Shelter Island, NY, USA apartments for rent

Wake up each morning to the sweet sounds of birdsong in this charming 4-bedroom, 2-bath, nestled amongst rolling hills. Located.6 miles from coveted Wades Beach and Mashomack Preserve. This secluded property feels like a private sanctuary, surrounded...

In one of the most sought after locations on Shelter Island, this original waterfront cottage has the most beautiful waterviews overlooking Coecles harbor to Gardiners Bay, with full sunlight from Sunrise to Sunset. This 4 bedroom 2 bath property sit...

Short term rental! Available August 17 to September 1 at$20, 0000.This 4 Bedroom waterfront house creates incredible freedom between the insides and outside living areas. The expansive covered porch overlooking the water is a tranquil place to relax ...

Tucked on a hill and hidden from view, this immaculate, traditional home on 1.2 acres overlooking Fresh Pond has a sense of seclusion and tranquility, with prevailing southwest breezes and sunsets as a welcome backdrop. Well thought-out in every way,...

Relax on Shelter Island. Enjoy a central location close to town and amenities within a short bike ride of Wades Beach, golf, tennis, and local oysters. Under 2 miles to Sunset Beach, The Chequit, and Leon restaurants, Marie Eiffel market, Sylvester M...

Amazing Waterfront Views.Awaken to bird songs and swans gliding across the water. Sip coffee on the deck while planning the days adventures. Paddle board or kayak across the creek and have a swim at Wade’s beach. Come back and shower in the glori...

19L-0033Completely rebuilt 4 bedroom, 3 bath home just a stone's throw from Wade's Beach. Featuring an open plan which includes a living room with fireplace and beamed ceiling, dining area, kitchen with all new appliances and wonderful glassed porch ...

This newly renovated Shelter Island gem features green lawns, private beach and dock. Newly renovated, the house is clean and airy with beautiful light from windows overlooking West Neck Harbor. The kitchen opens onto waterside deck for sunset dinner...

You can walk to the beach from this attractive home that comfortably sleeps 7. Enjoy cocktails and outdoor dining on the second floor wrap around deck. The second floor great room makes entertaining fun and relaxing. The kitchen, fully equipped with ...

Located a few doors from beach and boating access, this lovely vacation home has an airy open design with vaulted ceilings in the living room, fireplace, dining area and sun room. All have access to a wrap deck with open area for sunbathing and also ...

This family friendly private three-bedroom, two bathroom Silver Beach ranch house is perfect for any season. Enjoy the pool, covered porch and walking distance to beaches and bays, the large chef's kitchen and comfy living room with fireplace in cool...

This house is the summer retreat you have been looking for. Centrally located down a private lane you will enjoy extraordinary views of the creek from the poolside patio. Private dock on this waterfront property for all the summer activities, just fe...

This original 4 bedroom Shelter Island Farmhouse is located on the perfect 3.4 acre setting. offering complete privacy. A beautiful large property overlooking a nature preserve is the perfect place to slow down and hang out with family and friends, f...

Feel like you are on a luxury cruise ship! Beautiful Shelter Island three bedroom/ three bathroom home. Large living room/dining room, two car garage. The home has unobstructed expansive views of Peconic Bay. This bright and airy house faces ...

Enjoy this newly renovated home on Shelter Island. A gorgeous, well-stocked gourmet kitchen with vaulted ceiling great room allows the chef(s) to be a part of the fun. Sliders out to the pool and tons of outdoor seating provide plenty of options for ...

Just a few minutes from Wades Beach is this private park-like enclave with a charming 2+ bedroom, 1.5 bath shingled home, brand new heated gunite pool and beautiful new cottage with BR, bath, kitchenette, living room and dining area. This fully fence...

Absolutely beautiful, charming, and pristine! Totally renovated home in one of the quietest neighborhoods on Shelter Island. Stunning design and tastefully decorated throughout. Recently renovated and furnished impeccably with over2, 700sq ft of livi...

4,000 sq ft waterfront family home on 3 acres. Plenty of space for the whole family! Our home maintains the traditional charm of a late 19th century farmhouse. If you love vintage houses with an elegant, boho feel, a huge porch to gather with friends...

Adorable getaway cottage with 2 bedrooms, bath, living room with dining area, fully equipped kitchen, covered front porch and big backyard with patio seating area. Just updated, furnished and available for summer and winter rental. Near Coecles Harbo...

When an artist makes a home Serena Dugan, Co-Founder of SerenaandLily has completed her renovation of 37 Tuthill Drive, Shelter Island. This property is a robust representation of Serena's vision as an artist and a designer. Each detail was ca...

2025 Rates: June$30, 000,July$60, 000,July-August$125, 000and August-Labor Day$65, 000.This stunning two-story home sits on 3.44 acres of beautiful lawns and trees, featuring a circular driveway and a double-arched covered porch with bluestone patio....

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 ...