Shelter Island, NY Homes for Rent

This newly updated ranch house on Tuthill Drive (a private road on Big Ram Island) has been reimagined with the greatest attention to detail and quality. The open plan connects a spacious sun and (high fidelity) TV room with living room (and wet bar),cook's kitchen, and full dining room Three bedrooms include a private guest suite (with steam shower)primary and secondary bedrooms both

In one of the most sought after locations on Shelter Island, this original waterfront cottage has the most beautiful water views overlooking Coecles harbor to Gardiners Bay, with full sunlight from Sunrise to Sunset. This 4 bedroom 2 bath property sits at the end of a long winding driveway providing great privacy. There has been a new kitchen renovation now providing water views while cooking.

Welcome to Sandpoint, an exclusive Shelter Island retreat recently built on 1.4 acres, just a stone's throw from a sandy beach and across from a 12-acre preserve. This stunning home features five bedrooms, including two master suites and one room with twin beds. Sunlit and spacious, the heart of the home is a well-equipped kitchen with an oversized island overlooking a large pool and landscaped

Within close proximity to sandy Hay Beach, this immaculate 4 bedroom, 4 bath cedar shingled three-level modern has the spirit of living in a birds nest with sliding glass doors and porches everywhere overlooking cherry trees and wrap around deck, bay breezes blow throughout gently. The kitchen is a chef's delight, with granite counters, maple cabinets, Viking stove, Monogram refrigerator, Bosch

Built in 1929, this spectacular water front home on West Neck Bay is enjoyed from this 3-bedroom/ 3 bathroom CAC sunny home. Spacious rooms, a studio cottage with half bath and a dock with deepwater mooring complete the picture for the summer season. RR# 2021-L-0158 [[Rental Registration # 2024-L-0004]]

This clean and modern harborfront home is located in an area that features glorious sunsets. There are lovely gardens and shade trees with meditation areas to read or relax in, and the main home offers an open floor plan, with an L-shaped living room that maximizes views of the water, a fireplace for chilly nights, dining area overlooking the water, and efficient kitchen. There is a first floor

Adorable 2 bedroom cottage located in the center of it all. This remodeled cottage features all new kitchen, floors and windows. Large sunlit living room with dining area and fireplace. A wonderful sunroom off the front of the house features afternoon sun. A terrific bargain for July and August. Easy to view. [[Rental Registration # 2025-L-0087]]

What a great place for a summer vacation! This stunning home is located on a beautifully landscaped, very private, .92 fenced and gated acre within easy distance of Wades Beach, Fresh Pond, library, and restaurants. That is if you can tear yourself away from the comforts of home. A covered front porch opens to a great room with living and dining areas, fireplace and glass doors to the back deck

Turn of the Century Shelter Island Victorian just minutes from shops, restaurants, tennis, beach and ferry yet nestled on a quiet little Heights street across from a small peaceful park. Absolutely charming with comfortable living room which opens to a wonderful covered wrap porch and ample dining room. The eat-in-kitchen has access to a back porch adjacent to grilling area, half bath and main

This home has been thoughtfully designed creating spaces for complete comfort and relaxing whether alone or entertaining large groups of friends. Detailed with the highest quality and craftsmanship throughout . Starting with the extensive outdoor spaces all accessible from the main rooms of the house , the pool area has generous lounging areas including and outdoor kitchen , leading onto the

This open and bright 3 bedroom 2 Bath with heated pool is the perfect summer escape. Enjoy strolls on beautifully preserved Menhaden Beach from this quiet enclave. The house features central air, outdoor shower, finished lower level, comfortable outdoor areas with decks and patios, Pet considered [[Rental Registration # 2023-L-205]]

Flooded with sunlight, this beautifully furnished 4 bed 3 bath home offers ultimate privacy on 3/4 acres. Completely updated with all new bathrooms and kitchen. The Chef's kitchen is designed with a spacious dining area for large gatherings. Primary en-suite has its own deck leading to the the pool and back garden. The other bedrooms are located at opposite ends of the house offering complete