Rental Listings
Shelter Island Historic Cottage Close to Beach
Priced at MD-LD ('26 - 26) $35,000; June ('26 - 26) $8,000; July/August(LD) ('26 - 26) $33,000; July ('26 - 26) $15,000; August(LD) ('26 - 26) $22,000 Beds: 2 Baths: 1 Sq. Feet: 1255Rental Registration #2026-L-0041. Located within close proximity to popular beachfront, golf course, ... Property Details
Shelter Island Close Proximity to Beach
Priced at Custom (06/15/26 - 06/30/26) $11,000; July ('26 - 26) $26,000; July/August(LD) ('26 - 26) $56,000; August(LD) ('26 - 26, w/o LD $28k) $34,000 Beds: 3 Baths: 2.5Rental Registration #2026-L-0026. This recently built home sits on 1.43 and exudes a hand crafted ... Property Details
Shelter Island Harborview Cottage
Priced at July ('26 - 26) $27,000; August(LD) ('26 - 26, w/o LD $29k) $32,000 Beds: 5 Baths: 3 Sq. Feet: 1248Rental Registration #2026-L-0012. Located on a quiet lane on Ram Island, with views toward Coecles ... Property Details
Timeless Charm on Shelter Island
Priced at July ('26 - 26) $16,000; August ('26 - 26) $18,000 Beds: 4 Baths: 2.5 Sq. Feet: 1566Rental Registration # 2026-L-0031. Nestled on a quiet, tree-lined street, this beautifully preserved ... Property Details
Shelter Island Waterview Cottage
Priced at June ('26 - 26) $18,000; July ('26 - 26) $25,000; August ('26 - 26) $30,000; September ('26 - 26) $20,000 Beds: 4 Baths: 3.5 Sq. Feet: 2675Rental Registration #2026-L-0028. Set on a peaceful 0.75-acre property in the heart of Shelter ... Property Details
Turn-Key Shelter Island Water View Traditional with Pool
Priced at Two Weeks (05/26/26 - 06/28/26) $17,500; July ('26 - 26) $40,000 RENTED; August(LD) ('26 - 26, w/o LD $48k) $60,000 Beds: 4 Baths: 3Rental Registration #2025-L-0115. If you are seeking a turn-key rental, new to the market, with room ... Property Details
Shelter Island Farmhouse with Pool
Priced at Weekly (07/15/26 - 07/22/26) $9,000 RENTED Beds: 4 Baths: 3.5 Sq. Feet: 2554Rental Registration # 2025-L-0043. Located within close proximity to harbor and beach, this ... Property Details
Shelter Island Modern A-Frame with Pool and Cabana
Priced at July ('26 - 26) $27,100; August(LD) ('26 - 26) $31,000 RENTED Beds: 3 Baths: 2 Sq. Feet: 1190Rental Registration #2025-L-0052. This chic and sunny 3 bedroom and 2 bath A-frame, perched on a ... Property Details
Shelter Island Nantucket Style Farmhouse with Dock and Sunsets
Priced at June ('26 - 26) $20,000; Custom (07/01/26 - 07/25/26) $40,000 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 June ('26 - 26) $15,000; July ('26 - 26) $20,000; August(LD) ('26 - 26, w/o LD $25k) $28,000 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 June ('26 - 26) $25,000 RENTED; Two Weeks (06/01/26 - 06/14/26) $14,000 RENTED; July ('26 - 26) $40,000 RENTED; Two Weeks (07/01/26 - 07/14/26) $25,000 RENTED; Custom (07/15/26 - 08/02/26) $25,000 RENTED; August(LD) ('26 - 26, w/o LD $42k) $47,000 RENTED 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 Elegant Bayfront with Deepwater Dock
Priced at July ('26 - 26) $44,000; Two Weeks (07/01/26 - 07/31/26) $22,000; August ('26 - 26) $50,000; Two Weeks (08/01/26 - 08/31/26) $24,000 Beds: 5 Baths: 4.5 Sq. Feet: 4467Rental Registration #2026-L-0005. First offering! This elegant traditional graces a slight bluff ... Property Details
Shelter Island Traditional with Pool, Beach and Lighthouse Views
Priced at MD-LD ('26 - 26) $145,000 RENTED; July ('26 - 26) $55,000 RENTED; August(LD) ('26 - 26, w/o LD $65k) $70,000 RENTED Beds: 4 Baths: 4.5 Sq. Feet: 5122Rental Registration #2025-L-0133. This traditional, with inspiring views of "Bug Light" lighthouse ... Property Details
Shelter Island Newly Renovated Water View Cottage with Pool
Priced at MD-LD ('26 - 26) $115,000; June ('26 - 26) $25,000; Two Weeks (07/01/26 - 07/15/26) $27,500; July/August (LD) ('26 - 26) $100,000; July ('26 - 26) $50,000; Custom (07/15/26 - 08/15/26) $50,000; Custom (07/15/26 - 09/07/26) $78,000; Two Weeks (07/16/26 - 07/31/26) $27,500; August(LD) ('26 - 26) $55,000; Two Weeks (08/01/26 - 08/15/26) $30,000; Two Weeks (08/16/26 - 08/31/26) $30,000; September ('26 - 26) $25,000; October ('26 - 26) $15,000; November ('26 - 26) $7,500; December ('26 - 26) $7,500 Beds: 3 Baths: 3.5 Sq. Feet: 1836Rental Registration #2026-L-0004. Located on a private Ram Island lane, this stylish and uplifting ... Property Details
Shelter Island Sweet Cottage with Pool
Priced at August(LD) ('26 - 26) $20,000 Beds: 2 Baths: 2 Sq. Feet: 888Rental Registration #2024-L-0126. Located a stone's throw from the beach, farm stand, town and ... Property Details
Shelter Island Picturesque Farmhouse with Pool
Priced at July ('26 - 26) $30,000 RENTED Beds: 8 Baths: 3 Sq. Feet: 2720Rental Registration #2025-L-0014. Located a short distance from Heights, ferry, shops, fine dining ... Property Details
Charming Cottage
Priced at Custom (08/10/26 - 09/08/26) $18,000 Beds: 2 Baths: 1 Sq. Feet: 1000Rental Registration #2025-L-0053. Located within close proximity to popular beaches, this two ... Property Details
Sweet and Sunny Shelter Island with Pool
Priced at July ('26 - 26) $45,000; August(LD) ('26 - 26, w/o LD $50k) $55,000 Beds: 4 Baths: 3.5 Sq. Feet: 3053Rental Registration #2025-V-0026. This pristine, sun-filled Shelter Island traditional, set on a shy ... Property Details
Shelter Island Traditional with Pool bordering Preserve
Priced at June ('26 - 26) $60,000; July ('26 - 26) $75,000; August ('26 -26) $80,000 Beds: 5 Baths: 5.5 Sq. Feet: 4700Rental Registration #2026-L-0034 & 2026-V-0005. This grand compound bordering parkland is ... Property Details
Gracious Shelter Island with Pool
Priced at June ('26 - 26) $20,000; July ('26 - 26) $25,000 RENTED; August(LD) ('26 - 26, w/o LD $35k) $40,000 Beds: 5 Baths: 2Rental Registration #2025-L-0135. This classic Shelter Island country home was recently renovated by ... Property Details
