Rental Listings
Gracious Shelter Island with Pool
Priced at July ('26 - 26) $25,000 RENTED; August ('26 - 26) $35,000 RENTED 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
Shelter Island Scandinavian with Pool and Guest House
Priced at July ('26 - 26) $35,000; August (08/01/26 - 08/15/26) $20,000 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 July ('26 - 26) $35,000 RENTED; Custom (08/28/26 - 09/07/26) $8,000; Custom (09/08/26 - 09/30/26) $8,000; October ('26 - 26) $8,000; November ('26 - 26) $8,000; December ('26 - 26) $8,000; January ('27 - 27) $8,000; February ('27 - 27) $8,000; March ('27 - 27) $8,000; April ('27 - 27) $8,000; May ('27 - 27) $8,000; June ('27 - 27) $8,000 Beds: 2 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) ('26 - 26, w/o LD $16k) $18,000 Beds: 4 Baths: 3 Sq. Feet: 2400Rental Registration #2026-L-0044. This sun filled one level cottage is located within a stone's ... Property Details
Shelter Island Harborfront Farmhouse
Priced at June ('26 - 26) $15,000 RENTED; July ('26 - 26) $30,000 RENTED; August ('26 - 26) $35,000 RENTED; September ('26 - 26) RENTED 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 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
Shelter Island Spacious Traditional with Pool Close to Beach
Priced at Weekly (08/23/26 - 09/05/26) $10,800 Beds: 5 Baths: 3.5 Sq. Feet: 2552Rental Registration #2026-L-0080. Enjoy your summer at this spacious traditional with plenty of room ... 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
Shelter Island Adorable Bungalow near Marina
Priced at July ('26 - 26) $8,500; August(LD) ('26 - 26) $9,500 Beds: 3 Baths: 2 Sq. Feet: 1200Rental Registration #2025-L-0042. Located in Montclair Colony is this charming cottage with three ... Property Details
Newly renovated 1911 Historic Estate with Pool on 6 Acres
Priced at 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 home combines old world charm with ... Property Details
Shelter Island Beach House with Pool
Priced at July ('26 - 26) $30,000; August(LD) ('26 - 26) $35,000 Beds: 3 Baths: 2 Sq. Feet: 1424Enjoy your summer stay at this pristine Shelter Island 3 bedroom, 2 bath cottage with beautiful ... Property Details
Ram Island Beach House with Sandy Beach and Dock
Priced at July ('26 - 26) $27,500; August (LD) ('26 - 26) $30,000 Beds: 3 Baths: 2 Sq. Feet: 1842Rental Registration #2024-L-0117. Feel at one with the sea at this newly renovated Beach House ... Property Details
Shelter Island Waterfront with Pool and Dock
Priced at MD-LD ('26 - 26) $100,000; July ('26 - 26) $40,000; August(LD) ('26 - 26) $50,000; September ('26 - 26) $20,000 Beds: 4 Baths: 2 Sq. Feet: 2200Rental Registration #2026-L-0003. Charming waterfront cottage offers views of the harbor from nearly ... Property Details
Farmhouse with Pool
Priced at 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
Shelter Island Modern Close to Beach
Priced at Two Weeks (07/01/26 - 07/14/26) $20,000; Two Weeks (07/15/26 - 07/31/26) $20,000 Beds: 4 Baths: 4 Sq. Feet: 2120Rental Registration #2026-L-0002. Within close proximity to a wide sandy bay beach, this pristine ... Property Details
Lush and Lovely Shelter Island with Pool
Priced at Custom (07/17/26 - 07/31/26) $21,000; Two Weeks (08/01/26 - 08/14/26) $21,000 Beds: 4 Baths: 4 Sq. Feet: 2424Rental Registration #2026-L-0030. Located a half block from sandy beach, this deer free property has ... Property Details
Shelter Island Getaway with Stunning 180-degree Waterfront Views
Priced at July/August ('26 - 26) $24,500; July ('26 - 26) $13,500; August(LD) ('26 - 26) $15,500 Beds: 4 Baths: 1.5 Sq. Feet: 1456Rental Registration #2026-L-0013. A romantic and secluded summer getaway. Enjoy a front row seat to ... Property Details
Shelter Island Traditional with Deep Water Dock
Priced at Custom (05/22/26 - 07/31/26) $65,000; MD-LD ('26 - 26) $90,000; July ('26 - 26) $35,000; July/August(LD) ('26 - 26) $70,000; August(LD) ('26 - 26, w/o LD $35k) $43,000 Beds: 3 Baths: 3 Sq. Feet: 2200Shelter Island, NY Vacation Rental Rental Registration #2025-L-0137. This sun filled traditional is ... Property Details
Shelter Island Cottage Close Proximity to Sandy Beach
Priced at June/July ('26 - 26) $15,000; Two Weeks (06/01/26 - 07/31/26) $5,000; July ('26 - 26) $10,000 Beds: 3 Baths: 1.5 Sq. Feet: 1935Rental Registration #2025-L-0118. New to the rental market! This well maintained, sunny cottage is ... Property Details
