Rental Listings
Cozy 2 Bedroom Cottage
Priced at Winter (01/01/23 - 03/31/23) $12,000; Custom (04/01/23 - 04/21/23) $6,750; August ('23 - 23) $35,000 Beds: 2 Baths: 1 Sq. Feet: 1248Rental Registration #2022-L-0011. 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 February ('23 - 23) $10,000; March ('23 - 23) $10,000; April ('23 - 23) $12,000; May ('23 - 23) $18,000; Custom (06/15/23 - 06/22/23) $6,000; Custom (08/18/23 - 09/04/23) $32,000; September ('23 - 23) $20,000; Custom (09/18/23 - 09/30/23) $12,000; October ('23 - 23) $18,000; November ('23 - 23) $15,000; December ('23 - 23) $15,000 Beds: 5 Baths: 6.5 Sq. Feet: 5670Rental Registration #2021-L-88. This charming 5 bedroom, 6 bath colonial has an open floor plan that ... Property Details
Shelter Island Hidden Gem with Pool
Priced at August(LD) ('23 - 23, w/o LD $27k) $30,000 Beds: 4 Baths: 3 Sq. Feet: 1542Rental Registration #2022-L-0013. This modern 4 Bedroom, 3 bathroom hidden gem with pool features an ... Property Details
Shelter Island Quiet Contemporary with Pool
Priced at Weekly (06/01/23 - 06/30/23) $7,000; Weekly (07/01/23 - 07/31/23) $8,750; Weekly (08/23/23 - 08/31/23) $10,000; Custom (08/23/23 - 09/04/23) $15,000 Beds: 4 Baths: 3 Sq. Feet: 1900Rental Registration #2021-L-72. Located within close proximity to Wades Beach on Shelter Island, ... Property Details
Shelter Island Harborfront Farmhouse
Priced at June ('23 - 23) $15,000; July ('23 - 23) $30,000 RENTED; August(LD) ('23 - 23) $35,000 RENTED; Weekly (09/05/23 - 09/30/23) $5,500; September (09/05/23 - 09/30/23) $16,500 Beds: 3 Baths: 1 Full, 1 Half Sq. Feet: 1536Rental Registration #2121-L-54. This classic Shelter Island harborfront farmhouse was built in 1900 ... Property Details
Shelter Island Heights Charming Waterview Farmhouse
Priced at June ('23 - 23) $15,000; July ('23 - 23) $28,000; August(LD) ('23 - 23) $32,000 Beds: 4 Baths: 2 Sq. Feet: 2007Rental Registration #2021-L-55. New to the rental market! This Shelter Island Heights farmhouse, ... Property Details
Shelter Island Serenity with Farm Views and Saltwater Pool
Priced at July ('23 - 23) $29,000 Beds: 3 Baths: 2 Sq. Feet: 1639Rental Registration #2021-L-22. Bordering Westmoreland Farm, this spacious traditional with privet ... Property Details
Sunny Shelter Island Cape Cod
Priced at June ('23 - 23) $12,000; August(LD) ('23 - 23) $22,000 Beds: 5 Baths: 2 Sq. Feet: 1779Rental Registration #2021-L-43. This pristine five bedroom Cape Cod was recently renovated and is ... Property Details
Modernist Waterfront with Pool near Shelter Island Heights
Priced at July ('23 - 23) $50,000 Beds: 3 Baths: 3.5 Sq. Feet: 1536Rental Registration #2021-L-28. Tucked away on a gravel road, just outside Shelter Island Heights, ... Property Details
Shelter Island Mid Century Modern with Pool
Priced at September ('23 - 23) $16,000; Winter (09/01/23 - 05/31/24) $4,200; October ('23 - 23) $16,000 Beds: 3 Baths: 2.5 Sq. Feet: 1634Rental Registration# 21-1-64.This sleek mid century modern on shy acre is located a few doors from a ... Property Details
Shelter Island Cottage with Pool Close to Beach
