Rental Listings
Shelter Island Close Proximity to Everything
Priced at MD-LD ('23 - 23) $34,000; July ('23 - 23) $12,000; August(LD) ('23 - 23) $15,000; September ('23 - 23) $11,000 Beds: 3 Baths: 1 Sq. Feet: 1600Rental Registration# 19L-2133. This fresh and updated upside down modern on .75 acre is located ... Property Details
Shelter Island Beach House with Pool
Priced at MD-LD (05/29/23 - 09/04/23) $67,000; June ('23 - 23) $15,000; July/August(LD) (07/01/23 - 09/04/23) $55,000; July ('23 - 23) $25,000; August(LD) ('23 - 23) $30,000; Beds: 3 Baths: 2 Sq. Feet: 1424Rental Registration #2021-L-20. Enjoy your summer stay at this pristine Shelter Island 3 bedroom, 2 ... Property Details
Shelter Island Sleek and Chic Waterfront
Priced at June/July (05/26/23 - 07/31/23) $90,000; June (05/26/23 - 06/30/23) $40,000 Beds: 4 Baths: 2.5 Sq. Feet: 3091Rental Registration #19L-0052. This resort-style waterfront modern offers everything you could hope ... Property Details
Quaint Shelter Island Cottage
Priced at June ('23 - 23) $20,000; July ('23 - 23) $35,000; August ('23 - 23) $39,000 Beds: 3 Baths: 2 Sq. Feet: 2173Rental Registration #2022-L-0050. This beautiful and unique home on 3 + acres offers a very private ... Property Details
Stunning Shelter Island Bay Front with Dock and Pool
Priced at June ('23 - 23) $90,000; July ('23 - 23) $100,000; August(LD) ('23 - 23, w/o LD $115k) $130,000 Beds: 5 Baths: 6 Sq. Feet: 6500Rental Registration #20L-0138. Simply put, Shelter Island still remains an undiscovered paradise ... Property Details
Shelter Island Sleek with Pool
Priced at May ('23 - 23) $15,000; June ('23 - 23) $15,000; July ('23 - 23) $35,000; July/August(LD) (07/01/23 - 09/04/23) $70,000; August(LD) ('23 - 23) $35,000 Beds: 2 Baths: 3 Sq. Feet: 1300Rental Registration #20-L-0032. Located within close proximity to sandy beach, this recently ... Property Details
Shelter Island Tranquil Creekfront Farmhouse with Pool
Priced at June ('23 - 23) $14,000; July ('23 - 23) $30,000 Beds: 5 Baths: 4.5 Sq. Feet: 2850Rental Registration #2021-L-48. Located within close proximity to ferry, restaurants and marina, ... Property Details
Shelter Island Sweet Traditional with Pool
Priced at April ('23 - 23) $6,500; May ('23 - 23) $17,000; June ('23 - 23) $24,000; Custom (07/01/23 - 07/31/23) $38,000; Custom (07/15/23 - 07/29/23) $19,000; August(LD) ('23 - 23) $42,000 Beds: 4 Baths: 3.5 Sq. Feet: 2004Rental Registration #2022-L-0004. This traditional with four-bedrooms, three and one-half bathrooms ... Property Details
Shelter Island Waterfront with Pool
Priced at July ('23 - 23) $35,000; August(LD) ('23 - 23) $37,000 Beds: 3 Baths: 4 Sq. Feet: 3160Rental Registration #0012. Some of the most spectacular sunsets can be enjoyed from this spacious ... Property Details
Shelter Island Blufftop with Sandy Beach
Priced at Custom (05/26/23 - 09/04/23) $50,000; June ('23 - 23) $15,000; July ('23 - 23) $18,500; July/August(LD) ('23 - 23) $35,000; August(LD) ('23 - 23) $22,500 Beds: 3 Baths: 2 Sq. Feet: 1262Rental Registration #2021-L-02. This long time favorite is in one of the most dramatic spots on Ram ... Property Details
