Rental Listings
Wades Beach Traditional
Priced at July ('23 - 23) $21,000; Custom (07/29/23 - 08/12/23) $10,000; Custom (08/19/23 - 09/04/23) $12,000 Beds: 3 Baths: 2 Sq. Feet: 1345Rental Registration #2022-L-0032. Located on a shy acre within a stone's throw of Wades Beach, this ... Property Details
Shelter Island Scandinavian with Pool and Guest House
Priced at July ('23 -23) $35,000 RENTED; August ('23 - 23) $40,000 RENTED Beds: 5 Baths: 4 Sq. Feet: 3600Rental Registration #2022-L-0045. Located within close proximity to popular Sunset Beach, golf, ... Property Details
Shelter Island Quintessential Beach House
Priced at June ('23 - 23) $22,000 RENTED; Custom (07/15/23 - 07/29/23) $6,500; August(LD) ('23 - 23) $34,100 RENTED; Custom (09/02/23 - 09/13/23) $4,000; Weekly (09/21/23 - 09/30/23) $3,500; Weekly (10/01/23 - 04/30/24) $2,625; Custom (10/01/23 - 04/30/24) $10,000 Beds: 4 Baths: 2 Sq. Feet: 2406Rental Registration #2022-L-0040. This distinctive beach house is what summer on Shelter Island is ... Property Details
Chic Shelter Island Barn with Pool and Day Dock
Priced at July ('23 - 23) $27,000 RENTED; August(LD) ('23 -23, w/o LD $27k) $33,000 Beds: 3 Baths: 2 Sq. Feet: 1560Rental Registration #2021-L-85. This chic barn-style house is located off a quiet lane and is ready ... Property Details
Sun-Filled Shelter Island Charming Cottage Close to Beach
Priced at Custom (05/26/23 - 07/31/23) $28,000; Custom (05/26/23 - 06/30/23) $14,000; June ('23 - 23) $12,000; July ('23 - 23) $14,000; August ('23 - 23) $14,000 RENTED; September (09/05/23 - 09/30/23) $12,000; Custom (09/05/23 - 09/10/23) $2,000 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 Custom (08/03/23 - 09/30/23) $12,000 RENTED; October ('23 - 23) $7,000 RENTED; November ('23 - 23) $6,000 RENTED Beds: 3 Baths: 2 Sq. Feet: 1636Rental Registration #2021-L-112. This clean and sweet cottage has recently been renovated and is ... Property Details
Cozy 2 Bedroom Cottage
Priced at August ('23 - 23) $35,000 RENTED; Winter (11/01/23 - 03/31/24) $4,000 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 Custom (06/15/23 - 06/22/23) $6,000; Custom (08/18/23 - 09/04/23) $32,000; September (09/01/23 - 09/17/23) $11,000; Custom (09/18/23 - 09/30/23) $12,000 RENTED; October ('23 - 23) $18,000 RENTED; November ('23 - 23) $15,000; 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 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 Resort Style Retreat with Pool near Beach
Priced at Custom (06/26/23 - 07/28/23) $42,500 Beds: 3 Baths: 2 Sq. Feet: 1543Rental Registration #2023-L-0069. New to the rental market! This Shelter Island retreat with an ... 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; Custom (09/05/23 - 09/30/23) $16,500; Custom (09/07/23 - 09/21/23) $9,000 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 #2023-L-0016. Bordering Westmoreland Farm, this spacious traditional with privet ... Property Details
Sunny Shelter Island Cape Cod
Priced at Custom (05/19/23 - 06/21/23) $14,153; July ('23 - 23) $15,000 RENTED; Weekly (08/07/23 - 09/04/23) $5,000; Custom (08/07/23 - 09/05/23) $25,833 Beds: 5 Baths: 2 Sq. Feet: 1779Rental Registration #2023-L-0032. 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 Artist’s Stylish Retreat
Priced at Two Weeks (08/18/23 - 08/31/23) $10,000 Beds: 2 Baths: 2.5 Sq. Feet: 1922Rental Registration #2021-00-03. Located a stone's throw from Wades Beach and sited off the road in ... 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 Retreat with Pool Close to Beach
Priced at July ('23 - 23) $27,000; August(LD) ('23 - 23, w/o LD $30k) $35,000 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 Custom (06/01/23 - 06/12/23) $7,800; Custom (06/13/23 - 06/23/23) $9,000 RENTED; Two Weeks (07/01/23 - 07/14/23) $11,000 RENTED; July (07/18/23 - 07/31/23) $11,500; August(LD) ('23 - 23) $24,000; Two Weeks (08/01/23 - 09/06/23) $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 (07/18/23 - 07/30/23) $12,000; August(LD) ('23 - 23, w/o LD $34k) $36,000 RENTED; 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
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