Rental Listings
Shelter Island Nantucket Style Farmhouse with Dock and Sunsets
Priced at Custom (07/01/25 - 07/24/25) $45,000 Beds: 4 Baths: 3.5 Sq. Feet: 2799Rental Registration #2025-L-0013. This picturesque Nantucket style farmhouse is tucked away in ... Property Details
Shelter Island Cape Code with Deeded Waterfront Access
Priced at 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 Two Weeks (08/16/25 - 09/01/25) $22,000 Beds: 4 Baths: 2 Sq. Feet: 1755Rental Registration #2025-L-0011. This beachfront four bedroom with 3 Queen sized beds and one full ... Property Details
Shelter Island Sunny Wades Beach Contemporary
Priced at Custom (07/01/25 - 07/30/25) $20,000; Two Weeks (07/01/25 - 07/15/25) $13,000; Two Weeks (07/17/25 - 07/31/25) $12,500; Custom (09/03/25 - 09/30/25) $3,000; Custom (10/03/25 - 10/31/25) $2,700; Custom (11/02/25 - 11/30/25) $2,700 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 July/August(LD) ('25 - 25) $100,000 RENTED 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 MD-LD ('25 - 25) $95,000; July/August(LD) ('25 - 25) $80,000; July ('25 - 25) $40,000; Custom (7/15/25 - 09/01/25) $65,000; Two Weeks (08/01/25 - 08/15/25) $20,000; August(LD) ('25 - 25) $45,000; September ('25 - 25) $20,000; October ('25 - 25) $12,500; November ('25 - 25) $5,000; December ('25 - 25) $5,000; January ('26 - 26) $5,000; February ('26 - 26) $5,000; March ('26 - 26) $5,000 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 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 Picturesque Farmhouse with Pool
Priced at July ('25 - 25) $25,000 RENTED Beds: 8 Baths: 3 Sq. Feet: 2720Rental Registration #2025-L-0014. Located a short distance from Heights, ferry, shops, fine dining ... Property Details
Shelter Island Beach Cottage
Priced at MD-LD ('25 - 25) $32,000; July ('25 - 25) $11,000; August ('25 - 25) $12,000 Beds: 3 Baths: 2 Sq. Feet: 1428Rental Registration #2025-L-0007. Shelter island's south side offers expansive Shell Beach and ... Property Details
Shelter Island Estate Home Bordering Golf Course
Priced at July ('25 - 25) $45,000 RENTED; August(LD) ('25 - 25) $50,000 RENTED Beds: 4 Baths: 5.5 Sq. Feet: 4000Rental Registation #2025-L-0004. This new estate home on a shy acre bordering Gardiners Bay Country ... Property Details
Shelter Island Traditional with Pool bordering Preserve
Priced at Weekly (08/15/25 - 09/01/25) $19,500; Weekly (09/01/25 - 09/30/25) $12,900; Weekly (10/01/25 - 10/31/25) $6,900; Weekly (11/01/25 - 11/30/25) $5,500; Weekly (12/01/25 - 12/31/25) $5,000 Beds: 5 Baths: 5.5 Sq. Feet: 4700Rental Registration #2024-V-0024. This grand compound bordering parkland is spectacular. The main ... Property Details
Shelter Island Close Proximity to Beach
Priced at Two Weeks (07/01/25 - 07/31/25) $11,000; Weekly (07/01/25 - 07/31/25) $5,500; Two Weeks (08/01/25 - 09/02/25) $11,000; Weekly (08/01/25 - 08/31/25) $5,500 Beds: 3 Baths: 2 Sq. Feet: 1384Rental Registration #2025-V-011. Welcome to a charming and immaculate cottage that is sure to ... Property Details
Shelter Island Modern with Pool
Priced at Custom (07/01/25 - 07/13/25) $25,000; August(LD) ('25 - 25) $45,000 RENTED Beds: 3 Baths: 3 Sq. Feet: 2891Rental Registration #2023-L-0161. This sleek and sun-filled modern on approximately one acre borders ... Property Details
Shelter Island Wades Beach with Pool
Priced at July ('25 - 25) $32,000; August(LD) ('25 - 25) $35,000 Beds: 4 Baths: 3 Sq. Feet: 2842Rental Registration #2023-L-0163. This arts and crafts cottage sits on 1.0+/- acre overlooking a ... Property Details
Shelter Island Charming Harbor Front Cottage
Priced at July ('25 - 25) $25,000; August(LD) ('25 - 25) $25,000 Beds: 3 Baths: 3 Sq. Feet: 2209Rental Registration #2023-L-0164. Turn of the century cottage with southern views onto the harbor ... Property Details
Charming Shelter Island Heights Harborview Victorian
Priced at Two Weeks (07/01/25 - 07/21/25) $10,000 Beds: 4 Baths: 2.5 Sq. Feet: 2140Rental Registration #2024-L-0110. This 1885 Shelter Island Heights Victorian, located in the heart ... Property Details
Shelter Island Scandinavian with Pool and Guest House
Priced at July ('25 -25) $32,000; Two Weeks (08/01/25 - 08/15/25) $15,000 RENTED Beds: 5 Baths: 4 Sq. Feet: 3600Rental Registration #2024-L-0043. Located within close proximity to popular Sunset Beach, golf, ... Property Details
Chic Shelter Island Barn with Pool and Day Dock
Priced at Custom (08/25/25 - 09/05/25) $11,000 Beds: 3 Baths: 2 Sq. Feet: 1560Rental Registration #2025-L-0006. This chic barn-style house is located off a quiet lane and is ... Property Details
Sun-Filled Shelter Island Charming Cottage Close to Beach
Priced at August(LD) ('25 - 25) $14,000 RENTED Beds: 4 Baths: 3 Sq. Feet: 2400Rental Registration #2024-L-0026. This sun filled one level cottage is located within a stone's ... Property Details