Priced at June ('23 - 23) $15,000; July ('23 - 23) $30,000; August(LD) ('23 - 23, w/o LD $33k) $37,000 Beds: 3 Baths: 2 Sq. Feet: 1456Rental Registration# 2021-L-41. Located within close proximity to sandy beach with sunsets galore ... Property Details
Bayview Contemporary Shelter Island
Priced at Weekly (09/06/22 - 06/04/23) $5,000; Custom (06/13/23 - 06/23/23) $9,000; July ('23 - 23) $20,900; Two Weeks (07/01/23 - 07/14/23) $11,000; August(LD) ('23 - 23) $24,000; Two Weeks (08/01/23 - 09/04/23) $13,000 Beds: 4 Baths: 3 Sq. Feet: 2600Rental Registration #2022-V-0017. This sunny Contemporary with slices of water views has loads of ... Property Details
Iconic Shelter Island Heights Waterview Victorian
Priced at Custom (05/26/23 - 06/30/23) $26,000; June ('23 - 23) $23,000; July ('23 - 23) $31,000; August(LD) ('23 - 23, w/o LD $34k) $36,000; Custom (09/04/23 - 09/30/23) $26,000 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
Charming and Simple Harborfront with Dock
Priced at May ('23 - 23) $10,000; Custom (06/01/23 - 06/15/23) $10,000; Custom (07/15/23 - 08/15/23) $35,000; Custom (09/18/23 - 09/30/23) $10,000; October ('23 - 23) $20,000 Beds: 4 Baths: 2 Sq. Feet: 2170Rental Registration #2023-L-0009. This straightforward L-shaped cottage on the harbor has a ... Property Details
Iconic Shelter Island Heights Waterview Victorian
Priced at June ('23 - 23) $32,000; July ('23 - 23) $38,000; August(LD) ('23 - 23, w/o LD $40k) $42,000 Beds: 5 Baths: 3 Full, 2 Half Sq. Feet: 2740Rental Registration #20-L-0095. This completely restored 1890's Shelter Island Victorian is in the ... Property Details
Shelter Island Cottage with Beach, Dock & Mooring
Priced at June/July (05/26/23 - 07/31/23) $70,000; July ('23 - 23) $40,000 Beds: 4 Baths: 4 Sq. Feet: 2180Rental Registration# 2022-L-0112. Located on the harbor, this cheery country cottage has wonderful ... Property Details
Shelter Island Spacious Traditional with Pool Close to Beach
Priced at Custom (07/15/23 - 07/31/23) $22,000; August(LD) ('23 - 23, w/o LD $50k ) $62,500; Two Weeks (09/05/23 - 09/30/23) $18,000 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
Newly renovated 1911 Plantation Style Home
Priced at May ('23 - 23) $30,000; June ('23 - 23) $35,000; July ('23 - 23) $50,000; August(LD) ('23 - 23) $65,000 Beds: 6 Baths: 4.5 Sq. Feet: 2790Rental Registration #2023-L-0005. This newly renovated 1911 plantation style home combines old world ... Property Details
Glorious Shelter Island Waterview with Pool
Priced at Winter (10/01/22 - 04/30/23) $10,000; Custom (05/01/23 - 05/25/23) $25,000; MD-LD ('23 - 23) $150,000; June ('23 - 23) $35,000; July ('23 - 23) $50,000; August(LD) ('23 - 23) $60,000; Custom (09/05/23 - 09/30/23) $25,000 Beds: 4 Baths: 3 Sq. Feet: 2337Rental Registration #19L-0077 This elevated contemporary sited on one acre overlooking the waters ... Property Details
Shelter Island Spacious Traditional with Pool
Priced at Feb ('23 - 23) $15,000; March ('23 - 23) $15,000; April ('23 - 23) $15,000; May ('23 - 23) $15,000; June ('23 - 23) $45,000; July ('23 - 23) $55,000; August ('23 - 23) $65,000; October ('23 - 23) $15,000; November ('23 - 23) $15,000; 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
