000 Beds: 4 Baths: 2 Sq. Feet: 2406Rental Registration #2022-L-0040. This distinctive beach house is what summer on Shelter Island is ... Property Details
Spacious Traditional with Pool on Shelter Island
Priced at May ('24 -24) $10,000; Custom (06/01/24 - 06/30/24) $30,000; July ('24 - 24) $45,000; August(LD) ('24 -24) $60,000 Beds: 4 Baths: 3.5 Sq. Feet: 5353Rental Registration #2021-L-116. This spacious traditional sits on one acre and has over 5300sf of ... Property Details
Sun-Filled Shelter Island Charming Cottage Close to Beach
Priced at June ('24 - 24) $12,000; July ('24 - 24) $14,000; August ('24 - 24) $14,000; September (09/03/24 - 09/30/24) $12,000 Beds: 4 Baths: 3 Sq. Feet: 2400Rental Registration #2022-L-0111. This sun filled one level cottage is located within a stone's ... Property Details
Shelter Island Renovated Cottage near Beach
Priced at Weekly (05/01/24 - 09/04/24) $3,500; Custom (05/01/24 - 05/22/24) $10,500; MD-LD ('24 - 24) $39,000; Custom (05/24/24 - 06/27/24) $17,500; Custom (06/29/24 - 07/30/24) $16,000; August(LD) ('24 - 24) $17,000 Beds: 3 Baths: 2 Sq. Feet: 1636Rental Registration #2023-L-0141. This clean and sweet cottage has recently been renovated and is ... Property Details
Cozy 2 Bedroom Cottage
Priced at Winter (11/01/23 - 03/31/24) $4,000; Custom (04/01/24 - 04/21/24) $6,750; August ('24 - 24) $35,000 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
5 Bedroom Colonial with Infinity Pool and Waterfront Beach
Priced at December ('23 - 23) $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 Retreat with Pool Close to Beach
Priced at MD-LD ('24 - 24) $60,000; June ('24 - 24) $15,000; July/August(LD) ('24 - 24) $45,000; July ('24 - 24) $20,000; August(LD) ('24 - 24, w/o LD $25k) $28,000 Beds: 3 Baths: 2 Sq. Feet: 1456Rental Registration# 2023-L-0027. Located within close proximity to sandy beach with sunsets galore ... Property Details
Iconic Shelter Island Heights Waterview Victorian
Priced at Custom (05/27/24 - 06/30/24) $26,000; June ('24 - 24) $23,000; July ('24 - 24) $29,000; August(LD) ('24 - 24, w/o LD $34k) $36,000 Beds: 5 Baths: 3.5 Sq. Feet: 2596Rental Registration #2022-S-0002. 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 (05/24/24 - 06/30/24) $27,000; MD-LD ('24 - 24) $110,000; July/August(LD) ('24 - 24) $90,000; July ('24 - 24) $45,000; August(LD) ('24 - 24, w/o LD $45k) $47,000 Beds: 5 Baths: 3.5 Sq. Feet: 2552Rental Registration #2022-L-0048. Enjoy your summer at this spacious traditional with plenty of room ... Property Details
Cheery Renovated Shelter Island Farmhouse near Marina
Priced at Year Round (09/01/23 - 08/31/24) $72,000 Beds: 4 Baths: 2.5 Sq. Feet: 2052Rental Registration #2021-S-0016 This sun filled farmhouse has been recently renovated and boasts an ... Property Details
Montclair Colony Shelter Island
Priced at June ('24 - 24) $7,500; July ('24 - 24) $8,500; August(LD) ('24 - 24) $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
Newly renovated 1911 Plantation Style Home
Priced at June ('24 - 24) $30,000; July ('24 - 24) $40,000; August(LD) ('24 - 24) $50,000 Beds: 6 Baths: 4.5 Sq. Feet: 2790Rental Registration #2023-L-0005. This newly renovated 1911 plantation style home combines old world ... Property Details
Shelter Island Spacious Traditional with Pool
Priced at December ('23 - 23) $15,000 Beds: 5 Baths: 5.5 Sq. Feet: 3868Rental Registration #2023-L-0003. With views to a 12 +/- acre preserve directly across the street ... Property Details
Shelter Island Close Proximity to Everything
Priced at July ('24 - 24) $13,000; August ('24 - 24) $14,000; September (09/03/24 - 09/30/24) $9,500 Beds: 3 Baths: 1 Sq. Feet: 1600Rental Registration# 19L-2133. This fresh and updated upside down modern on .75 acre is located ... Property Details
Shelter Island Beach House with Pool
Priced at MD-LD ('24 - 24) $60,000; June ('24 - 24) $15,000; July/August ('24 - 24) $52,000; July ('24 - 24) $25,000; August(LD) ('24 - 24) $30,000 Beds: 3 Baths: 2 Sq. Feet: 1424Rental Registration #2023-L-0001. Enjoy your summer stay at this pristine Shelter Island 3 bedroom, ... Property Details
Shelter Island Sleek and Chic Waterfront
Priced at June/July (05/24/24 - 07/31/24) $90,000; June (05/24/24 - 06/30/24) $40,000 Beds: 4 Baths: 2.5 Sq. Feet: 3091Rental Registration #2023-L-0066. This resort-style waterfront modern offers everything you could ... Property Details
Shelter Island Sleek with Pool
Priced at May ('24 - 24) $15,000; June ('24 - 24) $15,000; July ('24 - 24) $35,000; July/August(LD) ('24 - 24) $70,000; August(LD) ('24 - 24) $35,000 Beds: 3 Baths: 3 Sq. Feet: 1300Rental Registration #2022-L-0074. Located within close proximity to sandy beach, this recently ... Property Details
Wades Beach Chic Cottage on the Dunes
Priced at Year Round (11/01/23 - 10/31/24) $120,000 Beds: 3 Baths: 2 Sq. Feet: 1080Rental Registration #2022-L-0067. This fresh and chic beach cottage promises a fun summer on the ... Property Details