Shelter Island Close Proximity to Beach
Priced at MD-LD ('23 - 23) $50,000 RENTED; June ('23 - 23) $10,000 RENTED; July ('23 - 23) $17,000 RENTED; August ('23 - 23) $23,000 RENTED Beds: 4 Baths: 2 Sq. Feet: 1457Rental Registration #20-L-0002. This fresh Silver Beach cottage, located within close proximity to ... Property Details
Pristine Shelter Island Bay View with Dock Access
Priced at July ('23 - 23) $28,000; August(LD) ('23 - 23, w/o LD $30k) $35,000 Beds: 3 Baths: 2 Sq. Feet: 1608Rental Registration #2021-L-91. This recently renovated ranch has a sunny living room, kitchen with ... Property Details
Classic and Chic on Shelter Island
Priced at Extended Season (10/01/22 - 04/30/23) $3,500; Custom (05/15/23 - 10/18/23) $74,000 Beds: 4 Baths: 3 Sq. Feet: 2618Rental Registration #20-L-0122. Stylish and spacious, with an interesting mix of old world ... Property Details
Shelter Island Modern Close to Beach
Priced at June ('23 - 23) $17,000; July ('23 - 23) $30,000; August(LD) ('23 - 23, w/o LD $30k) $35,000 RENTED Beds: 4 Baths: 4 Sq. Feet: 3280Rental Registration #2021-L-98. Within close proximity to a wide sandy bay beach, this pristine four ... Property Details
Lush and Lovely Shelter Island with Pool
Priced at August(LD) ('23 - 23, w/o LD $35k) $38,000 Beds: 4 Baths: 4 Sq. Feet: 2424Rental Registration #2022-L-0084. Located a half block from sandy beach, this deer free property has ... Property Details
Shelter Island 180-Degree Water Views of Crescent, Sunset Beach
Priced at Custom (06/01/23 - 09/04/23) $58,750; July/August(LD) ('23 - 23) $42,500 Beds: 4 Baths: 1.5 Sq. Feet: 1456Rental Registration #20-L-0004. This delightful water view cottage is a stone's throw from Sunset ... Property Details
Shelter Island Traditional with Deep Water Dock
Priced at MD-LD ('23 - 23) $82,500 RENTED; June ('23 - 23) $15,000 RENTED; July ('23 - 23) $30,000 RENTED; August(LD) ('23 - 23) $31,500 RENTED Beds: 3 Baths: 3 Sq. Feet: 2200Shelter Island, NY Vacation Rental Rental Registration #19S-0012. This sun filled traditional is ... Property Details
Hilltop Traditional with Pool Close Proximity to Beach
Priced at March ('23 - 23) $5,000; April ('23 - 23) $5,000; June (05/26/23 - 06/30/23) $22,000; July ('23 - 23) $25,000; August(LD) ('23 - 23) $28,000; September ('23 - 23) $15,000 Beds: 3 Baths: 2 Sq. Feet: 2962Rental Registration #20-L-0086. Located within close proximity to Sunset Beach, ferry and golf, this ... Property Details
Shelter Island Pristine Waterfront Compound with Pool and Dock
Priced at MD-LD ('23 - 23) $284,000 RENTED; June ('23 - 23) $83,000 RENTED; July ('23 - 23) $96,000 RENTED; August ('23 - 23) $106,000 RENTED Beds: 5 Baths: 5 Sq. Feet: 3000Rental Registraton #2021-L-96. In one of the most pristine natural settings on Shelter Island, ... Property Details
Quaint and Convenient Shelter Island
Priced at June ('23 - 23) $7,700; July ('23 - 23) $8,800; August(LD) ('23 - 23) $11,550 Beds: 2 Baths: 2 Sq. Feet: 892Rental Registration #2023-L-0007. A delightful two-bedroom, two-bath cottage in Shelter Island's ... Property Details
