Rental Listings
Timeless Charm on Shelter Island
Priced at July ('26 - 26) $35,000; August(LD) ('26 - 26) $40,000 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) $45,000 RENTED; August(LD) ('26 - 26, w/o LD $48k) $50,000 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 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) $28,000; August(LD) ('26 - 26) $31,000 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; Two Weeks (06/01/26 - 06/14/26) $14,000; Custom (07/15/26 - 08/02/26) $25,000; August(LD) ('26 - 26, w/o LD $42k) $47,000 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 Elegant Bayfront with Deepwater Dock
Priced at July ('26 - 26) $48,000; Two Weeks (08/01/26 - 08/14/26) $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 Picturesque Farmhouse with Pool
Priced at July ('26 - 26) $30,000 Beds: 8 Baths: 3 Sq. Feet: 2720Rental Registration #2025-L-0014. Located a short distance from Heights, ferry, shops, fine dining ... Property Details
Sweet and Sunny Shelter Island with Pool
Priced at July ('26 - 26) $50,000; August(LD) ('26 - 26, w/o LD $55k) $60,000 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
Gracious Shelter Island with Pool
Priced at MD-LD ('26 - 26) $75,000; June ('26 - 26) $20,000; July ('26 - 26) $25,000; August ('26 - 26) $35,000 Beds: 5 Baths: 2Rental Registration #2025-L-0135. This classic Shelter Island country home was recently renovated by ... Property Details
Shelter Island Charming Harbor Front Cottage
Priced at July ('26 - 26) $25,000; August(LD) ('26 - 26) $25,000 Beds: 3 Baths: 3 Sq. Feet: 2209Rental Registration #2026-L-0019. Turn of the century cottage with southern views onto the harbor ... Property Details
Chic Shelter Island Barn with Pool and Day Dock
Priced at April ('26 - 26) $5,000; Custom (06/01/26 - 06/15/26) $25,000; July ('26 - 26) $35,000 RENTED; Two Weeks (08/01/26 - 08/31/26) $15,400; August (LD) ('26 - 26, w/o LD $25k) $30,000; Weekly (08/30/26 - 09/07/26) $8,000 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
Shelter Island Harborfront Farmhouse
Priced at July ('26 - 26) $30,000; August ('26 - 26) $35,000 Beds: 3 Baths: 1 Full, 1 Half Sq. Feet: 1536Rental Registration #2024-L-0029. This classic Shelter Island harborfront farmhouse was built in ... Property Details
Bayview Contemporary Shelter Island
Priced at Weekly (09/01/25 - 06/07/26) $5,500; Custom (06/01/26 - 06/18/26) $7,500; Custom (06/17/26 - 06/30/26) $10,000; July ('26 - 26) $21,000; Two Weeks (07/07/26 - 07/21/26) $10,000; Weekly (07/22/26 - 07/29/26) $5,500; August(LD) ('26 - 26) $26,000; Two Weeks (08/17/26 - 08/31/26) $11,500; September ('26 - 26) $14,000; Two Weeks (09/01/26 - 09/30/26) $7,500 Beds: 4 Baths: 3 Sq. Feet: 2600Rental Registration #2025-V-002. This sunny Contemporary with slices of water views has loads of ... Property Details
Cheery Renovated Shelter Island Farmhouse near Marina
Priced at Custom (06/20/25 - 07/22/25) $12,000 RENTED; Year Round (10/01/25 - 09/30/26) $62,000 RENTED Beds: 4 Baths: 2.5 Sq. Feet: 2052Rental Registration #2023-L-0172 & 2024-V-0023. This sun filled farmhouse has been recently ... Property Details
Newly renovated 1911 Historic Estate with Pool on 6 Acres
Priced at June ('26 - 26) $30,000; Two Weeks (06/01/26 - 06/30/26) $15,000; Two Weeks (07/13/26 - 07/31/26) $25,000; August ('26 - 26) $50,000; Two Weeks (08/01/26 - 08/31/26) $25,000; Two Weeks (08/24/26 - 09/07/26) $30,000 Beds: 6 Baths: 4.5 Sq. Feet: 2790Rental Registration #2025-L-0031. This newly renovated 1911 plantation style home combines old world ... Property Details
Farmhouse with Pool
Priced at Winter (11/01/25 - 04/30/26) $3,500; Custom (05/01/26 - 05/25/26) $4,000; Weekly (05/22/26 - 06/14/26) $4,000; Weekly (08/16/26 - 09/07/26) $4,200; Custom (08/16/26 - 09/07/26) $9,500 Beds: 4 Baths: 2.5 Sq. Feet: 2522Rental Registration #2025-L-0107. New to the Market. Hidden behind tall privet hedges with wide ... Property Details
