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

Place to stay in Amagansett

4.95 out of 5 average rating, 107 reviews

Walk-To-The-Beach House In The Dunes

This south-of-the highway artist retreat is just three minutes by foot to the ocean. Up to 4 bedrooms + a queen sleeping loft, 2 full en site indoor bathrooms, one half off common room, 3 outdoor showers and changing areas, downstairs 1000sqft workshop, new central AC, multi-room hi-fi, x2 two-person soaking hottubs. Fireplace, pellet, propane and charcoal grills, fiberoptic internet at blazing 500mbps! Only 6 mins to Montauk or Amagansett. Short walk to jitney stop. Weekly minimums in summer!

Guest favorite

Home in East Hampton

4.95 out of 5 average rating, 225 reviews

Private beach Historical House with large property

Entire three-story house. 3 large bedrooms and 3 FULL BATHROOMS on a very private, 2+acre wood lot on the bay in Historical East Hampton with private beach access. Fully renovated in 2018 with modern amenities while preserving the original charm. A/C and heating. Private upper floor with bedroom + sitting area for office and extra sleeping. Modern kitchen with island that opens to living room with fireplace. Walk through the secluded backyard to enjoy the amazing sunsets. Ideal for fishing.

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!

Guest favorite

Bungalow in Hampton Bays

5 out of 5 average rating, 124 reviews

Hamptons Waterfront- Great Location!

My place is right on the water with your own sandy beach. A quick walk to the restaurant and dining. No worries about having a drink and getting home. You’ll love my place because of the location and the ambiance. My place is good for couples, solo adventurers, business travelers, and families (with kids). Note: If this house does not have availability in June, July or August- please check out my other listing also a 2 bdrm/2 bath waterfront house (https://www.airbnb.com/h/canoebeachhousebh).

Guest favorite

Condo in North Fork

4.92 out of 5 average rating, 137 reviews

Beachside Waterview 2Br Condo w/ Pool in Greenport

Relax in a pristine 2Br condo with ocean & pool views. Our remodeled apartment is part of high-end development nestled on LI Sound, just minutes from downtown Greenport. Sip a glass of wine while watching sunset, catch some rays on the beach or deep in the pool. 2 bedroom condo with ocean view, beach, and pool (seasonal) Comfortably sleeps 6 Private beach access year-around Pool (seasonal) Functional kitchenette 2 bathrooms, all toiletries Linens and towels are provided Smart TV AC/Heat

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

Guesthouse in North Fork

4.95 out of 5 average rating, 127 reviews

Walk to Beautiful Beach in Heart of Wine Country

Enjoy bright, comfortable and modern home in the heart of North Fork wine and farm country located just a quick walk from a gorgeous Peconic Bay beach with tennis/pickleball courts, volleyball and playground right on the beach. You'll have easy and quick access to the best of the east end: beautiful beaches, boating, fishing, fine and casual dining, vineyards, wineries, breweries, farms and farm stands offering fresh local produce, antique and local shops.

Superhost

Home in North Fork

4.9 out of 5 average rating, 200 reviews

Greenport Beach House

Nestled steps from the beach, and all that Greenport and the North Fork has to offer, this exquisitely charming 3 bedroom 2 bathroom waterfront home is absolutely delightful.. You’ll love my place because of the views, the location, the people, the ambiance, the outdoors space, and the Saltwater pool.. My place is good for couples, solo adventurers, business travelers, families (with kids), groups, and furry friends (pets).