Beachfront vacation rentals in Shelter Island

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Top-rated beachfront rentals in Shelter Island

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Guest favorite

Cottage in North Fork

4.97 out of 5 average rating, 149 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Enjoy the designer kitchen with all new appliances, as well as a brand new bathroom, updated bedrooms and outdoor shower. This chic 2-bedroom, 1-bathroom home, which can sleep up to 5, has been designed with an eye for detail, style and relaxation. The master bedroom enjoys a queen sized bed that's perfect for 2 adults. The second bedroom can accommodate up to 3 people with a double bed for two people, and a single bed for one person. Only 80-miles from Manhattan, a 90-minute drive and close to the towns of Jamesport, Southold and Greenport, The Beach Cottage is the perfect summer escape. Stay on the property for swimming, paddle boarding, beach walks and BBQs or venture out to enjoy all the North Fork has to offer. Wine tasting at the French run winery Croteaux, lunch at the world class North Fork Table and Inn, shop at the many Organic Farms or explore the charming historic seaport village of Greenport, all short drives from the cottage. Upon request, Pets are allowed, for an extra fee of $200 per stay. Guests have access the entire property, including a private path to the beach. This stylish retreat is nestled on a private Soundfront beach at the end of a 7-acre property. Wine tasting at Croteaux, lunch at world-class North Fork Table and Inn, and the historic seaport village of Greenport are all within a short drive. The closest Jitney stop is Aquebogue or Riverhead. I am an Australian born designer that lives in NYC and has been renovating homes for the past several years. Our Flatiron loft in NYC was featured in Dwell Magazine, I designed the Upper West Side apartment for the founder & CEO of Soul Cycle, and my husband and I recently renovated our family's weekend beach house on the North Fork. I have a passion for turning houses into homes by bringing the clean, breezy and natural aesthetic, inspired by my homeland in Australia.

Guest favorite

Home in East Haven

4.96 out of 5 average rating, 132 reviews

The Breakaway - a waterfront gem.

Located next to historic Lighthouse Park, this Morgan Point, California-style bungalow overlooks a lighthouse and breakwater that protect New Haven Harbor. Prepare oceanfront dinners in your modern kitchen; relax to sunrises, sunsets, & the sound of waves. A quiet beach is steps from the door for swimming and kayaking. New Haven sights, restaurants, & nightlife are only minutes away. Picturesque coastline communities, local vineyards, breweries, fall foliage, & commuter rail to NYC are nearby.

Guest favorite

Home in North Fork

4.9 out of 5 average rating, 20 reviews

The Sandy Shack - Coastal Escape

Escape to your own private oasis at this charming beach house in Greenport. This beachfront home offers views of the ocean in every room. Inside, the living space gives plenty of natural light and sitting areas. The kitchen has everything you need to cook for family & friends. There are 4 beds to choose from, which can sleep 6 total. Outside, enjoy your own private beach as well as kayaks to use at your leisure. Located next to Greenport's best restaurants and wineries, book your stay today!

Superhost

Cabin in Shirley

4.85 out of 5 average rating, 137 reviews

A-Frame cabin with private beach & epic sunsets

Just a 1.5 hour drive from NYC, this home is the perfect beach getaway spot, with a few steps from the deck to the private beach with its beautiful view across the Great South Bay. Remote work with stunning water views through the wall of windows & in cold weather light a fire while sunlight floods the living space. Two queen bedrooms & bunk bed room sleeps 6 guests, great for families or a small gathering of friends. 5 min drive to ocean beach with great swimming & surfing at Smith Point.

Guest favorite

Home in Westhampton Beach

4.96 out of 5 average rating, 25 reviews

Dune Rd Village Waterfront Private Beach Access

Look no further for the perfect stay that offers an amazing location and sunset views, this stylish beach house is waterfront on Dune Road, Village of Westhampton Beach. The 1.2 acre property is located right on the bay with deep water dock and private boardwalk ocean beach access. 4 BR and 3 full BA, balcony and water views from each room. The home comes ready with high end furnishings by Hildreth's, Restoration Hardware, Serena & Lily, and Pottery Barn. Home come well stocked.

Guest favorite

Condo in North Fork

5 out of 5 average rating, 107 reviews

"Breathtaking Waterfront Water's Edge view"

" Breathtaking Waterfront Water's Edge condominium. Newly renovated! Relax and enjoy this beautiful, luxurious space. Suite B-204 accommodates 6 guests very comfortably. Two bedrooms, two bathrooms, living room with sofa (pull-out bed), kitchen area, eating area with chairs- all newly renovated. Located on the North Fork of Long Island, Cliffside Resort Condominiums in Greenport, New York." So many activities to choose from nearby and in the quaint village of Greenport!

Superhost

Rental unit in North Fork

4.83 out of 5 average rating, 6 reviews

Beach House - Apt 2

The Beach House - apt 2 is a 500 square foot alcove studio apartment, just 500 feet from the beach. Fully renovated in 2022 with an open layout and modern rustic style. It has updated appliances and a large smart tv. There is a cute restaurant conveniently located next door. It is on the first floor of a three family home. The patio and backyard area are shared with another apartment on the first floor. It is perfect for a peaceful and affordable getaway.

Guest favorite

Home in East Haven

4.94 out of 5 average rating, 52 reviews

Spectacular Waterfront Home on Private Sandy Beach

Beautiful two bedroom home located directly on the widest private beach in Connecticut is the perfect location for your next vacation. Newly built, this house has hardwood floors throughout, brand new appliances, washer and dryer, queen bed, two twin beds, fully furnished- including all kitchen necessities, central air, two decks, gas grill, plenty of parking, beach chairs, toys, kayak, paddle board, life vests, etc.

Guest favorite

Home in Montauk

4.97 out of 5 average rating, 73 reviews

Steps away from the Ocean

Our home with unobstructed ocean views has 5 bedrooms and 5 baths . It is located directly across the street from the ocean with a private path leading to the the most beautiful white sandy beach. We are within walking distance to the village of Montauk which is less than a mile away and we have bikes that are available for our guests to enjoy if they wish..

Guest favorite

Home in Old Lyme

5 out of 5 average rating, 7 reviews

Beach Front on Hawks Nest Beach (A)

Hawk's Nest Beach Home with Water Front Experience. Perfect for large family gatherings!! Pet Friendly Duplex home with two separate units. Door can connect the two units. Unit A -3 Bedrooms ( sleeps 6) - Full Bath -Parking for 4 vehicles, depending on size Large Private Beach. Includes outdoor shower and Grill

Guest favorite

Home in Montauk

4.97 out of 5 average rating, 37 reviews

Beach Front House

Welcome to this magnificent Montauk Beachfront Home with unspoiled panoramic ocean views from the whole top floor of this classic beach house. We are located in front of one of the quietest local beaches in town and less than a half mile stroll into the Village. 10 Guests 4 Bedrooms 6 Beds 2.5 Bathrooms