Rental Listings
Shelter Island Cape Code with Deeded Waterfront Access
Priced at June ('25 - 25) $15,000; July ('25 - 25) $20,000; August(LD) ('25 - 25) $25,000 Beds: 5 Baths: 4 Sq. Feet: 3128Rental Registration #2024-L-0099. This Shelter Island Cape Cod, located in Menantic Peninsula on a ... Property Details
Glorious Shelter Island Waterfront Cottage
Priced at MD-LD ('25 - 25) $100,000; June ('25 - 25) $25,000; July/August(LD) ('25 - 25) $80,000; July ('25 - 25) $40,000; August(LD) ('25 - 25, w/o LD $42k) $43,000 Beds: 4 Baths: 2 Sq. Feet: 1755Rental Registration #2023-L-0071. This beachfront four bedroom with 3 Queen sized beds and one full ... Property Details
Shelter Island Sunny Wades Beach Contemporary
Priced at MD-LD (05/24/25 - 09/02/25) $55,000; July/August(LD) ('25 - 25) $46,000; Two Weeks (07/01/25 - 07/31/25) $13,000; July ('25 - 25) $22,000; August ('25 - 25) $23,000 Beds: 3 Baths: 2.5 Sq. Feet: 2428Rental Registration #2024-L-0076. Located a stone's throw from popular southerly beach in quiet ... Property Details
Shelter Island Elegant Bayfront with Deepwater Dock
Priced at 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 Traditional with Pool, Beach and Lighthouse Views
Priced at July ('25 - 25) $69,000; August(LD) ('25 - 25) $80,000 Beds: 4 Baths: 4.5 Sq. Feet: 5122Rental Registration #2024-L-0049. This traditional, with inspiring views of "Bug Light" lighthouse ... Property Details
Shelter Island Newly Renovated Water View Cottage with Pool
Priced at January ('25 - 25) $5,000; February ('25 - 25) $5,000; March ('25 - 25) $5,000; April ('25 - 25) $7,500; May ('25 - 25) $10,000; June ('25 - 25) $15,000; July/August ('25 - 25) $95,000; July ('25 - 25) $45,000; Custom (7/15/25 - 09/01/25) $75,000; August(LD) ('25 - 25) $55,000; September ('25 - 25) $25,000 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 MD-LD ('25 - 25) $70,000; June ('25 - 25) $10,500; July ('25 - 25) $15,000; July/August(LD) ('25 - 25) $45,000; August(LD) ('25 - 25, w/o LD $25k) $30,000 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 Heights Renovated Apartment
Priced at Year Round (12/01/24 - 11/30/25) $42,000 Beds: 2 Baths: 1Located in the heart of Shelter Island Heights in a mixed use building, this newly renovated 2 ... Property Details
Shelter Island Sweet Cottage with Pool
Priced at MD-LD ('25 - 25) $29,500; June ('25 - 25) $8,500; July ('25 - 25) $10,000; August(LD) ('25 - 25) $12,000 Beds: 2 Baths: 2 Sq. Feet: 888Rental Registration #2023-L-0119. Located a stone's throw from the beach, farm stand, town and ... Property Details
1887 Dering Harbor Village Victorian with Pool and Dock
Priced at May (05/01/25 - 05/28/25) $20,000 RENTED; June (05/30/25 - 06/30/25) $25,000 RENTED; 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
Gracious Shelter Island with Pool
Priced at November ('24 - 24) $4,000; December ('24 - 24) $4,000; January ('25 - 25) $4,000; February ('25 - 25) $4,000; March ('25 - 25) $4,000; April ('25 - 25) $4,000 Beds: 5 Baths: 2Rental Registration #2023-L-0171. This classic Shelter Island country home was recently renovated by ... Property Details
Charming Shelter Island Heights Harborview Victorian
Priced at Two Weeks (06/01/25 - 06/30/25) $10,000; Two Weeks (07/01/25 - 07/31/25) $10,000; Two Weeks (08/01/25 - 08/31/25) $12,000 Beds: 4 Baths: 2.5 Sq. Feet: 2140Rental Registration #2022-L-0075. This 1885 Shelter Island Heights Victorian, located in the heart ... Property Details
Cozy 2 Bedroom Cottage
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
5 Bedroom Colonial with Infinity Pool and Waterfront Beach
Priced at 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
Bayview Contemporary Shelter Island
Priced at Weekly (01/01/25 - 06/02/25) $5,500; Custom (06/03/25 - 06/16/25) $10,000; Custom (06/17/25 - 06/30/25) $10,000; Two Weeks (07/01/25 - 07/14/25) $12,000; Custom (07/15/25 - 07/31/25) $12,500; August(LD) ('25 - 25) $26,000; Two Weeks (08/01/25 - 09/01/25) $16,000 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 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
Cheery Renovated Shelter Island Farmhouse near Marina
Priced at Year Round (10/01/24 - 09/30/25) $62,000; July ('25 - 25) $12,000; July/August(LD) ('25 - 25) $25,000; August(LD) ('25 - 25) $15,000 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 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
Shelter Island Expanded Cottage with Pool
Priced at June ('25 - 25) $18,000; Two Weeks (06/01/25 - 06/30/25) $10,000; Two Weeks (07/01/25 - 09/01/25) $14,000; July ('25 - 25) $26,000; August(LD) ('25 - 25) $26,000 Beds: 3 Baths: 3 Sq. Feet: 1933Rental Registration #2023-V-0003. Located within close proximity of association beaches, this ... 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
