Rental Listings
Shelter Island Sleek and Chic Waterfront
Priced at MD-LD ('21 - 21) $100,000 RENTED Beds: 4 Baths: 2.5 Sq. Feet: 3091Rental Registration #19L-0052. This resort-style waterfront modern offers everything you could hope ... Property Details
Stunning Bay Front
Priced at July ('21 - 21) $100,000; August(LD) ('21 - 21) $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 ('21 - 21) $9,000 RENTED; June ('21 - 21) $9,000 RENTED; July ('21 - 21) $20,000 RENTED; July/August(LD) (07/01/21 - 09/06/21) $45,000 RENTED; August(LD) ('21 - 21) $22,000 RENTED Beds: 3 Baths: 3 Sq. Feet: 1300Rental Registration #20-L-0032. Located within close proximity to sandy beach, this recently ... Property Details
Wades Beach Chic Cottage on the Dunes
Priced at Winter (01/01/21 - 04/30/21) $6,000; MD-LD ('21 - 21) $75,000; June ('21 - 21) $20,000; July ('21 - 21) $25,000; August(LD) ('21 - 21) $35,000; December ('21 - 21) $6,000 Beds: 3 Baths: 2 Sq. Feet: 1080Rental Registration #20L-0055. This fresh and chic beach cottage promises a fun summer on the dunes. ... Property Details
Shelter Island Sweet Traditional with Pool
Priced at January ('21 - 21) $9,000; February ('21 - 21) $9,000; March ('21 - 21) $9,000; April ('21 - 21) $9,000; May ('21 - 21) $9,000; June ('21 - 21) $18,000; July ('21 - 21) $28,000; August(LD) ('21 - 21, w/o LD $32,000) $36,000 Beds: 4 Baths: 3.5 Sq. Feet: 2004Rental Registration #20-L-0001. This traditional with four-bedrooms, three and one-half bathrooms ... Property Details
Shelter Island Blufftop with Sandy Beach
Priced at MD-LD (05/01/21 - 09/06/21) $60,000; June ('21 - 21) $20,000; July ('21 - 21) $20,000; August(LD) ('21 - 21) $25,000 Beds: 3 Baths: 2 Sq. Feet: 1262Rental Registration #19L-0013. This long time favorite is in one of the most dramatic spots on Ram ... Property Details
Shelter Island Close Proximity to Beach
Priced at Year Round (09/08/20 - 09/08/21) $52,000 RENTED Beds: 4 Baths: 2 Sq. Feet: 1457Rental Registration #20-L-0002. This fresh Silver Beach cottage, located within close proximity to ... Property Details
Waterfront Contemporary with Pool on Shelter Island
Priced at MD-LD ('21 - 21) $110,000; June ('21 - 21) $25,000; June/July ('21 - 21) $75,000; July ('21 - 21) $45,000; August(LD) ('21 - 21) $45,000 Beds: 4 Baths: 3.5 Sq. Feet: 3500Shelter Island Home for Rent Rental Registration #19L-0018. Phenomenal views of Gardiner's Bay ... Property Details
Classic and Chic on Shelter Island
Priced at Winter (01/01/21 - 04/30/21) $32,000 Beds: 4 Baths: 3 Sq. Feet: 2618Rental Registration #20L-0122. Stylish and spacious, with an interesting mix of old world ... Property Details
Shelter Island Modern Close to Beach
Priced at June ('21 - 21) $18,000; July ('21 - 21) $25,000 RENTED; August ('21 - 21) $26,000 RENTED; Custom (09/07/21 - 09/30/21) $10,000 Beds: 4 Baths: 4 Sq. Feet: 3280Rental Registration #19L-0106. Within close proximity to a wide sandy bay beach, this pristine four ... Property Details
Lush and Lovely Shelter Island with Pool
Priced at July ('21 - 21) $23,000; August(LD) ('21 - 21, w/o LD $35k) $38,000 Beds: 4 Baths: 4 Sq. Feet: 2424Rental Registration #20-L-0129. Located a half block from sandy beach, this deer free property has ... Property Details
Shelter Island Sunset Cottage
Priced at Two Weeks (06/01/21 - 07/31/21) $10,875; June ('21 - 21) $14,250; Custom (06/01/21 - 09/06/21) $41,500; July (07/01/21 - 07/31/21) $17,000; July/August (07/01/21 - 09/06/21) $32,250; August(LD) (08/01/21 - 09/06/21) $19,500 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 August(LD) ('21 - 21) $25,000 Beds: 3 Baths: 3 Sq. Feet: 2200Shelter Island, NY Vacation Rental Rental Registration #19S-0012. This sun filled traditional is ... Property Details
Shelter Island Cottage Close Proximity to Sandy Beach
Priced at July ('21 - 21) $7,000; August(LD) ('21 - 21) $10,000 Beds: 3 Baths: 1.5 Sq. Feet: 1935Rental Registration #19L-0105. New to the rental market! This well maintained, sunny cottage is ... Property Details
Hilltop Traditional with Pool Close Proximity to Beach
Priced at June (05/28/21 - 06/30/21) $20,000; July ('21 - 21) $25,000; August(LD) ('21 - 21) $35,000 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 Two Weeks (01/02/21 - 05/27/21) $22,500; Custom (05/28/21 - 06/30/21) $82,500; July ('21 - 21) $96,000; August(LD) ('21 - 21) $111,500; Weekly (12/10/21 - 01/01/22 $10,800 Beds: 5 Baths: 5 Sq. Feet: 3000Rental Registraton #19L-0058. In one of the most pristine natural settings on Shelter Island, ... Property Details
Quaint and Convenient Shelter Island
Priced at June ('21 -21) $7,000; Two Weeks (07/01/21 - 07/14/21) $4,000; Custom (08/15/21 - 09/06/21) $4,500; Custom (09/01/21 - 09/30/21) $6,500; Winter (10/01/21 - 10/31/21) $5,000 Beds: 2 Baths: 2 Sq. Feet: 892Rental Registration #19L-0045. A delightful two-bedroom, two-bath cottage in Shelter Island's ... Property Details
Shelter Island Heights Contemporary
Priced at June ('21 - 21) $8,000; July ('21 - 21) $13,000; Two Weeks (08/01/21 - 09/06/21) $18,000 Beds: 3 Baths: 2 Sq. Feet: 1584Rental Registration #19L-0114. Located a stone's throw from Shelter Island Country Club, Crescent ... Property Details
Shelter Island Spacious Traditional with Pool
Priced at Custom (05/24/21 - 05/31/21) $15,000; Weekly (06/01/21 - 06/26/21) $10,000; Custom (06/01/21 - 06/26/21) $35,000; Weekly (08/07/21 - 09/06/21) $15,000; Cabana: Two Weeks (08/01/21 - 09/06/21) $30,000 Beds: 7 Baths: 6.5 Sq. Feet: 5643Rental Registration #'s 022-2017 / 19S-0010. First offering! This stunning traditional located a ... Property Details
Summer Beach Cottage on Shelter Island
Priced at January (01/15/21 - 01/31/21) $1,500; February ('21 - 21) $3,000; March ('21 - 21) $3,000; April ('21 - 21) $3,000; July/August(LD) ('21 - 21) $20,000; Two Weeks (07/01/21 - 09/06/21) $5,000; July ('21 - 21) $11,000 Beds: 2 Baths: 1 Sq. Feet: 700Shelter Island Summer Beach Cottage for Rent Rental Registration #19L-0029. Located within close ... Property Details
